should I ask out an employee at a store where I shop?

by Alison Green on July 24, 2015

A reader writes:

I am an adult who has a crush on someone (also an adult) who works in retail. He may be a manager. He’s rung me up (cash register, not phone) multiple times and we’ve done the usual chitchat, and when I’m at his store he very obviously stares at me and often pops up in the areas that I’m shopping in. Granted, this could mean nothing, but it’s impossible for me to know what’s going on since the only place that I ever see him is in this store. I’d like to find out what he’s thinking, but it’s kind of awkward since since he’s at work.

If you were interested in a customer, what would you do about it? What would think if one of your employees asked out a customer? What do you think about customers asking you out? And what do you think about customers asking out your employees? I’m assuming that some places have policies about this sort of thing but have no idea about the policies at this store. At any rate, I don’t want to do anything to make him uncomfortable, and if things go awry then I’ll most likely try to avoid him or stop shopping at this place altogether, which would be really inconvenient, so would really appreciate your advice.

Well, the tricky thing about asking out someone in a customer service position is that their job requires them to be nice to you. Because of that, it can be easy to mistakenly misinterpret them doing their job (being nice to you) as social/romantic interest. And of course, a lot of people would prefer not to field come-ons while they’re working.

That doesn’t mean that you should never do it or that it never works out, but it does mean that if you’re going to do it, it’s key to approach it in a low-key way that makes it really, really easy for the person to say no. It also means that you have to go out of your way to make them comfortable if they do say no (no signs of resentment or bitterness or other weirdness), because after all you did take the risk of asking someone out in their place of work.

There’s also no way to guarantee it’ll go smoothly (he could say no, or you could go out and it could be disastrous), so if that’s going to keep you from shopping there, you’ve got to decide which you want more: the possibility of a date with him or the certainty that you can continue comfortably going to that store.

That, of course, is why lots of managers would rather customers not ask out their employees — it’s a good way to lose customers who then feel too awkward to return.

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{ 274 comments }

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      1. And we danced from the ocean*

        I’ve seen this debated in a number of places around the ‘net over the years. You’ve got the people who say “Please no! It gets so old!” You’ve got the people who say “the waiter seemed friendly, so I gave him my number, and we’ve been married 30 years now”. And the people who are psychic: “you’re misunderstanding their friendly customer service smile as interest”. And all kinds of stuff in-between.

        OP: I think most people can tell when there is some genuine interest going on. If you think he’s interested, write your phone/text number down and as you’re leaving, talk with him a bit, smile, give your number to him and say “if you ever want to talk outside of work, call me or text me” – then leave. If you don’t hear from him in a week – oh well. (And even then it might simply have been bad timing: he got in a car accident, etc)(or, sadly, he may already have a GF).

        If he calls, you know what to do. Although again, sadly, he still might have a GF. (Helpful hint: if he’ll only text and won’t talk on the phone, that is often a sign that he has an SO of some kind).

        It kills me how some people react over this, though: “don’t do it!” “How dare you inflict yourself on this poor sales assistant!” etc. Like you’re causing major pain to someone by giving them your #. You’re not.

        1. anonanonanon*

          It may not be inflicting major pain, but it’s still annoying and uncomfortable to have to deal with that at work, especially if you’re in a position where you can’t walk away after the encounter. You’d be surprised by how many people do misinterpret friendliness for genuine interest.

          1. Nikki T*

            That’s why the OP should say it cheerfully, quietly, quickly, hand the card over and exit. Then wait a couple of weeks before returning and never mentioning it again if you don’t hear back.

            Keep in mind, if you do date, you may have to limit your time at this store anyway….

          2. Stranger than fiction*

            Hmm I’m on the fence here. I worked in restaurants for years and later on in customer service and sales. At restaurants this happened a lot and I was never offended and it was only slightly awkward for a moment and a simple ” I have a boyfriend” always worked as a “no” whether I had one or not. Luckily I never got any creepy stalkers. Then later on phone jobs I got asked out every once in a while and used the same excuse.

            1. Stranger than fiction*

              Oh wait, I did actually end up in a four year relationship that had been a customer and he ended up being a creep with major control issues, but that could have happened no matter where we had met. (Funny I mentally blocked that)

        2. Sarahnova*

          OP: I think most people can tell when there is some genuine interest going on.

          Hahahahahahahahahahahahahah. If only.

          -signed, every woman who has ever been accused of “leading a man on” for smiling at him, listening to him, or not appearing immediately repulsed by him.

          In all seriousness, young and youngish women in customer-service jobs are frequently dealing with a more-0r-less daily barrage of men who interpret “smiled at me and was polite” as “wants me”, and it can be exhausting and, yes, scary, since a significant fraction of men don’t take a polite “no thanks” well. I would go so far as to say that if you, man, think an employee, woman, likes you, to think deeply about how good your judgement in this area typically is before you ask her out in said low-key, low-pressure way.

          1. neverjaunty*

            Yes, this. And “I am interested in this person” is not exactly placing the Objective Viewpoint Ray on high beams in illuminating whether the nice person at the store is, in fact, genuinely interested.

            If you’re going to do this, the leaving your number AND THEN LEAVING, with the expectation of not returning to that business, is the least awful approach.

          2. And we danced from the ocean*

            … young and youngish women in customer-service jobs are frequently dealing with a more-0r-less daily barrage of men who interpret “smiled at me and was polite” as “wants me” …

            I wonder if anyone has ever gathered real data on this? It would be fascinating. Like, just reading the ‘net, it’s easy to get the impression that a good 80% of men are creepsters. It may be true, but I strongly suspect it’s not, and it’s a consequence of anecdotal data, how a creepy experience is much more memorable than a dull ‘normal’ day at work, and so on.

            1. Uyulala*

              It’s a numbers thing. If only 1% of the population are creeps and you have 200 people come into your store each day, that means that you need to deal with 2 creeps every single day.

              1. Sparky*

                And each creep is going to make contact with every victim that he possibly can, perhaps more than once. And “I have a boyfriend” doesn’t even slow down most of these guys.

                1. TootsNYC*

                  Yep–true creeps are spreading it around as much as they can. So they’ll make a HUGE impact, far more of an impact than the 600 perfectly reasonable men who went through the store that day.

                2. SevenSixOne*

                  Something like the Pareto Principle is definitely at play here– 80% of creepy, inappropriate behavior comes from 20% of the population.

            2. Sarahnova*

              It’s not so much that it’s “every man” or even most men as that it’s frequent enough, and WHICH man it is is totally unpredictable. A perfectly well-kempt, apparently reasonable, gainfully employed and up-till-this-point-calm-and-polite man can and will suddenly turn into an epithet-hurling, personal-space-invading, boundary-crossing scary jerk when the words “thanks, but no” are uttered. As a consequence, we have to have our radar on all the time, because we have no idea which are the jerks/creeps/violent sexual offenders until they get jerky/creepy/assault us. Google “Schrodinger’s rapist” if you want the full scoop.

        3. Ellie H.*

          I couldn’t agree more. I do not understand why being asked on a date (or simply learning that someone is attracted to you) is apparently now widely considered a traumatizing experience to be protected against at all times.

          1. Jennifer*

            Because at least some of us have gotten really, really scary reactions from men when we turned them down. This is extra worse when you’re a captive audience who can’t get away from them at work, and it’s why a lot of us would recommend not asking at all or proceeding with extreme caution.

            That said, if the OP is a woman interested in a man, her odds of him going psychotic on her are a lot lower than in the reverse, so she might have better luck.

            1. Sarah*

              Yes, and if you work in retail and your boss is an arsehole who thinks making a customer unhappy is a fireable offence – or just if the one who’s asking you out won’t stop bugging you at work, etc etc

        4. INTP*

          Studies show that men are not actually able, on average, to pick up on disinterest, if they’re interested in the person. I’m not sure about women.

            1. ancolie*

              Studies have actually found that men are just as capable as women at understanding nonverbal communication/”soft no”s. The difference is that many* men will IGNORE those signals because what they want is more important to them than respecting the other’s wishes. Or, to put it more pithily, as this linked post full of citations says in its title, Mythcommunication: It’s Not That They Don’t Understand, They Just Don’t Like The Answer
              https://yesmeansyesblog.wordpress.com/2011/03/21/mythcommunication-its-not-that-they-dont-understand-they-just-dont-like-the-answer/

              * #notallmenobviously, note the qualifier.

        5. Daisydot*

          Hi, OP here. Thanks very much for your thoughtful comment. I was actually a little traumatized by Alison’s advice (although I do really appreciate that she replied and has provided a forum for others to respond) and the first couple of comments (this was much earlier today-I was shocked to see all of the responses that are here now and have just started going through them), so I stopped by a female friend’s shop today to ask her advice. (I’m female, btw, and the employee in question is male. I worked for years in retail when I was younger and fended off unwanted requests for dates successfully and without any kind of emotional scarring.). I was able to give my friend additional details and she said that the employee sounds nervous and that I should just give him a note, and that in fact, a customer of her own has been leaving notes for awhile and they are now dating. My main concern was that I didn’t want to put this person in an uncomfortable position or jeopardize his job, and what you’ve recommended sounds like it would work so thanks very much for the advice :)

    2. Lily in NYC*

      I dated someone for 5 years – he was a customer who asked me out. I got hit on constantly at this job and hated it, but this guy was different and I always looked forward to seeing him. So I wouldn’t just give a blanket “no” as advice. However, I would go about this very, very carefully and only do it if you are more than reasonably sure that he feels the same way.

      1. Wakeen's Teapots Ltd.*

        Nothing ventured, nothing gained!

        Unless we want to rely on eHarmony to produce the next generation, you have to take advantage of opportunities that present in the real world.

        What the worst that could happen from politely and not creepily seeing what happens next from this real world connection?

        1. Kathryn T.*

          The employee feels panicked and caught between a rock and a hard place, like he may not be able to turn the customer down without pulling down the wrath of management, and what had been a friendly encounter now turns into a recurring nauseating anxiety.

          1. Wakeen's Teapots Ltd.*

            That would be some might serious dating phobia to have that reaction from a casual reach out, he’d be quite the outlier with that level of panic.

            We’re not talking about sexual harassment, for heavens sake, it’s coffee (or actually, better causal ideas downstream).

            This is how normal people meet, during the course of a normal day.

            1. Kathryn T.*

              It’s not *dating* phobia per se — it’s management phobia. There are definitely some completely unreasonable managers out there, particularly in retail.

              But regardless, you asked “what’s the worst that could happen,” not “what’s the normal thing that is most likely to happen.” And, well, there you go, that’s probably the worst that could happen.

              1. I'm a Little Teapot*

                When I worked retail, a man who grabbed me from behind when I was alone in the store and I told him to get his hands off me. Later, on hearing about it, my nasty coworker who was a demoted ex-manager told me that I “shouldn’t have been rude to a customer.” So I can definitely imagine a manager who would expect someone in a customer service position to say yes to keep the customer.

                I’m not saying you should absolutely never do it, but if you do, make sure it’s very clear that “no” is a completely acceptable answer and that the person’s manager and coworkers will never know about it if the person declines.

        2. neverjaunty*

          The worst that could happen to whom? The employee being hit on?

          Also, regardless of the merits of OP asking/not asking, can we PLEASE roundfile the whole “but how else is the species supposed to continue” fallacy, which, bluntly, gets trotted out in defense of everything from workplace harassment to stalking. Because to answer the question, there are plenty of opportunities to meet people in the real world that don’t rely on one person having to be nice to the other for the sake of their job.

          1. Wakeen's Teapots Ltd.*

            You can round file it if you like but I’ll do as I please.

            I’ll remain concerned that if a trend of two people people meeting public and getting to know each other has become zomg dangerous and exploitative, and don’t know how ya’ll are going to make it through.

            Men and women (and women and women, and men and men) have made simple personal connections this way since the beginning of time. It’s normal. (Well, I guess it was scandalous when marriages were arranged so okay, normal since women got agency.)

            1. neverjaunty*

              I really don’t understand the snark here, much less the ‘do as I please’ – nobody was threatening you with a restraining order.

              Many, many people have posted here about their experiences working in customer service positions, which require them to be pleasant and nice to customers as part of their paycheck, and how unpleasant and difficult it is to negotiate romantic interest from customers when that power imbalance exists (and particularly when there are people who rely on or even enjoy that power imbalance). Responding to that with flip remarks about how will the species survive or how it’s always been this way or how people who object really need to deal, frankly, comes across as wildly and deliberately obtuse – which, again, is very out of character for you.

            2. LibbyG*

              But this isn’t “two people meeting in public.” It’s public for the customer but a workplace for the employee. I agree with Alison: it’s not “no no no never never never” but one must be exquisitely aware of the context, which means an “almost never” thing.

            3. LPBB*

              The thing is that you seem to be looking at this as though these two people are meeting as equals, but they’re not. There is a certain expectation put on the retail worker to always be polite, to be friendly, and to be helpful. Personally, I’ve never really liked turning people down in any setting, probably because of my conditioning as a woman in this society, and it just gets weirder and more awkward when I’m in customer service/don’t upset the customer mode, even if that customer is normal and not some creepazoid that rings every alarm bell of every female on staff.

              No one is saying that you can’t meet people in public places or even workplaces. I met my husband in a bar; I met my previous boyfriend at our mutual workplace. I know people who have met because they ride the same train to work every day or they’ve attended the same sporting event. What people are saying, is to be aware of the power differential, be aware that the person you are asking out may be in a situation where their behavior is constrained, be considerate of the other person’s situation, don’t take advantage.

              I’d also like to point out that for all of your talk about women having agency and being liberated, that you’re not actually listening to all of the women who have posted here saying that they do not enjoy being hit on/creeped on/asked out by customers at their place of work and that they just want to do their job without feeling like a Playboy bunny. Part of having agency and being liberated is being able to say, “Hell, no! I’m sick of this and I don’t have to take it!” One reason why you hear more and more complaints from women in retail is precisely because they are empowered, not because, as you seem to be implying, that we are all a bunch of fragile, frigid, special snowflakes who want to criminalize all interactions between men and women.

              1. ancolie*

                “Part of having agency and being liberated is being able to say, “Hell, no! I’m sick of this and I don’t have to take it!” One reason why you hear more and more complaints from women in retail is precisely because they are empowered, not because, as you seem to be implying, that we are all a bunch of fragile, frigid, special snowflakes who want to criminalize all interactions between men and women.”

                QFT. Absolutely perfectly put.

        3. Valar M.*

          An online dating website is the real world. You’re just engaging through a different means of communication rather than face to face.

        4. Sparky*

          “Unless we want to rely on eHarmony to produce the next generation, you have to take advantage of opportunities that present in the real world.”

          Not eHarmony, they discriminate against gays and lesbians.

    3. Chris80*

      Agreed. As someone who has worked in customer service for a long time, I can tell you that it will make many customer service reps very uncomfortable. I put up with flirting from customers at my job all the time because I’m in a position where I’m being paid to be nice and don’t feel like I can shut it down like I would outside of work.

      That said – I think that the fact that you know it could be awkward speaks well of you, OP. It shows a level of awareness that not everyone seems to possess in these situations.

    4. Anne*

      This could go either way! I worked in a restaurant and customers hit on me often but the man I am now married to, for 38 years (!) was a customer that I wanted to hit on me! He didn’t, but then I saw him one night at a club and I approached him and the rest is history! You really have to go with your gut, I think.

    5. Mia*

      !!!!

      This.

      As someone who works in customer service and is literally paid to be nice to you, please don’t do it. I have a boyfriend. It’s awkward. I’m not interested. And I just want to get my paycheck and go home.

      1. Stranger than fiction*

        Ok but, not so single you out Mia, but how is turning someone down politely not being nice to the customer?

        1. Journalist Wife*

          Well, we have to also figure out if the customer service involves tipping or not. I used to wait tables when I was young, and a lot of times guys (and horribly old men, too!) would come in, sit in your section, chat you up, and if you flirted back they tipped you well but if you didn’t, or if you said, “I have a boyfriend,” you got no tip. I’m not saying these were nice guys who decided not to tip if you didn’t take the bait, but I couldn’t choose who sat in my section — I just had to hope they were going to tip me. I got asked for my phone number all of the time. If I thought I was going to get tipped regardless (i.e., they were with a group and split checks, etc.) I declined. If I didn’t think i would get tipped if I turned them down, I gave them a fake phone number and then smiled when they left me a whopping tip behind. Although once I did meet a very nice young man who sneaked back in after his party had left to ask me for my phone number but promised that he would never sit in my section again if that embarrassed me or made me uncomfortable. He is the only person who ever scored my “real” phone number, and I wasn’t a bit sorry. We ended up going separate ways in life, but he was a total gentleman and excellent +1 while it did last, and I still hold him in high regard years later.

        2. Anna_L*

          Ugh, do you know how most men respond to being turned down? Trust me on this, it’s not good..

          1. Lily in NYC*

            Most? I don’t think most men handle being turned down poorly. Some do. Not most.

            1. INTP*

              When you are in customer service dealing with many people every shift, and are attractive enough for a significant number to be attracted to you, even 5% of men being jerks is enough to result in negative consequences on a regular basis. And the employee has to assume you might be one of those jerks in choosing how to respond to you if she doesn’t want to lose her tip or get a complaint. So no matter how nice you think you are, you could reasonably make a flirtee feel uncomfortable and trapped into responding to you.

        3. katamia*

          You never know how someone’s going to handle rejection if you don’t know them well (and even sometimes if you do). It’s safer to assume, fairly or not, that they will react poorly and plan accordingly, especially when it could be your job on the line–they could complain about you to the manager or yell at you and even turn out to be a creepy stalker.

      2. LPBB*

        A lot of people get off on exploiting the power imbalance between customer and customer service rep. It is not out of the realm of possibility that someone might make a complaint, factual or otherwise, about a retail worker who turned him/her down. A lot of managers will take the word of the customer over their employee, so it is not out the realm of possibility to be written up for that complaint. It is understandable how someone who works for an unreasonable manager or one who routinely sides with the customer could be concerned about what will happen when they turn that customer down.

  2. Former Diet Coke Addict*

    Look, retail employees get hit on day in and day out. Please don’t. Please. It’s incredibly uncomfortable to be hit on by a customer who you can’t say what you feel to, and there’s a really uncomfortably dynamic.

    It would be ok if you ran into an employee somewhere else organically. Please don’t hit on retail employees. People always think they’ll be the exception to this, but….ugh. Please refrain.

    1. fposte*

      Could be I’m old-fashioned, but I think asking somebody out can be different than hitting on somebody.

      “I really enjoy talking to you here and I’ve thought it might be nice to do it outside of work sometime. If you’d like to try that, here’s my number; otherwise, I’m happy just to encounter you as an awesome barista/whatever.”

      Important: you give your number and don’t ask for his number, and you do it on paper so that you don’t need to text to his number or handle his phone to input anything. And then you never, ever speak of it again.

      1. OriginalYup*

        I see what you’re getting at, but my experience in retail and food service was that everybody doing the latter still thinks they’re doing the former.

        OP — think twice, thrice, four times before you do this. He’s at work. If you’re 99.9% certain about letting him know you’re interested, then fposte’s wording is the way to go. And the never mentioning it again is mandatory.

        1. phillist*

          “I see what you’re getting at, but my experience in retail and food service was that everybody doing the latter still thinks they’re doing the former.”

          +1000. If you ever want a tutorial in why this is a Very Bad Idea, go ahead and read the Craigslist “Missed Encounters” section, particularly the men-for-women. These guys write Odes of Undying Love and Devotion to the people who make their coffee every morning, and generally feel like it’s reciprocated because they “smile at me every time I come in”.

          I may have spent several hours of my life yelling, “YES OF COURSE SHE DOES THAT IS HER JOB” at my computer.

          1. some1*

            Slightly OT but those ads were my free entertainment when I was unemployed. One was reeeally bad: the guy saw this woman at Target (they were both customers) and saw her in the parking lot and asked if she needed a ride because it didn’t look like she was walking to her car. She declined, and he drove by her as she was walking to the bus stop and rolled down his window and asked her again if she wanted a ride. She again said no. She was probably scared shitless.

          2. Roly Poly Little Bat Faced Girl*

            phillist — this is what immediately sprung to mind to me when I read this question. The Craigslist “Missed Connectios” where I live seem to have a lot of men who want to connect with the women who cut their hair, probably because it’s a longer encounter and there is more chit chat. The ones that I find the creepiest start out with, “I know I’m probably too old for you…”
            And you’re right. It’s her job to make connections with her customers and, you know, be nice.

            1. Valar M.*

              This x a million. I got hit on by so many men when I was 16ish that could have been my father. One of the worst parts of retail was being trapped into conversations with these men over and over and not being able to walk away. I had to over-analyze every word that came out of my mouth so as not to sound too friendly or encouraging.

            2. KH*

              My dear Internet god, those posters on Craigslist are pathetic. My hope for the human race has just fallen by another notch. Truly cringeworthy, I had to stop after 5 minutes.

          3. GenericGen*

            Oh, my bleeding eyes. I didn’t know there was a section in Craigslist like that. I just checked it for my area, and, sure enough – “I delivered your pizza last night; you were in a swimsuit”. And in the body of the post – “This is what fantasies are made of; the pizza guy and the sexy woman”. Oh, sure. It’s HER fantasy. O_o Yeah, no.

      2. Jenn*

        I agree that asking someone out can be different than hitting on someone, but for me as a woman in a publicly funded service role (library type work) I’m pretty sick of being seen as on display and treated as a piece of meat at a buffet that people can ponder, look at, ask questions too, and ask out. I just want to do my job and part of that job is being nice to people and making sure they are enjoying our services. I don’t want to be reminded on a regular basis that people are thinking of me in a sexual way while I’m working.

        1. saby*

          Is it just me, or are libraries worse than other environments? I guess the “sexy librarian” thing does not help in that respect either :(((

          At one library where I worked, we were actually told to stop wearing our nametags because there was so much of this.

          1. HR Generalist*

            I used to work at a library too and we were always told not to give out our full names and to be vigilant of patrons. We were students and had a few regulars known to follow us around the stacks while we’re working (one would mutter under his breath the whole time, we thought it might’ve been poetry… ugh…).

          2. A*

            Not a library, but I’ve worked all over the food service and retail spectrum, including a major event stadium regularly serving 60,000 drunken bros in party mode, and the most I ever got hit on was the 6 months I worked at a Barnes and Noble.

            There really does seem to be something about the “librarian/bookstore girl” stereotype, and the kind of men that go for that, that makes things creepy.

            1. Rebecca Too*

              I work at Barnes and Noble, and I am shocked at how often I get hit on/asked out. “Let’s have coffee when you get off work” seems to be the go-to line. Anyway, I’ve taken to wearing a gold band on my ring finger to discourage that behavior, but men don’t seem to notice. Or care. Which then bums me out further….

            2. Anon.*

              Video games. I (female, red-haired) worked in video game retail for a while. I got hit on more in 6 or 8 months there than I have in the rest of my life put together.

          3. LPBB*

            When I worked in the bookstore I stopped wearing my nametag (with the blessing of my awesome manager) entirely, because of all of the unwanted attention.

          4. Io*

            Secretarial positions suck for this, too — for what I’m sure are the same reasons. It’s very frustrating.

            1. anonanonanon*

              Agreed. I dealt with this just as much in a secretarial position as I did in retail. It’s just as uncomfortable and frustrating.

              1. KH*

                Let me apologize in advance for all the guys out there who do this. To an extent, we can’t help it. It’s how our brains are wired up. But those of us who are normal don’t actually do anything. Apologies on behalf of the male half of the human race.

          5. pony tailed wonder*

            I work in a library so I don’t have any other environment to compare it to but there are students who do not understand boundaries and do not understand the difference between friendly customer service and flirting.

            *Actually, I was a lifeguard in another life. I did get hit on a lot way back then but it was always little boys who wanted me to come over and play and have milk and cookies later because their mom just made the best, etc.

        2. A*

          I’m a public librarian, married to a patron. We flirted for (probably 5) months and I finally asked him out one day. That was 8 years ago. Only guy I’ve ever asked out!

          I think the difference was that while he complimented me plenty, it was never about my appearance or anything physical. So it didn’t seem as creepy as when patrons would say “you have a really beautiful smile.” Which I do, but don’t want to hear from a stranger.

      3. eee*

        Disclaimer: I have never worked in retail, so I’ve never had this experience. however, my friend (who works in retail) asked out a barista who she had a crush on. She’d been going to the coffee shop for several months, and he was really friendly every time they talked, complimenting her on safe topics like her manicure, etc. She did fret for quite a bit over whether she was misreading general “customer-facing friendliness” for flirting, or whether he really was interested in her, but only platonically. She wound up finally, after months, during one of their rounds of banter, writing down her number and giving it to him and saying something like if he wanted to get to know her outside the coffee shop, he could text her, but if he didn’t that was fine too. He texted her later that night and now they’ve been dating for like three months!
        factors in her favor: -she is a very nice, polite person who would definitely have apologized and avoided ever going to that coffee shop again if he seemed offended or creeped out
        -while she wasn’t ever really convinced that he was flirting with her, everyone else was
        -he remembered her each time, knew and remembered details about her (where she worked, what her schedule was like, her name), etc.

        1. RMRIC0*

          It’s probably also one of those things where it’s socially more acceptable for a lady to do it than a gentleman.

          1. eee*

            true–also as a guy he would probably feel less threatened if the attention was unwanted.

            1. Hotstreak*

              Absolutely. I am a fairly attractive, personable guy and have been asked out by several customers over the years, and it’s never been a problem. The women always gave me their number and let it be known they “weren’t doing anything on Thursday” or whatever. This is NOTHING like the experience of attractive (or even unattractive) women I worked with. They get stared at & aggressively flirted with on a regular basis.

            2. Anonna Miss*

              Giving someone your phone number and saying that it’s cool if they text you (AND that it’s cool if they don’t) probably helps a lot here, or would help in general. You’re not leaping from someone making your latte to a dinner date, AND you’re not forcing them to respond right away, you know, when they’re working…

      4. Turanga Leela*

        I came here to say exactly what fposte said. Express low-key interest in seeing the person outside of work, give your card/number, and make it clear through your words and actions that you can happily take no for an answer.

      5. 42*

        OMG yes. I can’t throw enough yesses at this reply, fposte.

        Casual, ‘here’s my number’, and then leave it. That’s how it’s been done forfreakingever. Do it OP. Answer’s always gonna be ‘no’ if you don’t ask. Too much overthinking going on here.

      6. Stranger than fiction*

        I must be old fashioned too, how in the heck are people supposed to meet these days if you don’t want to do so at bars or online?
        But fr what a lot of people are saying here, has the world just gotten that much more creepy?
        That’s sad.

        1. Revolver Rani*

          “how in the heck are people supposed to meet these days if you don’t want to do so at bars or online?”
          Book club. Community choir or orchestra. Religious group. Toastmasters chapter. Martial arts class. Adult education class. Mutual friend. Bookstore or coffee shop or any number of other public places in which neither of them is at work doing his or her job at the time of the encounter.

          Personally I think the “here’s my number if you would like to talk when you are not at work” approach sounds okay, although I totally understand the problem here. Enough folks in customer-service positions have testified on that thread that they get unwanted solicitations so often that even if you are the nice person who means really well, you might still be a REALLY annoying straw on that camel’s back.

          But this objection, that there is no other way to meet people besides asking them out when they are WORKING, is pretty silly.

          “has the world just gotten that much more creepy?”
          The world is as creepy as it’s always been, but women have been learning to push back against some of the crap that society heaps on them as a punishment for merely existing and being female.

        2. Jennifer*

          The world has always been creepy, you just weren’t aware of it.

          Honestly, I think you get lucky or you don’t on meeting people. I’d rather meet people doing things I’m interested in or through other friends.

          1. Kelly L.*

            +1

            I don’t think I’ve actually ever met a rando in public and ended up dating them for more than one date (and very, very few of those). All of my long term relationships have come from mutual friends or activity groups.

      7. INTP*

        In an ideal world, a polite request for a date wouldn’t be totally inappropriate. But it’s not an ideal world and sexual entitlement doesn’t always come in obvious, high pressure, sexually explicit packages. An employee could reasonably feel just as trapped into responding favorably to the polite request for a coffee date as a skeezy come on.

        Basically, it’s not the question that is the problem but the power dynamics and concern for what might happen if you reject them given those power dynamics. Asking nicely doesn’t erase that.

    2. SevenSixOne*

      Two things OP should consider:

      1. Many people really don’t know how to interact with someone of the opposite sex in a way that’s not flirtatious and/or interpret any positive interaction with the opposite sex as flirtation (I’m a lot better about this now than I was in my teens and twenties, but I still catch myself thinking/acting like this sometimes)

      2. At all the boring customer service jobs I’ve ever had, my co-workers and I flirted recreationally with customers and each other. We didn’t mean anything by it, it was just a way to break up the tedium.

      OP, are you sure neither of these things area happening here?

      1. Wakeen's Teapots Ltd.*

        She can’t be sure but either he wants a cup of coffee with her or he doesn’t. It seems pointless to overthink when the answer is either yes or no.

        1. mskyle*

          I think there’s a power differential between the customer and the employee that you’re missing here. It’s not as dramatic as a manager asking out his employee, but in many retail environments the customer *absolutely* has power over the employee. Also, the OP doesn’t need to “overthink”: the answer is almost certainly “no.” He’s probably being nice to the OP because being nice to customers is part of his job. If he’s “staring” at the OP it’s more likely because he thinks the OP is a potential shoplifter than because he’s romantically interested.

          I think if the OP really, really wants to follow up on this guy, the way to do it is by very gradually escalating and paying a lot of attention to his responses.

      2. A*

        There’s also the fact that we don’t know the OP’s gender, and we don’t know if this is opposite sex flirtation. I actually thought the OP might be a man.

        Which really just makes things more complicated, since there’s no way for sure to know his crush’s sexual orientation (something heterosexual would-be workplace-suitors should also keep in mind) and there’s sadly more potential for the reaction to be negative if he’s wrong.

        1. Ad Astra*

          My guess is that the OP is a man, simply because men (of all orientations) are more likely to hit on service employees than women are. It’s a social conditioning thing.

        2. Yes*

          I was happy someone mentioned that. When I worked retail, I got hit on a few times by male customers. I date women. The whole thing was awkward (dude who are you and why are you asking me out after literally 1 minute of interaction?) with a side of awkward (sorry, I play for team rainbow, but good luck to you). At the time, it didn’t seem safe to tell a random stranger my sexual orientation- especially when my co-workers didn’t even know (long story, that..)

          I usually just tried to be extra nice and funny about it without bringing in the orientation thing, then went on with the rest of my day. (Only bc in my case they were thankfully never true creepers). I think the only thing saving me from flirting being a daily occurrence where I was assigned was that our typical customers were older, often married, women. I also had freedom to roam, which, of course, a barista doesn’t have. It was more of a problem dealing with the guys that worked nearby and shoppers in public areas.

          With same-sex flirting, I feel like it’s a zillion times harder. It’s realllllly hard to know someone’s sexual orientation when discussing a cinnamon bun or what have you. But regardless of where the pendulum swings, they are stuck behind that counter, so there’s a power issue. There is also the fact that their job hinges on them being nice to everyone- also a power issue. So, for me, I’d play it extra-super-cautious and wait for the big neon sign and the person to ask me. But, you know, it’s such a personal thing, asking someone out. Just try not to come off like a creeper if you do ask, and really try to absorb the advice the other commenters have provided.

      3. Daisydot*

        Well, he’s not at all flirtacious and if he were I doubt that I’d take him seriously. He just seems interested.

  3. Bri*

    As a former retail manager I am ok with my employees going on dates with customers as long as the customer is the one who did the asking. It’s possible that he is burning with desire for you but would get in serious trouble if he asked you out on a date. A lot of males who work in retail treat their job like the Bachelor and it’s extremely frowned on. I think the best thing to do is go in right before close and mention something like “I’ve been craving cheese fries from place super nearby I was going to go with my friend but they bailed. If you like cheese fries maybe you should stop by”

    1. fposte*

      Oh, I didn’t even think about the “maybe you should stop by,” and that’s great. Another good thought in that direction is include them in a party invite–“Hey, I’m having some people over on Saturday–come on by.”

      1. ineloquent*

        That’s exactly how I’d do it. Make an effort to get to know your crush in a non-work context before asking him out.

      2. jmkenrick*

        I’m in the camp that thinks it’s OK to politely ask someone out even if they’re working, but obviously many other differ.

        The ‘I’m having a party, stop by if you’d like’ does seem like a good possible compromise…I think it’s because that’s phrasing the request in such a way that the burden isn’t on the employee to say no.

        Another way might be something along the lines of:” “It’s always nice to chat with you [name.] If you ever finish early and want to join me for a cup of coffee, let me know.” – Something that puts the ball in the employee’s court without putting pressure for them to come up with a polite on-the-spot rejection.

      3. fluffy*

        Women should never go to an unfamiliar man’s private address. Meet a friendly stranger in a very public, preferably bright lit space and, preferably surrounded by old friends and family.

        Don’t arrive at a house and find there are no other guests.

        1. Wakeen's Teapots Ltd.*

          People should use common sense caution. Women aren’t delicate flowers and men, as a gender whole, aren’t big scary monsters.

          An intelligent woman shouldn’t have a problem meeting a prescreened “stranger” in a public place without having to take friends a family on the date. We go out in public with strangers all the time after all.

          1. T*

            As a guy, I don’t worry about the woman attacking me or anything but I do think about getting robbed by someone else hiding at her place. You typically only hear those kind of stories with hookers and johns (because you’re not going to the cops to report a pimp robbing you) but I assume it happens to regular people too.

          2. fposte*

            Right, this proscription would mean nobody in college would ever go to a party.

            And it’s fine to say “Cool, could I bring my friend Xanthippe?” and then do so, check the address and person out beforehand, and bail at any time.

          3. cardiganed librarian*

            Seriously. If you can’t meet a stranger in a public coffee shop on your own, how on earth is internet dating supposed to work?

            1. Wakeen's Teapots Ltd.*

              It’s all too “a single woman should be accompanied at all times when out in public” 191o for me.

          4. sam*

            it’s funny (not funny “ha ha”). When I was backpacking through europe as a solo woman traveler back at the age of 22, I never had an issue myself, but I encountered, in youth hostels, several men who had been mugged/robbed/etc., including one guy who had actually gone out drinking with locals and woke up the next morning in the hospital to discover that he had been drugged and all of his documentation and money was gone.

            I’m not saying that women never have trouble, because of course they do, but every one of the incidents that the men described were situations where all of the women who were in the conversation were basically “what the hell were you thinking going somewhere alone with a stranger/letting a stranger get that physically close to you?”

            the flipside of male privilege – men get to generally live their lives without an underlying fear of being raped…but once in a while that fear comes in real handy.

          5. Ad Astra*

            Eh, I would absolutely insist on meeting someone where there are people around, even if they’re neutral parties. And I would tell a couple of friends where I was going and who I was with. And I’d probably be sure to check in on Swarm so there’d be a record of it.

            I would not go to a private residence alone if I hadn’t hung out with someone before. It’s not about all men being big scary monsters, it’s about trying to avoid situations that put you at a disadvantage in case someone does turn out to be a monster.

            1. Wakeen's Teapots Ltd.*

              Sure. That’s a good practice for people. I object to singling out women.

              I came of age during a time where it was new and shocking for women to take planes, trains and automobiles on their own. I remember the first time I took a Business Trip. Across the Country. A Woman, traveling alone!!!

              Just as fraking capable of taking care of myself as any man ,thankyouverymuch.

              There’s a lot of baggage (no pun intended) with singling out Women For Special Protection.

              1. Hotstreak*

                That’s great in theory & hopefully one day we get there as a society, but the cold hard fact is that women are so much more likely than men to be assaulted or coerced on a date.

        2. anonanonanon*

          +infinity

          I would be so creeped out if someone I was unfamiliar with asked me to “stop by” their home, even if they phrased it as a party invite. If I didn’t know them outside of the customer-employee interaction, there’s no way in hell I’d go to a private address.

      4. And we danced from the ocean*

        I’m going to respectfully disagree. Meeting someone at a party (or going to a movie, while we’re on the topic) are not especially good “first dates” when you’re attempting to get to know someone better. Some people can make it work, sometimes. But many parties are crowded and noisy and everyone is running about mingling. And movies are basically sitting in the dark next to someone for 90 minutes in an environment that does not favor socializing. *shrug* again, I’m sure there are some people who are great at movie and party first dates. But I think there are easier first dates.

      5. TootsNYC*

        I wouldn’t necessarily invite someone I’d met in this compartmentalized way to my home.

        But I was going to come and suggest something like, “Are you going to the ZYX event? It would be fun to run into you there.”
        Or cheese fries because my friend bailed.
        Or some other thing where you set out an opportunity to see you, an easy one, and see if he takes it. If you’re friendly and encouraging about it, welcoming, then his response will tell you. If he says, “Oh, I have to get home,” maybe he’s not so interested. If he say, “Oh, rats! That would be fun. But my dog is waiting for me, and I really can’t hang around. Maybe we could get cheese fries on another day,” then you know.

        Do the “invite to something neutral,” and see what the reaction is.

        Or, just be a little more obvious about YOUR flirting; hang there beside him just to talk to him, and then watch is body language; is he glad of it, or does he start to get antsy or pull away after a polite interval.

        Test more. Flirt more. Until you have a stronger feeling.

    2. Language Lover*

      This is exactly what I was coming here to post.

      Or if you know you have a shared interest from the conversations you’ve had while in the store…like you both do yoga, you could mention that there’s this great little yoga class down by the lake that you go to and maybe he should stop by.

      Something that lets him know where you’ll be if he ever wanted to bump into you outside of a work environment.

    4. Ad Astra*

      “Maybe you should stop by” is perfect because simply not showing up is a lot easier than rejecting someone outright. The customer may never know if the employee wasn’t interested or just couldn’t make it, which can be tough, but it also means the customer can’t take it personally.

    5. INTP*

      I like the low pressure approach. I still think it could make women feel trapped into flirting back lest they be seen as rude or ungrateful but it’s better than flat out asking. I’d go even lower than your suggestion though, which still sounds like a clear request for a date. Maybe mention a place nearby that you frequent, like the coffe shop you visit before work or your gym or the bar you sometimes have happy hour with coworkers at. If they’re burning with desire, they’ll run into you.

    6. Daisydot*

      Thanks for your perspective on this Bri because this is something that I was really wondering about. And thanks for the suggestion for a no-pressure meet-up, that’s a super idea!

  4. gsa*

    Since the OP is the customer, if read it correctly, the OP should ask the question.

    Some how it’s easy in my mind…

    Hey do you want to 123?

    We should xyz some time.

    Nothing gained, nothing lost.

    My base presumption is the OP is generally comfortably asking a person “out”.

    1. WorkingMom*

      I have to admit – I had NO idea that this was a *thing* with retail employees. If I were single and shopping and met an individual I’d like to ask out – I would have. I wouldn’t have even thought twice about it… it honestly never would have occurred to me that it might cause issues for the employee, or that this was a common issue for retail employees to deal with! No real point to this expect to share that I have now been enlightened :)

    2. Daisydot*

      Thanks gsa, I’m actually not really comfortable asking someone out, and then there is the whole customer/employee dynamic, but it sounds like I’m going to have to be the one to make a move so thanks for the reinforcement!

      1. gsa*

        Ms. Dot,

        I have been investigating my ability to search for past posts. I was looking for posts/comments I made and making sure I not did left some hanging…

        Did you make that move?

        gsa

  5. Charlotte Collins*

    I agree – don’t do it. It sounds like he’s just good at being a retail employee. They are paid to be nice and helpful and to show up where you’re shopping if they think you might need help. (Then again, he might also think you’re a shoplifter, for all I know… But probably not.)

    If you run into him somewhere else, that would be fine, though – if you got the signals that it would be welcome.

  6. Stella*

    Hmm I once gave my phone number to someone who worked the counter at a restaurant after seeing them there a few times. Nothing high pressure, just “hey call me if you want to get coffee.” We hung out a few times, then both moved away from the area but we’re still friendly now. I think as long as it’s very very casual (coffee date, maybe a museum) and said with a cheerful smile (and maybe a “no pressure, I don’t want to put you on the spot” thrown in there) there’s no real harm. And as long as you are willing to hear them say no (and you are not a crazy person) then there is not a lot to lose.

    There are probably a lot of gender dynamics at play too (I’m a female, I asked out a male) – if the roles were reversed it may feel more awkward.

    1. Daisydot*

      OP here, I’m female and not crazy :). Thanks for sharing your positive experience!

  7. EJ*

    No! I worked at a coffee shop for a few years… so awkward when people would hit on me. It’s like, I’m working. Can I just work in peace without having to hide from horny men? It’s not flattering, it makes me cringe. I get enough catcalls on the streets. Please have some respect and let me have my JOB as a “safe space”!

      1. Panda Bandit*

        You’re missing the point. She said she’s there to work, not to get hit on or asked out.

      2. INTP*

        Does it really matter if the guy is asking her out because he’s acutely horny or just anticipates being horny? Unless he’s asexual or asking her out for pointedly platonic motivations with zero thought to the possibility of a romantic or sexual relationship ever developing, it’s basically the same thing. An awkward situation she is placed in repeatedly by men, through no doing of her own and with no way to prevent it, due to their sex drives.

  8. Squirrel*

    I think people should recognize the difference between hitting on someone (e.g. a silly or gross pickup line, or outright propositioning) and a simple “asking out” (e.g. “Hey, would you like to grab coffee sometime?”). I too worked retail and was both hit on and asked out. The guys who hit on me were really gross and it was quite a turn off. But the guys who were polite and made a no pressure suggestion to grab coffee or see a movie sometime or whatever, were not doing anything wrong. I let them all down gently, the ones who were grossed I told my manager about, and the ones who were polite [key point] were cool with me afterward and there was no awkwardness between us [key point]. There’s nothing wrong with letting someone know you’re interested as long as it is no-pressure, you don’t treat them differently afterward, and you are OK with being shot down. I think people are going a little overboard with the sexual objectification and harassment-type comments. I’m sure the OP isn’t looking to treat the worker like a piece of meat for their amusement. Let’s give them the benefit of the doubt here.

    1. jmkenrick*

      I think this is well said and I agree with you.

      I worked retail all through college and I never really had anyone ask me out (apparently I’m the exception based on these comments?) But I did once have someone hit on me, and to me the difference is generally pretty clear. Hitting on generally is either straight-up propositioning or coming in sideways.

      Asking is out is just “Let me know if you’d like to grab coffee sometime.” And yes – getting asked out does often make me feel uncomfortable if I’m not interested. Of course. I don’t feel very comfortable or happy rejecting people. But I don’t think that means that they shouldn’t do it. Frankly, lots of social interactions make me feel a little weird or uncomfortable, but they’re totally normal and acceptable interactions nonetheless, and I don’t think my discomfort always reflects negatively on the people doing the initiating.

      1. OriginalYup*

        But see how you’ve mentally filed this under “social interactions”? That’s the point — for the worker, it’s a business interaction. There’s a lot of faux-socializing in retail that’s meant to put the customer at ease and convey a general politeness expected in dealing with human beings (“Hi, how are you today?”). But it’s still a business interaction. And a lot of the general public gets that mixed up with actual proper social interactions, where both parties can leave the conversation any time they want.

        I don’t think it’s a horrendous crime to ask someone out, I just remember wishing (as a former waitress) that people would just let me bring them their food instead of assuming we’re friends now because we’ve been interacting for 8 minutes in my place of work.

        1. jmkenrick*

          Right, I’ve always worked customer service, so I certainly take your point; but I do think it’s a very blurred line. I realized I’m just one data point, but I am actually friends with many people who I’ve met through work.

          I definitely advocate making any sort of social overture carefully and without undue pressure, I just don’t know that I can agree with the voices advocating for blanket ban.

        2. pony tailed wonder*

          Yes. My boyfriend has told me many stories about the waitresses who were in love with him when he was single and I just shake my head in amazement. I have told him what it is like to be a woman in a customer service environment and he thinks I am exaggerating.

    2. phillist*

      I think the thing here, is that–like someone posted upthread–“hitting on” versus “asking out” and what constitutes the line between them is subjective. Many of the people who perpetrate this type of thing wholeheartedly believe that they’re having a fun, reciprocal conversation while the target is thinking, “oh my god, I’m not allowed to stop being nice to this person but ewwwwwww.”

      I waited tables for a very long time. Boy do I have horror stories.

      I think, for women especially, there is also the matter of fatigue. This happens to us (generally speaking; there are certainly exceptions) *so often* that it can feel predatory at our jobs, even if it really isn’t. If you’ve been hit on/propositioned once a shift for the past month, that one guy who is genuinely kind and interested in getting to know you is just going to be added to the “SERIOUSLY!?” pile. When you’re in a position where your continued success (and as a waitress, your actual ability to pay your eat/bills) is contingent on playing nice with people who treat you like crap day in and day out–and looking sufficiently enthusiastic about it, thankyouverymuch–the power dynamic there is way off. I’m sure there are plenty of wonderful people who have found their partner by asking someone out while they are at work, but I’m also sure there are plenty of people who have found partners by asking out their employees–that doesn’t mean the power dynamic isn’t there, and that we should generally caution against it as a result.

      2. mskyle*

        Honestly, I’d rather be “hit on” in a low-key non-awkward manner than “asked out” in an intense, awkward way. There are a million variables here.

        1. Ad Astra*

          I was thinking the same thing. Flirting doesn’t bother me as long as the conversation doesn’t get gross or rude. Asking me point-blank if I’d like to go on a date with you is going to make me feel really uncomfortable.

          But then, I’m from that younger generation of people who “hang out” instead of going on proper dates.

      3. eee*

        Also, I think waitressing positions in particular–or any positions where tipping is involved–are especially good examples of this. (disclaimer, I’ve never worked any customer-facing position, so maybe I’m way off). I would assume that say, a Chipotle employee would probably feel way less pressure/expectation as part of the job to be friendly in the face of gross hitting on, because their wages aren’t as reliant on the customer’s decision to tip/not tip. The power differential is still there–depending on store management, the customer still may have the power to get this person yelled at/fired–but it’s a lot less so. Versus waitstaff who are being grossly hit on by customers know if they go “stop talking to me like that”, they just cost themselves the tip.

        1. eee*

          er, to clarify, where tipping is the majority of the income. I know you get tips at chipotle, but that’s a bonus that’s split by everyone in the restaurant, not the source of your income.

          1. As an aside*

            MMmmm… Chipotle. Make me a good burrito, and you will always have a platonic place in my heart.

    3. Daisydot*

      OP here, thank you, and yes I’m definitely not interested in objectifying this person or treating him like a piece of meat :)

  9. Anonymosity*

    I did this once as the employee asking out a customer (there was no rule against it), and he said “You should know I have a girlfriend.” Then why the hell were you flirting with me non-stop for days? Idiot. Clearly your girlfriend didn’t know you were doing it.

    Speaking of which, if someone at work–customer or coworker–asks you out, and you don’t want to go, EFFING SAY SO. Don’t say, “Sure sounds good! I’ll text you!” and then not do it. >:(

    1. Kathryn T.*

      I don’t know about that– there are people who will turn a refusal into a Giant Drama Explosion, sometimes to a frightening degree. I don’t think it’s fair to ask people to voluntarily take on that risk at work when there’s another approach that will neatly avoid that issue.

      1. Anonna Miss*

        Ummm, I with Kathryn T.

        If you put someone in an awkward position by asking them out when you aren’t really sure if they’re interested, then you probably shouldn’t be mandating (even in your head) how they are to respond. Talk about power dynamics.

        And yes, some people take outright rejection very badly. Thus the popularity, especially by women, of “letting them down easy”. It beats the risk of getting a “What, am I not good/rich/tall/whatever enough for you, you bitch?” response. A response that is far more common than a many guys seem to think.

        1. Elizabeth West*

          I don’t know; it’s easy enough to say, “I’m sorry, I have a policy of not dating coworkers/customers.” If your work doesn’t allow it, that’s an even easier out.

    2. Anonymosity*

      Well FWIW, I backed off immediately. It doesn’t matter anyway, because it will never ever happen again.

    3. TootsNYC*

      Then why the hell were you flirting with me non-stop for days?

      For fun and entertainment?
      Because it’s *just* flirting?
      Flirting is fun!

  10. saby*

    AH this reminds me of when I went out to brunch with a friend and she picked the restaurant and as we were walking up to the door she turned to me and said, “Well, I can’t promise I won’t ask out our waiter before the end of the meal!” It turns out she was a regular at this place and had a huge thing for a waiter. Who, granted, recognized her because she was a regular, and they had a bit of teasing banter going on which maybe had an undertone of flirting? But STILL. She has never worked a customer service job before so I guess the implications didn’t occur to her? Anyway, I begged her not to ask him out, at least not while I was there because I have been put in that situation at work before and I wanted no part of it, and especially not before we paid because I was worried he might think his tip depended on his answer.

    She eventually ended up asking if she could add him on Facebook and then sent him a Facebook invite to a party she was having, which he showed up to with a date. Aaaaaand now my friend is no longer a regular at that brunch place.

    1. neverjaunty*

      Mad props to the waiter for bringing his date to the party.

      Hitting on people who depend on you for tips is low.

  11. KT*

    This is so uncomfortable to me. I don’t what it is about retail–perhaps the forced friendliness-but it just seems like everyone thinks we’re dying for dates and I would get asked out constantly. I don’t really care how kind you are or subtle about it–it’s still off-putting. I’m trying to earn money and pay rent–not find dates. It puts me in an awkward position, and moreover, I don’t want to feel sexualized at work.

  12. Moss*

    Yes, retail employees get hit on a lot, but on the flip side, I always thought working retail was fun because I got to meet some cute guy customers.

    I wouldn’t give a lot of credence to the signals in a retail environment, because as others have stated, it’s his job to be solicitous. I personally wouldn’t ask him out directly, but would drop some hints about what you’ll be doing over the weekend (movies, wine festivals, coffee shops, etc.) and some comments like “have you ever tried the _____? It’s awesome. You should try it sometime.” so if said gentleman wishes to run into you outside of work he would have a pretty good idea of how to do so. That way he can take or leave the indirect invitation and doesn’t have to feel uncomfortable.

    ( However, I wouldn’t give too much info about the places you frequent, just because you don’t know him that well. Unfortunately there’s always the potential that someone could turn into a stalker.)

      1. TootsNYC*

        But if he were really, really interested in the girl, might he not go to those places hoping to run into her?

  13. Retail Lifer*

    About a decade ago, I worked in a store that had mostly male customers. I can’t tell you how many times a guy mistook my friendliness for flirting with him. But I can admit to having a thing for ONE of my customers, so I can’t say it never happened.

    I would hate to tell you not to try, though. Can you try something more neutral, like inviting him out to hang out with you and a group of friends? Or (I’m being serious here, even though I’m in my later 30’s) add him on Facebook? You need to determine if he’s being friendly because it’s his job, because he’s naturally flirty, or because he’s actually interested in you. I think you’ll only figure that out if you can talk to him outside of work.

    1. TootsNYC*

      Ooh, get a few people to go to a bar in the mall, and ask him to join you all after the shift.

    2. Daisydot*

      Thanks, I’ve definitely had guys mistake friendliness for flirting so I know what you mean. But this guy isn’t at all flirty; he’s kind of intense even though being flirty at this job would be perfectly acceptable. If he were flirty I doubt that I’d take him seriously. It’s a very weird situation and I agree with you that I need to speak with him outside of work in order to figure out what’s going on.

  15. Vancouver Reader*

    I did it once. I was in my 20’s and it was my last day at my summer job, so I wouldn’t have seen him again, at least not for an entire school year, provided he’d still be doing retail the following year. I had my co-worker give him a note from me and he did call me up. We went on a couple of dates, but that was it.

  16. Kelly L.*

    I was on both sides of this in my misspent youth. It did not go well. Alison’s advice on how to make it low-pressure is good.

  17. Nanc*

    I’m in the don’t do it camp because if he says no, you’ll both feel awkward. Am I the only one remembering Taylor the Latte Boy and Lisa the Stalker Chick songs? (Not that you’re Lisa, OP, just that it’s a humorous musical way of showing how two folks interpreted the same interaction!).

  18. ajw*

    When I was in college, I had a crush on my bank teller because I was there fairly regularly and we always chitchatted and flirted. The local pop/rock station was throwing a concert and I had extra tickets and invited him to come along with my group of friends. He came and then asked me on a date afterward. Inviting the person to a group thing seems way more comfortable than asking them on a date, in my opinion.

  19. BRR*

    Usually I prefer directness but this might get awkward if you go there often plus retail employees get hit on a lot. An alternative which isn’t great could be posting a craigslist missed connection and somehow very strongly hint about it next time you see him (or see him then post the missed connection). I’m not sure if this is a good compromise to not passing up an opportunity but also not putting pressure on him at work.

    1. Almond Milk Latte*

      The thing with Missed Connections is that 99.9% of them tend more to the ‘I’d love to take a swig from your Chocolate Teapot! Call me, you teapot vending minx’ side so even if you DO post something really innocuous, you still get painted with that really gross paintbrush.

      1. Kelly L.*

        Yeah, that’s a sitcom episode waiting to happen. The OP posts an innocuous “I see you every day at the 7-11 and I think you’re cute” but the employee thinks she posted the one that lists off 200 acts the Kama Sutra never dreamed of.

        1. Moss*

          That’s a great idea. Too bad The IT Crowd is off the air, I could totally see them doing a show like this one.

          1. Jade*

            When I saw your name The IT Crowd was the first thing I thought of!

            I miss Roy and Jen too…

            1. Moss*

              I named myself after Moss because I missed him. :(
              I love that show, I wish they would bring it back.

          2. Alison Hendrix*

            Didn’t Jen have an awkward flirtation with this barista at a coffee shop? That was hilarious.

      2. BRR*

        That is a concern I had thought of. Maybe write something along the lines of, “I did this so it wouldn’t be awkward while you were at work and I know it’s kind of strange but I wasn’t sure how else to contact you more discreetly.”

        Also OP, I wonder if you have looked for him on online dating sites?

      3. JMegan*

        Now I’m wishing I were single, just so I could use “Call me, you teapot vending minx” as a pickup line!

        If nothing else, it might be a good way to screen for fellow AAM readers…

      1. phillist*

        It has majorly given way to the “You brought me my omelet and now we’re SOULMATES” crowd, or–at least in my city–people not-so-discreetly trying to find prostitutes they used to, uh, frequent (that came out awful, but I don’t know how else to put it).

  20. manybellsdown*

    It’s not only retail – I was once asked out repeatedly by the older brother of one of my students! I was a good 10 years older than him AND he knew I was engaged because after the first incident I made sure to mention it. Only … he didn’t stop asking me out.

    Eventually he came to pick up his little sister on a day I happened to be out sick. My substitute said he was in a suit and had drenched himself in cologne. He got aggressive with her when he found out I wasn’t there, demanding to know where I was and when I’d be back. I think he was banned from campus finally because I never saw him again.

    So if you do this, and he says anything that’s not an enthusiastic yes, please reconsider shopping there again. It was actually terrifying wondering if he’d show up again.

    1. Many lols*

      Oh gosh… students. Oy vey! They would try to dazzle me with charm, I would kindly redirect them to dazzle me with good work. Thank goodness none of them ever tried anything like this, you poor thing! Yuck!

    2. katamia*

      Yeah, I used to teach adults and I was asked out BY A STUDENT. On my first day of teaching ever. Eurgh. He was removed from my class after that, thankfully (although it took awhile because I didn’t report it to my bosses until after the class had ended and then he didn’t come back for a couple weeks, and I was definitely nervous about him returning and nervous again when he showed up and I had to say, “Boss wanted to see you”), and one of my bosses came around and did a brief talk to all the classes without naming any names basically saying, “People, don’t ask out your teachers.” Which was really the best boss reaction I could have asked for, but still, ugh.

  21. anonanonanon*

    Please think very carefully about about out a retail employee. I worked a lot of retail jobs during middle school, high school, and college, and it’s unbelievable how many people misinterpret someone being polite and friendly as flirting. Retail employees have to be nice to customers. They have to smile and pretend like everything you say is hilarious and engage in chitchat. I think people sometimes forget that retail employees are supposed to act like this, but then, a lot of people assume that if a woman is smiling at you, she’s obviously interested in you, so….

    I hated being asked out when I worked retail because it was awkward and there was never anywhere I could escape to after I said no. Having people try to flirt or ask me out when I was behind a cash register was the worst. At least if I was cleaning up aisles or stocking shelves, I could pretend to escape into the backroom. Even when people flirt, there’s this mentality that retail workers have to just play nice and be polite, which is often construed as flirting back. It’s pretty much a lose/lose situation all around.

    One dude at the bank I worked at in college asked me out over the intercom in the drivethru teller’s lane and then got angry because I smiled and wished him a nice day whenever he came by. THAT IS NOT ME FLIRTING OR LEADING YOU ON, THAT IS ME DOING MY JOB.

    I’d hesitate against saying don’t ask the employee out entirely, because sometimes asking someone out can lead to good things, but I’d definitely caution against relying only on signals within the store as the basis for his interest. If the only conversation you’ve ever had is the normal chitchat when he rings up your purchases.

  22. RMRIC0*

    When I worked in retail, I probably would have been flattered if someone hit on me – but I was a teen boy. Now I tend to err on the side of “it is their job to be nice and their job is shitty enough without you slipping them your number” so short of them jumping in my lap I just let it go.

    Though after doing some work in an environment where the employees were supposed to be *extremely* “friendly” I realized you have to adjust your signals to the environment or it gets real awkward.

  23. nona*

    I know I have a weirdly strong opinion on this, but no. Do not do this in a situation where someone can’t leave or can’t answer 100% honestly (positive or megative). Try it if you meet somewhere else.

  24. the gold digger*

    It can end well! My friend Ilene always talked to the cheese manager at her grocery store. She thought he was attractive and they got on well. But he wasn’t asking her out. She went to Spain on vacation, bought a bunch of cheese, and casually mentioned it to him one day, saying, “It might be fun for you to come over and try some of it with me.”

    They have been married for almost ten years and have three year old twins. They are so well matched – it was bashert.

    NB They were both well into their 30s when they met.

    2. Daisydot*

      Thanks for that inspiring story; your friend is a smooth operator! And I love cheese but don’t have any from Spain. I’m going to have to think about this one…

      1. the gold digger*

        And a friend of Ilene’s – another pediatrician – really liked the farmer who sold his sweet corn at the farmers market. Every week, she would buy a bunch of corn and talk to him. She thought they got along OK and that he seemed interested, but he never asked her out.

        Finally, she asked him out. He was confused – she asked, “Did you really think one person could eat that much corn?”

        Now they, too, are married.

        I think they key with both couples is that there were adults and past the minimum wage jobs. That is, Cheese Guy was not an 18 year old cashier, he was the cheese manager for the chain. And the corn guy had his own business. So the power dynamic is not so different.

        You could use Wisconsin cheese. :)

        1. J.*

          Hahaha. I’ve never worked in retail and don’t really have the personality where I would feel comfortable asking somebody out first, but I really like these stories! So cool how well they turned out. :)

        2. Daisydot*

          LOL “did you really think one person could eat that much corn?”. That is classic. And it’s so true; it can be tricky to know if someone just really likes corn or really likes you.
          Thanks for another positive story!! I can’t figure out a way to work cheese into this at all though, unfortunately :) I know what you mean about the manager thing: he’s older and it’s one of those places where managers are expected to do everything that their employees do so I don’t know if he is or not. I can find out though and that might make things a little less fraught, dynamics-wise, if he is.

  25. catelyn snark*

    IMO, it is always 100% creepy to ask out a server/service employee waiting on you, period. That person is required be there and is required to be attentive/kind to you– and to every other customer. Nope nope nope never ok.
    Check out this blog post for an eloquent statement about this: http://captainawkward.com/2011/07/04/blanket-statement-monday-stop-hitting-on-the-waitress/
    (sorry if posting links is not ok; it’s a Captain Awkward post entitled, “Blanket Statement: Stop Hitting on the Waitress” so you could google that.)

  26. T*

    It sounds to me like OP is being very conscientious about the situation. I’m in the school of thought that the fact OP is concerned about how it will be received probably means she’s fine to move forward. The guys I know that routinely hit on female retail/service workers do it in the blink of an eye the second they see a pretty face. They don’t look for or even care if they get a non-verbal clue she is interested.

    And this is an obvious double standard but I think it’s less of a big deal because the manager in question is male. A lot of comments here are from women saying they get hit on non-stop (and I don’t doubt that) but I don’t think that really happens to guys (with the except of a select few).

  27. Io*

    Listen, I’m coming out months’ worth of lurk-hiding just to say: nooooooo! Please don’t do this! It is so awkward for the person behind the counter on so many levels, and honestly, if it were me back when I was working retail I’d be terrified that if I said no, you’d do something to get me written up or contact the district manager to get me fired. Admittedly, my old district manager basically fired anyone who had a direct complaint made about them no matter how ridiculous (seriously), but these thoughts would all run through my head and I’d be scared my livelihood depended on saying “yes” to a date with someone in whom I am potentially not interested in at all. It’s not a situation I would want to be in and I’d never want to do it to someone else.

  28. LPBB*

    This is coming from a woman’s perspective, so take it with a grain of salt.

    I used to work retail and used to get both hit on and asked out a lot. The majority of guys were creepy and it was a huge irritant, especially if they were repeat offenders. There is a certain subset of people who enjoy exerting their power over people in customer service positions, and a fair number of men in that subset will “flirt” with women in customer service as a means of exerting that power. I have no idea if men in customer service experience this as well, but I know the men that I worked with almost never dealt with unwanted sexual attention from customers.

    However, there was one guy that asked me out that I totally would have gone out with, if I hadn’t already been dating my now-husband. The key difference was that he had been coming into my bookstore for at least 6 months and chit-chatting with me about stuff, usually books but other things as well, before asking me out. So I had the chance to get to know him a little bit, he got to know me a little bit, we established a rapport, etc. He was also very cool when I turned him down and he kept coming into the store, albeit maybe a little less frequently, and chit-chatted like nothing had happened (except for my red face because my face is my own worst enemy).

    The point to all of that is, it is possible to hit on/ask a retail worker out without being creepy. I definitely agree with all of the suggestions about keeping casual and low-key and, if he turns you down, continuing to interact with him as though nothing happened.

    1. Daisydot*

      Thanks, I agree that being cool about it and reiterating that a refusal is fine is the way to go!

  29. Jo*

    I worked retail throughout high school and college. I worked in a large grocery store chain that prides itself on “premier” customer service. I was 19 and very naive when a customer a few years older asked me out. We dated for close to a year, and when it ended, it did not end well. He was driving through the parking lot at work, waiting by my car, leaving things at the customer service counter for me like cards, flowers, etc.. it was extremely uncomfortable not just for me but for my coworkers who were forced to be nice to this creep.. and yes, he’s certainly a creep. Even when we were together, he’d come by to check up on me, he’d get a little bit jealous if he saw me talking to other guys. He was never angry or aggressive when we were together, just smothering and overstepping his boundaries.

    In the last few years, I’ve had men ask me out, and although flattering, they’re usually significantly older than me (40’s and 50’s even) and it puts me in a very awkward position of turning them down. I’m nice and can have a very bubbly personality, and it really frustrates me that men would assume I was flirting and ask me out. It made me question my behavior and be mad at myself for smiling a lot and just being casual and courteous. But ultimately, I can’t change who I am nor should I.

    So now that I’ve rambled, I just hope the OP really considers this person’s demeanor before putting him in a potentially awkward situation. There are those rare occasions where it works out and they get married and live happily ever after, and I’m an absolute sucker for those stories of taking a chance and it working out wonderfully. I guess I’m just a bit pessimistic in that it rarely happens that way. Be casual, play it cool and do not put pressure on it, and I’m saying this because I think you’ll go through with it. I like some of the advice above with the whole, “I’m thinking of doing this, maybe you should come join if you’re free,” and bonus if it’s with a group

    1. Daisydot*

      Hello, OP here. I know what you’re saying about the stalking: I’ve been there myself and would never want to put someone in that position. This guy’s comfort level has been a huge concern of mine. I agree that the group thing could be a good, low-pressure way to go.

  30. Aaron*

    From a quick skim of the comments, it seems like I’m in the minority opinion here (I’m a man myself), but two things:

    1. I don’t think that asking someone out — if done in a not creepy way — is anything like being hit on. Certainly, it can be that way, but to me, I’d take being asked out as a form of flattery, even if I wasn’t interested.

    2. I don’t understand why asking someone out has to be interpreted as some sort of sexual/relationship-driven ritual. You don’t know this person, they don’t know you! I’ve always thought of it more as, “Hey, you’re someone that seems to be intereseting, and I’d like to get to know you better.” (Actually, kind of like a job interview in a lot of ways, haha. Each party is still evaluating the other.)

    3. This is why I always do coffee or something comparably simple/safe (so not dinner, movies, etc.) when I’m meeting someone new. If they’re creepy, weird, or not someone I’d be interested in getting to know better, there’s an easy out. If I get “friend but not relationship” vibes, then I can always invite them out to social outings in a group in the future! And if there’s mutual chemistry, you can always get dinner/drinks/etc. after coffee.

    So if it were me, I’d just say, “Hey, would you want to grab coffee sometime?” If they say no outright, or if they say things that imply that they’re not so interested (“I don’t know, my schedule’s kind of crazy” etc.), then drop it, and to me, it’s no big deal. Like I said, I’d be flattered, even if I was interested — and it wouldn’t be weird for me to see you again in the future.

      1. Erin*

        I agree. If done in a non creepy way and they gracefully accepted my no, I would be flattered. It’s be a nice pick me up for the day.

    2. Joss*

      The problem is that all the good intent in the world doesn’t really change how the service person being put on the spot is going to react. Working retail, this happens so, so frequently that it stops being flattering and becomes another work annoyance that you have to deal with, plus the unease of not knowing how someone is going to react if you reject them.

    3. Pretty Torn, overall No*

      I mean the problem is that it happens way more often than you think. It stops being flattering at a certain point, and even then there is ALWAYS the pressure of “I’m at work how can I respond in a way that will keep this persons business and not cause a scene and get me in trouble with my boss?”

      The customer could respond in a perfectly reasonable manner after being turned down, but the employee will still be extremely nervous about the exchange.

      I will put a quick disclaimer/bias I am female, and I think women overall have to deal with this more than men, so it’s probably why it’s more annoying in my mind.

      1. phillist*

        I’ve seen a lot of this sentiment in this thread (“I’m biased; I’m female”) and I just want to say:

        That isn’t bias; it’s perspective.

    4. anonanonanon*

      A lot of women don’t find being hit on or asked out by a strange man flattering, especially if the most conversation they’ve had with them is either mundane chitchat or about the customer’s order/purchase. You rarely get a sense of whether someone’s interesting when they’re being polite or friendly due to the nature of their job.

      Women deal with this sort of stuff all the time – at work, in public, going about errands, etc. – and it becomes incredibly annoying and frustrating. Some people may have good intentions and be okay with a rejection, but there are a lot of men who aren’t and turn vicious if they’re ignored or rejected. This is bad enough in public, but it’s a bit worse if you’re being put in that situation at work.

    5. Panda Bandit*

      Just because you would find it flattering doesn’t mean the service worker feels the same.

    6. neverjaunty*

      ” but to me, I’d take being asked out as a form of flattery, even if I wasn’t interested” – This crap makes me want to flip tables. You’re visualizing a very specific scenario, where you’re ‘being asked out’ in a very nonthreatening way, presumably by having a woman express interest in you, which doesn’t happen so much in a culture that discourages women from doing this.

      Instead of just insisting you’re a dude and this is how YOU think, maybe try putting yourself in other people’s shoes? When people tell you over and over again that this behavior is not flattering or OK, replying with “Yeah, but *I* wouldn’t feel that way” is about the opposite of empathy.

      1. anonanonanon*

        It’s like when people say that women who are catcalled should feel flattered and that they’d personally feel soooo flattered if they had strangers harassing them on the street. Ugh.

      2. Erin*

        This seems like a bit of an overreaction to someone stating their opinion in a non-rude or abrasive manner.

        I took his pointing out he’s male as, “Hey, I’m a dude, so take what I’m saying with a grain of salt, but this is what I think…”

      3. Aaron*

        I consider myself a pretty well-centered person. I have a fair number of female friends, and many (I’d wager most) feel flattered when a man approaches them confidently and in a not-creepy or inappropriate way. So I definitely don’t think it’s fair to allege that I’m not empathetic here — I’m reflecting on my own feelings as well as those I’ve heard from others of both genders, or as you say, “putting myself in their shoes.”

        1. neverjaunty*

          Except this is not a conversation about whether it’s ever OK for a man to approach a woman “confidently and in a not-creepy or inappropriate way”*; it’s a conversation about a specific situation, namely making romantic overtures to somebody whose job and paycheck require them to be pleasant to you.

          *Setting aside the whole discussion about what is and isn’t ‘not creepy or inappropriate’.

      4. Chalupa Batman*

        I think Aaron indicated clearly that being flattered is tied specifically to an appropriate non-creepy invitation; he didn’t suggest that any type of behavior is flattering as long as there’s romantic interest. As a woman, I’m also flattered when I’m politely asked out, even though I do not accept the invitations (I’m married). That doesn’t mean that I feel the same way having crude comments shouted at me on the street. I can see where you’re coming from in general, and I apologize if I’m misreading you on this, but I hated to see Aaron take the fall for all men because of word choice. I did think your point about women being discouraged from asking men out was really interesting. It definitely impacts what might feel flattering versus intrusive when you come from a male context, where there isn’t the automatic feeling of “what do you want? is this situation safe?” whenever someone flirts with you. That context is something that men need to be aware of when deciding it’s ok to flirt with a woman in a particular situation-which I think is what you were getting at.

      5. Jennifer*

        Think of it this way: can you think of someone you think is genuinely rather awful? Imagine if they asked you out. Would you feel “flattered?” I do not so much when it happens to me.

    8. Stranger than fiction*

      See that’s how it should be and how it generally happens in my world, but I’m getting the impression that these days there’s a lot more creepy people out there and like I said earlier that’s just sad that our world has gotten to the point where people assume the worse first and not the other way around.

    9. Daisydot*

      Thanks Aaron, I’m the OP and appreciate your male perspective on this! It’s great to know that you’d be flattered (even if not interested)!

    10. Sarah*

      Re 2, though, if you don’t know them, surely it is ONLY sexual? The only thing you know about them is you’re attracted to them physically, and they are friendly when you’re in the shop (which should be the standard for any customer service staff). The whole “you’re great, I want to get to know you, total stranger I buy my latte from” is understood by 98% of the population as “I want to date you”, which is, to 98% of the population, implying sexual interest at some point (and the asexuals I know make it upfront that they’re NOT after a sexual thing)

  31. Joss*

    Please, please don’t do this, OP.

    I have no doubt that there are some rare instances where this has worked out and the couple is now happily married with three kids and a dog and a white picket fence. But it’s so much more likely that any given service worker is being nice to you because their continued employment and paycheck is dependent on being nice to you.

    And for what it’s worth, having been a barista and worked at Target, there really wasn’t any appreciable difference between being asked out and being hit on. Both scenarios happened to me multiple times and it was always uncomfortable and always put me in an intensely awkward situation. The pressure to respond positively to those interactions to avoid A Scene is so high! I had one regular while I was a barista ask me out in what seemed to be a sincere way, but when I turned him down then showed up every single goddamn day and stared at me for almost a month.

  32. JoJo*

    It’s a place of business, not a singles bar. Please don’t hit on the poor schmuck who has to be nice to you or get fired.

  33. Ad Astra*

    My brother-in-law met the woman he’s about to propose to when he was an employee at a grocery store and she was a customer. So I guess it’s possible for these things to work out. I do know that she had been coming in once or twice a week for months before anyone made a move, and I know they had been chatting a lot more than your average employee and customer would chat (to the point that I wonder how he wasn’t reprimanded for not doing his work). At some point, she told him “Hey, I have this song I think you should hear but I forgot to download it onto my phone. Can I add you on Facebook and send you the link?” So she added him, they talked until 4 a.m. on Facebook messenger, and they went out a few days later.

    That’s a lot different from walking into a store and asking someone who’s rung you up at the cash register three or four times to go to dinner with you. Even if you think this guy might really like you, you’re going to have to take it slow.

    And the safest answer is still “Don’t do it.”

  34. SerfinUSA*

    Oh man! I almost forgot about the boy from the produce department!
    When I was newly single (and loving it) after an early, long marriage, I ended up chatting regularly with a nice and nice-looking young man who worked in the produce department of my usual grocery store. We made plans to go to a local haunted house together in a couple of weeks, but a conversation in the meantime put the brakes on that.
    I thought he was over 25ish, he though I was under 25ish. Um nope and nope. He was 20 and I was 32. We laughed and decided best to keep things at friendly store chats. We were both flattered though and it wasn’t awkward.

    1. Daisydot*

      OP here, thanks for sharing your sweet, funny story. Sorry to hear that it didn’t work out (a haunted house would have been a very cool first date!) but it’s great that you remained friendly.

  35. Pretty Torn, overall No*

    Alright so… I used to work retail. It was my first job ever, I worked part time for a store that primarily sold video games and video game accessories. I was the only female that worked there, and getting hit on generally happened in two categories.

    1) I was a girl and that was enough to get comments
    2) I would be told “wow you actually play video games?” while striking up a conversation trying to get the customer to reserve an upcoming title or subscribe to our magazine or whatever.

    So… sorry to say, for me at least, the perceived romantic connections were not real. It was very intentional for me to talk to you about games. Yes, it was a common interest, but I also had a certain number of reservations and sales I needed to make. It was a required part of my job.

    Granted, yes I loved talking about video games. I loved the store and my job and loved that part of it was to talk about my interests with customers who shared those interests. But I didn’t love YOU.

    Needless to say, I got hit on a LOT. And it was always a minefield to navigate. I hated that aspect. I also had people hang around the cash register after I had finished ringing them up try to continue to talk to me. This is while there were a line of people waiting for my attention. It was extremely frustrating.

    The only reason I’m torn at all is because I’ve also heard the stories of people meeting their husbands/wives through these connections. But, I got hit on so frequently, I would have loved to stop it.

  36. Erin*

    I think you should go for it, but I’m optimistic like that.

    You could try to get friendly with one of his coworkers to find out if he’s single, and possibly also when his break is or when he gets off work. Obviously you don’t want to be creepily waiting for him by his car or something, but it could give you a chance to ask him out while he’s off the clock.

    I once had a crush on a guy who worked in retail. One time when he wasn’t there I said to his coworker, “Hey, is the cute guy working today?” She told him I had asked about him, and the next time I went in he gave me his number.

    1. catelyn snark*

      This is different, though, from approaching the object of affection. In this case, the crush could have ignored it. I still think it’s creepy to approach the crush him/herself, when they’re obligated to be nice to you.

  37. msbadbar*

    OP, I did this once. I had a long conversation with a nice guy at a mom-and-pop camera store, and I felt intrigued. I was also wary for the same reasons you are. No one wants to be a creeper. What cinched it for me was my dad who was there with me. After we left the store, my dad muttered, “well, he seemed to like you ok.” (Sidenote: my dad and I never, ever talk about anything remotely related to me dating. He is incredibly shy about that kind of stuff. I felt like if something could prod him to say that, I must not have imagined it.)

    I had to go back to the store later that week to pick something up. I wrote write my info on a small piece of paper and said something as non-pickup-y as possible: “If you want to talk more about photography, here’s my info” or something. I also made sure none of his co-workers or any customers were nearby.

    Result: He emailed me that night, and we struck up a friendship, but never dated. (I was visiting my hometown, where he worked, but I lived pretty far away.)

    Anyway. I think it can be ok if you do it very carefully.

    2. Daisydot*

      Thanks msbadbar, I loved your story, especially about your dad! Yes I definitely want to be cool about it and subtle and your story is inspiring! :)

  38. Alice*

    You could try asking them out if you happened to run into them outside of work, however, they know who you are so it still makes it awkward if you go back to where they work. But what if you realllly like this person? I think that is the difference. People shouldn’t just ask anyone everyone they find the least bit attractive while at their place of work but I think it is different if you think you could really have a strong connection with this person.

  39. Case of the Mondays*

    My female friend just started dating a waiter we met while out to eat. The way she did it was to grab another waitress and say “hey, I’d like to give my number to our waiter. Do you think he’d be into that? Is he single?” The waitress said he was single and that he’d love to get a number so we left her number with her credit car receipt. The waitress could have said “oh, he’s off the market” or he gets number all the time and is sick of it or something like that so it would avoid the embarrassing interaction if there wasn’t a chance for a positive outcome.

  40. Demanding Excellence*

    Long ago, when I was in college, I asked out a nice, cute guy who worked at a retail store I frequented. He gave me his number and I called him to make plans. He told me that he had a girlfriend but they were “on the rocks” currently. He also said if that he would be interested in going out with me if they actually broke up. I was so, so embarrassed and hung up the phone immediately.

    My SO is a manager of a retail store and gets attention from customers (both male and female) on a regular basis. He’s always nice and professional, but makes sure that his suitor knows that he has a serious girlfriend. Most people take it well…except for this one guy who literally followed him around the store, essentially catcalling him and making really inappropriate comments. :/

  41. marxamod*

    Life rule: never hit on someone who is being paid to be nice to you.

    It’s hella awkward for them and unlikely that the connection you’re feeling is real. If they’re interested they will, specifically, ask you. (This doesn’t include asking for your number when filling out a form for the job.)

  42. Anonymusketeer*

    I’m married, so I definitely wasn’t going to ask out the cute liquor store employee who likes the same kind of beer I like anyway. But it was a bit of an eye opener when I saw him making the same friendly conversation with another beer-loving female customer. Sometimes it’s just part of the job.

    1. TootsNYC*

      That’s a point–as the OP is gauging this guy’s interest, she should observe how he acts with other customers.

  43. _ism_*

    I’ve been pondering this exact situation, in regards to the guy at the corner store I go to. It’s been over a YEAR since I had the nerve to try dating or asking anyone out and I had just decided it’s going to be this guy. Meh. Good thing I didn’t leave work yet :/

    1. Daisydot*

      _ism_ OP here, I know where you’re coming from. There is some amazing advice here, from so many perspectives. It’s really helping me to figure out what to do (and I’ve been debating this with myself for awhile now) and I’m really grateful that so many people chose to respond.

  44. Court*

    I’d have to look it up, but I think it’s actually prohibited at the gym I work at to ask out members. I realize this situation is reversed, but when I was single if I was asked out at the center the answer was, “I’m sorry, that’s not allowed.” Also, you weren’t allowed to give out your contact information either.

    Now if in chatting it comes up that you and your friends frequent X location on Saturday nights because you love live music etc, and they show up there to say hello or you happen to run into them elsewhere, it’s more of a grey area that’s more arguably okay.

  45. Bea*

    I also want to say DON’T DO IT! I was a bartender for many years and the worst thing about my job was the endless flirting and customers asking me out on dates. But I will also say I met one really great boyfriend while working.

    If you are really interested and you think this guy could be something really special then there is a gentle way to go about it. Write your number on a piece of paper, have it ready when you go to the store. The next time the store is slow and he rings you up when you’re the only person in line– have that piece of paper ready. When he’s done ringing you up say something that acknowledges how weird what your about to do is and then state that if he never calls you that’ll be cook and you can both forget all about it forever. Do NOT make any comments about their physical appearance, that will make it weird forever. An example could be, “Hey so this is going to be super weird. I’ve seen you in here a lot and you seem like the type of person I would like to get to know in real life. Here’s my number, no pressure if you’re not interested. If you don’t call we’ll forget this ever happened.”

    You can only do this is you won’t be crushed by rejection and you won’t be weird the next time you go to the store. And if he doesn’t call you actually have to forget the incident ever happened, for real no joke you actually have to. So if you can’t do that, or you can talk yourself into just enjoying the eye candy, don’t do it.

  46. Alison Hendrix*

    I remember the last time we were shopping at an REI – a lady cashier (I’m guessing who also assists with the wall-climbing area) was talking to a guy (I think who also works at the wall-climbing area too). The guy was CLEARLY crushing on her, he was like he “forgot” something at the store so he came back, and proceeded to just chat further and she was smiling and just allowed herself to be responsive. She was very nice, but I didn’t get the vibe she was interested in him as well – she seemed to just be doing her job as being accommodating. I was watching the whole scene unfold and he was trying his best to extend his little chat with her by just grasping at whatever topic he could think of in this sheepish, gigglish tone, and her simple responses back to him without breaking a smile, while also ringing out my items.

    I mean – if I forgot something I would’ve just gone in and said, “I forgot this” and say my goodbyes again. Especially if whatever person I was talking to was clearly busy with something else.

    Holy cats, it was painful to watch him. But at the same time – “Dude, she’s trying to do her job, and you’re kind of holding her up…”

  47. Ashley the Nonprofit Exec*

    15 years ago when I worked in retail customers asked me out all the time. Some were creepy. Some were way too persistent.

    I only said yes once, mostly because he was polite, unassuming, and I did not feel harassed – for a change.

    We’ve been happily married for 10 years.

  48. Kathlynn*

    I don’t know if I get hit on very often, Probably not since most of the male customers are either 5 years younger then me or at least 15 years older then me. But, try becoming friends outside of work first. Truthfully, then you’ll know if the other person likes you platonically, and if you like them. And you might realise “hey, I only want this person as a friend”. And then poof you have a friend, and can still visit the business.

  49. Macedon*

    Only ask the gent out during his break or free time. Don’t put him on the spot by forcing him to balance customer service with a romantic overture – it’s unfair to him. Even if you don’t mean for this to be the case, you are in a position of power when you are his client, and it’s inappropriate to initiate something like this when you’re not on equal terms.

  50. Former Cable Rep*

    I’m not going to say to absolutely not do it, but I recommend asking him out somewhere other than his job if you see him elsewhere. At his job, he has to be polite. He may truly be interested but the power imbalance there makes it sort of uncomfortable. At a bar, after church, at an event where you share a mutual interest, go for it! Whatever you decide, I wish you luck.

  51. HR Caligula*

    Late in the thread but don’t do it while they are working their CS role.
    My older sister took a bank teller job when I was in my early teens and I recall her complaining of guys hitting on her simply because she was pleasant in manner and appearance. It’s my practice since to never pursue workers in service, not that it matters so much now.

  52. mel*

    Just be subtle about it and see where it goes. There’s no reason to be too embarrassed to ever return upon rejection unless you’re either serenading the guy in a public show, or if you be otherwise dramatic or persistent about it.

    When I was a cashier, someone gave me their phone number. It was so non-creepy that I didn’t even realize it was a request for a date until the end of the day. We were having a polite conversation about video games, he left the store, and then came back from his car to give me his number “in case we wanted to continue the conversation”. And there was no pressing and he never followed up when I didn’t call. Seemed like a good method to me.

    (Of course, maybe he WAS too embarrassed to ever return, but I can’t think of why, because politely asking a person out isn’t embarrassing)

    1. Daisydot*

      Thanks mel, a friend in retail recommended the note thing; that’s how she began dating a customer…

  53. Kirsten*

    I think you should go for it. I liked the “slip him your number” idea that way you’re not publicly making it awkward for him, and you’re putting the ball in his court. If he doesn’t call/text then he isn’t interested and you can leave it at that.

    My friend once slipped her number to a butcher at a supermarket and they ended up married. You never know!

    Good luck!

  54. Helka*

    I’m gonna join the “don’t do it!” train. Unless he’s specifically told you about these things, you don’t know what’s going on in the background for him, and what it might raise.

    And here’s my story to support that: back in my retail days, I worked in a shop that primarily catered to women, and men coming in tended to get a bit of special attention since they were something of a rarity (and often needed a little extra help from the employees). I got asked out by a male repeat customer around my age who had always been polite, nonthreatening, was quite nice-looking, and very interesting to talk to.

    The problem? This was in the rural South and I was a very, very closeted gay woman. (Still gay, now not so closeted :D) So while I was able to stumble out a decline that didn’t out me and sounded fairly legitimate, the truth was I’d been rather blindsided, and I spent the rest of the day scared that one of my coworkers would have overheard and I was going to get grilled about why I didn’t agree to the date later on.

    Now, I’m 100% sure this guy would have been an awesome date, and there was nothing threatening or creepy about his approach — in fact, if I had any glimmer of interest in men in general, I probably would have taken him up on it. He didn’t have any way of knowing that his asking me out was going to be such an issue for me, but it still made work awkward and scary for a while, and I did my best to avoid him from then on.

    At the end of the day, I’m with Captain Awkward. Don’t ask out the waitress, or other person providing you customer service in order to survive. Just let them do their jobs.

  55. SWriter*

    Oh man, OP, I’ve been there.

    In Ohio, we have drive-thrus where you can literally drive through and buy beer, cigarettes, pop, etc. (Explaining this because some people look at me funny when I talk about going to the drive-thru).

    I went to the same drive-thru for YEARS and had a crush on the guy who worked there. We always flirted, he always asked me about what was going on in my life, on and on. I ran into him one time outside of work and he talked to me most of the night while his girlfriend sat in the corner and pouted. I always wanted to date him and ask him out, but I never got the courage until a few years ago when I found out we were both single.

    I flirted and flirted with him–I mean REALLY laid it on thick and I couldn’t figure out why he wasn’t responding. One night, I got all dressed up (hair in hot curlers and everything) and went to the drive thru to see him. I told him I was bartending that night and that he should come visit me, and I gave him my number. He seemed interested until I got a text from him later saying he couldn’t make it. I may or may not have drunk texted him after that and needless to say, we never ended up dating.

    I have to say, I feel bad for the pressure being put on men for the whole asking someone out thing because that was the first and ONLY time I have ever asked a guy out and I got rejected. And man did that sting. I avoided the drive thru for a few months after that but when I went back we both just acted like nothing had happened. It was awkward, but I realize now that I’m probably better off.

    TL;DR: I was 1000% sure this guy liked me, I asked him out and found out he didn’t. Then, awkwardness. I don’t regret it though.

  56. Bluesboy*

    As a man who’s been asked out 4 times by clients, I say go for it!

    For me, once was an uncomfortable first date, once was a few dates, no more, once was an amazing relationship and one turned into a stalker. But you know what? One great relationship made it all worth it!

    One thing. Remember where you are – sexy flirty behaviour leads to confusion where he isn’t sure if he understood, it’s so out of context. I once asked a girl to explain what she meant, when what she actually wanted to say would have been perfectly clear if we had been in a bar. Awkwardness all round…

    Good luck!

    1. Hit On*

      I’m hoping, for the employee’s sake, it didn’t.
      The OP only seemed receptive to posts encouraging her to do it though.
      Arrange to “run in” to someone as they are leaving, but asking them out in their place of employment is frankly awful.

  59. Liam*

    I am a 23 year old man and i want to ask a girl out that works in a clothes shop nearby where i live. If i ever did (which i wont because im too shy, but shes the most beautiful thing ive ever seen) ask her out and she said no, i wouldnt have a problem at all i think women are allowed to decide things by themselves and shouldn’t be pressured into saying yes or no. Surely there is someone out there like me, who is genuine and can take a no.?

  60. Will*

    I’m a male, nearly 30, and I have been going back and forth for weeks about somehow asking out this cashier at a grocery store I frequent. I’ve seen her about 10 times, but I realize she might get this a lot. The last time I was in, I said it was weird we didn’t know each other’s names by now, so I told her mine and got hers and the other cashier’s she was talking to. She said she knew me already and found it a little odd, but we always have a lot of eye contact and banter. I don’t want to put her into an awkward position – and I’m stuck between a note approach (“too pussy for a man”) and directly asking her out (“confidence”). It feels like a lose-lose situation. I have never asked an employee out or hit on a woman working before, and for some reason I think this woman is special, even though I don’t know intimate details about her life and vice versa. I don’t want to miss out if she really is as special as I’m feeling, but I also realize it might just be me feeling that. “There there” from Radiohead rings a bell. I’d love a woman’s advice on how to go about this, because I want to do it the right way for both parties involved. Thanks!

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