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How do I ask a complete stranger out while she's at work?
June 1, 2011 12:52 PM   Subscribe

How do I ask a complete stranger out while she's at work? Should I even consider doing this?

Here's the deal: I'm 26 (almost 27) and have never asked anyone out. I've managed to be married (5 years), have a child, get divorced, but I've never actually said, hey, do you want to go out and grab lunch? I'm the guy who, at anything social, will be sitting quietly - alone, more often than not. I suck with people and I hate it. My self confidence is quite low, and so getting the nerve up to do anything gutsy is nigh impossible.

I don't have very many real life friends, and I don't really do much of the whole "hanging out" thing. Not that I don't want to, mind you - just that I've never really done it much and so I tend not to be invited to such gatherings.

When it comes to women, I'm more or less clueless. I'm not good at reading signs, I'm not good at sending signs, and even if I were, I wouldn't really know how to follow up on such signs. I'm really, really shy, and am pretty awful at expressing how I really feel.

Now that you have an idea of what I'm like, here's the question: how do I go about getting over my stupid hang-ups and ask a complete stranger out, while she's at work? I know nothing about this woman other than I find her attractive, and I think she looks like she'd be interesting to get to know. Just a gut feeling, really. I've never seen her anywhere but at her place of employment, which happens to be a pharmacy. As such, there are usually 10 or so people buzzing around here all the time, so the chances of privacy are more or less null. Furthermore, she's never really shown any signs of being interested - this is most likely a completely one-sided thing, and I'm okay with that.

My concerns lie largely with 1) her well-being and feeling of ease and 2) how I should act if / when (the latter is far more likely) she says no. As for 1., I don't want to do this if it's going to make her feel like crap or make things really awkward from now on (I frequent this pharmacy fairly regularly). And as for 2., consider me a 9 year old or something in regards to this. If I ask if she wants to get coffee or something, and she declines, what do I say to make sure the conversation doesn't go kersplat? "Oh, okay"? "No problem"? "Thanks anyway"? "Have a nice day"?

Bonus points if you can help me figure out what my underlying issues are, because frankly, I hate being the way I am.
posted by menschlich to Human Relations (68 answers total) 9 users marked this as a favorite
 
There is no responsible way to convey romantic interest to someone in circumstances where they are professionally obliged to be polite to you.

Sorry.
posted by Trurl at 12:58 PM on June 1, 2011 [66 favorites]


As someone who has worked retail, and who has had the occasional customer express non-customer-y interest, please don't do it. It hasn't happened to me often, and only once has it been unambiguously creepy, but it's never left me without the feeling of at least a little discomfort in future interactions with that customer, and working in an environment like that blows.

You sound shy and inexperienced, and there's nothing wrong with that. Both issues are fixable, or at least workaround-able. If you don't want to dive into the world of online dating, see if there are interesting meetup groups in your area, and go to them. Practice talking to people who you already know are interested in things you're interested in (you're both at the meetup for Extreme Outdoor Knitting!), even if - especially if - you have no interest in dating them. Getting some practice in making friends, or at least friendly acquaintances, with strangers will help ease some anxiety and overthinking when it comes to actually dating. Ideally, anyway.
posted by rtha at 1:01 PM on June 1, 2011 [1 favorite]


This one has been rehashed several times on the green. Don't ask someone out while they are at work.

You can still have conversation with them, but don't put her on the spot. Put yourself somewhere that she might be out of work. If she is interested, she might ask you. Or she might clue you in on to where she might be outside of work. But don't do it at her work.
posted by Mister Fabulous at 1:03 PM on June 1, 2011


the times i have been approached at work and asked out were creepy and unwelcome, and made me feel unsafe in my work environment. please don't do this. context is key here: the best place to approach someone for a date is when you are on as even a playing field as possible. online dating, meetup events, parties, etc..
posted by hollisimo at 1:04 PM on June 1, 2011 [2 favorites]


It's extremely unlikely that this will work. When I was still in my twenties, guys occasionally asked me out at random and my thoughts were always these:

- At best, I don't know anything about this guy and it will be awkward to extricate myself if he turns out to be an awful person, racist, sexist, etc.

- He doesn't seem to understand/have access to normal ways to approach women, which means that he is more likely to have other social problems too

- He could be one of those guys who thinks that because he buys you a coffee he gets to feel you up or worse - I don't know anything about him.

- He knows nothing about me and so I'm basically interchangeable with any other woman he thinks is pretty; this is not flattering.

- If he's asking me out based on looks alone, he doesn't really prize compatibility, so is unlikely to be the fun partner of my dreams

I'm sure you're a decent fellow or you wouldn't have bothered with the question...but really, this isn't going to work well.
posted by Frowner at 1:04 PM on June 1, 2011 [33 favorites]


Yeah, the workplace situation is tough. I can't help you out there.

For what it's worth, though, I think there are very few people comfortable with asking other people out. The first time I asked out a woman (I'm a lesbian woman) I literally almost passed out from nerves. The only thing that got me to work up the nerve was knowing that I'd regret it the rest of my life if I didn't.

The woman I asked out ended up not being a lesbian. I won't lie to you- it was pretty much the most mortifying event of my life. However, I've never regretted asking her out and I'm definitely a better person for it. As to what to do when/if the conversation doesn't go in your favor- there's really no way to not make it awkward. All you can do is be gracious about it and thank you for her time. The girl I asked was very nice about it and, really, there's no reason not to be. If you're being polite and not creepy the girl you ask should be flattered and she should respond kindly. If you're nice and polite and she reacts like a jerk, then she's a jerk and you're better off without her.
posted by shornco at 1:06 PM on June 1, 2011 [5 favorites]


As such, there are usually 10 or so people buzzing around here all the time, so the chances of privacy are more or less null.

She's too busy to talk to you and asking her out would be a major intrusion. Nthing everyone else.

Furthermore, she's never really shown any signs of being interested - this is most likely a completely one-sided thing, and I'm okay with that.

Why? Why are you OK with that?

Here's how it goes if a woman is interested in you: she'll ask you about yourself. I guess if I worked at a pharmacy and I saw a cute guy, I'd ask stuff like whether you lived in the neighborhood, what your plans were for the holiday weekend, etc. Or I'd comment on something of yours - for example, if you're holding a coffee cup I might say "Oh, I see you stopped at Coffee Shop this morning, I like Coffee Shop." Or if you rode up on a bike I'd comment on that. Basically small talk but slightly more curious. If she never does this then she's really really shy or not interested. If she was that shy she wouldn't be working with people. In any case, don't ask her out at work.
posted by desjardins at 1:09 PM on June 1, 2011 [8 favorites]


I will be what seems to be the lone voice of dissent here. I get asked out at work here and there and it can be done with grace and decorem. Seriously.

First, you have to actually talk to her first. Get a laugh in, maybe shake her hand in and then leave. That is important. Do not ask her out the first time she is possibly recognizing you as a person not a faceless customer.

Second, when you see her wave, quick wave or a solid "dude nod", master it.

Lastly, after you have established some manner of rapport, I say go for it. It can totally be done without either party being weird or freaked out. If she at all blanches, back off immediately. Do not make it awkward and it doesn't have to be awkward. It should be fine.
posted by stormygrey at 1:10 PM on June 1, 2011 [1 favorite]


I don't think there's anything wrong with you, from what you describe about yourself. Asking someone out on a date is very difficult, so, first of all, give yourself a break about feeling nervous about it or worrying about rejection. I think maybe your first problem is just overthinking that you have a problem.

My advice here, though, would be that you probably shouldn't ask someone out at their job unless you get to know them a little bit. You say you go to the store somewhat regularly, so possibly you have a chance to exchange pleasantries with her. But I would be cautious about this, too.

I would only do this if I could do it so that my agenda isn't twisting my normal conversational choices. So don't laugh at her jokes if you don't think they're funny, don't interject compliments awkwardly. Be nice, be honest, try to get to know her slowly. If you end up on first-name basis with her, then you might have an opportunity to ask her to do something friendly at some point.
posted by Philemon at 1:11 PM on June 1, 2011


Agreeing with the posters above not to do this. I have done this, and a) it always ends up creepy and you feel even worse, no matter your intentions, and b) it never works anyway.

Be nice, be chatty if you want, and with any luck you can build a foundation with this person that's not at her work (and obviously don't get all stalkery about it).

Sorry. I know it's a tough spot.
posted by Capt. Renault at 1:12 PM on June 1, 2011


About your underlying issues, have you looked at whether you might suffer from some social anxiety? I know it's a trope on askme, but I went to therapy because I couldn't date (and never had, and was five years older than you). We did a lot of work on self esteem and social anxiety and I am a Much Happier person who is more social and happily in a romantic relationship.
posted by ldthomps at 1:12 PM on June 1, 2011 [1 favorite]


He knows nothing about me and so I'm basically interchangeable with any other woman he thinks is pretty; this is not flattering.

Ah, Frowner explained what I found creepy about your statement "I know nothing about this woman other than I find her attractive." What on earth are you going to talk about on your date, then?
posted by desjardins at 1:13 PM on June 1, 2011 [1 favorite]


@desjardins: What I meant by "I'm okay with that," is that, while shy and inexperienced, I'm not so naive as to think rejection doesn't happen. As in, I don't feel the need to know 100% for sure that if I ask, the answer will be a yes.

As for the other bit about me finding her attractive, I'm not entirely sure I follow; don't people sometimes ask each other out solely based on person A finding person B attractive in some way? I'm going to assume that not everyone who dates is dating someone they already know in some capacity, or is that way off base? (And I'm not at all being smart here, I'm dead serious.) In my mind, a first date is to get to know the person a little, no?

As to the answers that say, "Not at work!", alas, that's more or less what I was leaning toward. If I had ever seen this woman elsewhere, I wouldn't even be considering the idea, but I think she may very well have a teleportation device that hooks directly from her work to her home.

And @ldthomps, yeah, I've suffered from social anxiety, depression, etc. in the past, and it strikes me off and on still. I've gotten better, ironically, but I still have slumps.
posted by menschlich at 1:20 PM on June 1, 2011


I think the only way to do this is to get to know her a little better. However, attractive women who work in customer-facing positions often have to deal with guys trying to get to know them better and taking up their time while they need/want to get back to work. So be really careful not to over-do it.

This is what I would do if I were you. The next time you pick up a prescription from her say, "Hi! How ya doing?" and smile. If she asks how you're doing in return, tell her *one* positive thing about how you are doing, that can be said in no more than one sentence, "Having a great day, on my way to a baseball game this afternoon." She'll respond politely, but don't try to keep the conversation going. Just continue with your transaction as you normally would, and leave.

Do this again the next time you go in, exactly the same way. It needs to be up to her to make the conversation longer than it was the last time. When you ask how she's doing, if she gives you a reply that's longer than "fine, thank you!" like she actually tells you something about herself, e.g. "It's been a rough day today." you can respond to that, briefly. If you tell her your one sentence about something going on with you, and she replies with interest in talking a bit more -- and if she *asks a question* that's a sign that she's interested in talking a bit more, e.g., "Oh, what teams are you going to see?" then you can pleasantly make a ONE-SENTENCE reply to that question and smile.

Do it the same way the next time, just let the conversation get incrementally longer like that, following her lead.

If it doesn't get longer, like she gives you brief, impersonal, disinterested replies ("How are you?" "Fine, thanks.") then back off and just be a friendly customer.

Good luck.
posted by Ashley801 at 1:22 PM on June 1, 2011 [34 favorites]


Being at work means she can't get away from you and she has to be nice to you. Don't ask her out, the power balance is all screwed up and it's really not fair to her. Also, if you're finding excuses to pop in specifically to see her than that's creepy too. She's basically a captive audience, don't use that against her. I realise that this means you may only see her sporadically and never get the chance for anything more than a couple of sentences of small talk, if that, but that's how it goes. She's there to work, not to be picked up or to feed into your fantasy.

And fantasy is pretty much all you have by the way, you know nothing about her besides how she looks and whatever you've made up in your head ("I think she looks like she'd be interesting to get to know. Just a gut feeling, really."). There are plenty of other places to meet women where you can very quickly interact with them enough to take it beyond this stage, and where it's appropriate to ask them out if you actually click.
posted by shelleycat at 1:22 PM on June 1, 2011 [4 favorites]


//frankly, I hate being the way I am.// I almost missed that last line. Being social is a skill that just takes practice, like anything else. Basically, get out amongst people (join activities you're curious about or at least leave your house) and get to know people. Maybe focus on getting to know other guys first because it might be easier and it sounds like you want more friends anyway. If you want books, "Intimate Connections" by David Burns and "No More Mr. Nice Guy" by Robert Glover have some advice.
posted by sninctown at 1:25 PM on June 1, 2011


I think it's possible to ask someone out at work without it being overly awkward, but it could easily go wrong and would be a lot more likely to work out well if you had better social skills.

stormygrey describes an approach that *might* make asking her out non-awkward, if you were lucky, but I kind of feel like you don't have the skills needed to make that approach work. That's OK, and you're basically normal in lacking those skills, but you sound like you probably need to work on Social Skills 101 before you go on to this, which is more like Social Skills 382, Advanced Delicate Dating Situations.
posted by MadamM at 1:26 PM on June 1, 2011 [3 favorites]


As for the other bit about me finding her attractive, I'm not entirely sure I follow; don't people sometimes ask each other out solely based on person A finding person B attractive in some way? I'm going to assume that not everyone who dates is dating someone they already know in some capacity, or is that way off base? (And I'm not at all being smart here, I'm dead serious.) In my mind, a first date is to get to know the person a little, no?

Not in my world o' dates, no. There are lots and lots of physically attractive people in the world; I like a little bit of a heuristic before I start buying people flowers. Are we likely to have any interests in common? Are we likely to have profoundly incompatible lifestyles or worldviews? Are they really, really boring? What's more, I can't imagine wanting to go out with someone who wasn't interested in sussing this stuff out a bit in advance - their willingness to accommodate any social or ideological tendency of mine simply on the off chance of getting laid would say to me that we were not compatible - and would suggest that their view about women weren't too awesome.
posted by Frowner at 1:27 PM on June 1, 2011 [11 favorites]


Do you know her last name? Can you find her on Facebook? Of course it's possible to be creepy there, but it's a lot easier not do. The internet has made interactions like this a million times easier.

Send a friend request (assuming you have had conversations IRL). "Hey it's Joe from _____", if she accepts, great. if not, no big whoop.

If you become friends, there's kind of a natural progression of chatting, "liking" each other's stuff where you can get an idea if she might be interested without blurting it out. You may even organically realize you are going to the same social event.
posted by drjimmy11 at 1:28 PM on June 1, 2011


Work as in an office, or work as in a retail shop? Not that it makes a difference.

I really liked ashley801's approach. Strike up a conversation and get to know her. Nothing creepy there, unless you make it creepy.
posted by TheBones at 1:30 PM on June 1, 2011


After re-reading the question, I realize you have never really talked to her just to talk. You should do that a few times before looking for her online.
posted by drjimmy11 at 1:30 PM on June 1, 2011


Pharmacy, sorry.
posted by TheBones at 1:30 PM on June 1, 2011


Ooh, I'm going for the bonus points! Get some self-respect, man. You're looking at this woman like she's god's gift and thinking all the wonderous thoughts that are easy to think if you get desperate. What if she annoys the shit out of you? What if you can't stand her? Like desjardins said - you don't even know anything about her. What you've seen is her customer-facing self, which is not likely who she is.

You're desperate. Stop that, and have some self respect, and start acting like you are worth something. People are attracted to self confidence.

To stifle this urge to want to ask out Cinderella, list 15 things you hate - Microsoft, Crocs, people who call other people "champ", and imagine she does them all. She may very well just do that. If you're ultimately looking for someone to be with or hang around, you have to at least have some opening conception of who they are, or otherwise have something in common besides "you work here and I shop here". This isn't high school.

As far as the other stuff you want to do but don't - again, self confidence and self respect. You won't take risks? Are you afraid you'll get made fun of, for failing?

Think back to when you were married. Did you get hit on way more then, than you do now?
posted by cashman at 1:35 PM on June 1, 2011 [5 favorites]


Do you know her last name? Can you find her on Facebook? Of course it's possible to be creepy there, but it's a lot easier not do. The internet has made interactions like this a million times easier.

But if someone who was a stranger to me, who just saw me when I was at work, to whom I had never told my last name, tracked me down this way, I would be SUPER creeped out. I would just assume they were a creeper off the bat, fair or not. Years ago when I worked at a gym something like this happened to me but not even this stalkerish, the guy really did just happen across my profile though a few degrees of mutual friends, and I was still a little weirded out. Her mileage may vary, but just saying, I wouldn't risk this.
posted by Ashley801 at 1:35 PM on June 1, 2011 [14 favorites]


don't people sometimes ask each other out solely based on person A finding person B attractive in some way? I'm going to assume that not everyone who dates is dating someone they already know in some capacity, or is that way off base?

I don't know anyone who has successfully asked another person out in this way. All of the people I know who are in relationships had some chance to talk to the other person before they went on a date. Maybe they met online, maybe they chatted at a party, maybe they both volunteered at the same organization, etc. My stepsister was a waitress and got asked out multiple times a night for years. She never went out with a single one of those guys, and ended up marrying someone she worked with.

Don't believe the romantic movies, it doesn't work that way. If she drops something and you help her pick it up, you will not look longingly into each others eyes while music plays.
posted by desjardins at 1:37 PM on June 1, 2011 [2 favorites]


But if someone who was a stranger to me, who just saw me when I was at work, to whom I had never told my last name, tracked me down this way, I would be SUPER creeped out.

Yes, do not do this.

Also, keep in mind this woman may be in a relationship.
posted by cashman at 1:39 PM on June 1, 2011 [1 favorite]


Twice since starting my current job (so, in the last few months), I've had co-workers press the get-here-NOW button on the store system. On both occasions, the member of staff was female, and a male customer was trying to ask them out. Both times, I sent the staff member on their break (one of them had seniority over me) and dealt with the customer myself. On both occasions, the member off staff in question was creeped out by the customer.

Don't ask people out when you're in a position of power over them.

Regarding being shy, I hear you. It's tough. Try working retail sometime. It helped me cure my social phobias, which were strong enough that picking up the phone and calling for Chinese take away was a huge source of stress for me. Having to deal with lots of different types of people and make on the spot decisions will really help you get your chops together.

One thing that strikes me about your question is the aspect of it that's all about you - how you feel in social situations, how you feel about this individual. You don't seem very interested in how other people feel. Working on that will help you with your social skills.
posted by Solomon at 1:39 PM on June 1, 2011 [4 favorites]


@cashman: Yeah, I know, my self-respect / self confidence is extremely low. Not real sure on how to go about fixing that, though. I've read a bunch of threads on AskMe about the problems I have, and while the ideas within seem solid, they haven't really helped me much. I suck at faking it until I make it.

As for being hit on when I was married, I can honestly say that I don't think I was ever really hit on. I live in a fairly small town (less than 20K people), and there's not much to do unless you're into A) bars or B) churches. Neither do much for me. As such, I'm the world's biggest homebody. I don't like it, but barring just going outside and sitting for the hell of it, I don't know what to do. And, when I do occasionally find myself at social things, as noted above, I'm a pro at making myself be invisible.
posted by menschlich at 1:40 PM on June 1, 2011


I don't know anyone who has successfully asked another person out in this way.

Seriously, join some groups - you're young enough that the age-appropriate dating pool in a political/arts/social/sports organization will be big, plus you'll get invited to parties. And at those parties, you can meet people! Even I, introverted, neurotic and funny-looking as I am, met people and got dates via volunteering and party-attendance. Plus, when you first join a group, you are the new person and you have a dating advantage. And you'll get to do lots of low-stakes social things...you can go to a party or an event for an hour, chat to people, and leave when you feel like you've had enough.
posted by Frowner at 1:42 PM on June 1, 2011 [1 favorite]


I live in a fairly small town (less than 20K people), and there's not much to do unless you're into A) bars or B) churches. Neither do much for me.

Move.
posted by desjardins at 1:43 PM on June 1, 2011 [10 favorites]


I think you need to work on your self-image a bit before asking anybody out. You've got to like yourself before you can expect anybody else to like you. And dude, unless your marriage was the result of an all night bender in Vegas, after which you woke up married, you have far more social skills than you give yourself credit for. Your marriage lasted 5 years, you have a child. Those are not insignificant things. Plus she loved you enough to say yes when you proposed. Not a small thing at all.

Buck up, find a meetup that interests you, and for the next six months just focus on making some friends. Once you have that down, the whole asking out on a date thing will seem much easier. But you still shouldn't ask the pharmacy tech at the counter. That's going to be creepy just about anyway you play it.
posted by COD at 1:44 PM on June 1, 2011


Ooh, sorry about the small town thing. What about OkCupid, etc? You could be a charming internet correspondent, perhaps?

You're almost certainly more interesting and visible than you think, too. You've probably been hit on and didn't realize it - it took me into my thirties to recognize when someone found me attractive. Alternatively, you may be too interesting for your town - what is keeping you there? Can you live elsewhere and commute?
posted by Frowner at 1:46 PM on June 1, 2011 [2 favorites]


She needs to know whether she wants to go out with you. As it is right now, she can't know that. She doesn't know if you are nice and normal or potentially dangerous. If you ask her out cold, I almost guarantee you a "no."

Does she know your name? Have you introduced yourself? Chatted a little when she wasn't too busy?

When I worked in a library, I was constantly getting asked out cold by men I'd never met, and whose names I did not know. Seriously, it was frightening. You've got to give her a chance to see you as a nice, non-threatening person, and hopefully one she thinks she might be compatible with.

As for the attraction thing? For women (if everyone will permit me a generalization), they can often be more attracted to a man after talking with him, rather than feeling an immediate yes! or no!, you know? So it's unlikely that she would think, "Cute stranger, I would totally go out with him right this minute." But give her a chance to develop a little interest in you, and she might be more likely to say yes to a date.
posted by Knowyournuts at 1:46 PM on June 1, 2011 [1 favorite]


Wait a minute, now. Since you say you live in a tiny town, I think that changes the dynamic about asking her out at work somewhat.

Although this fact makes it hard for me to understand how there are always "10 people buzzing around her," unless the pharmacy has become a kind of hang-out in a town where there's just not much to do (as you describe it).
posted by Philemon at 1:50 PM on June 1, 2011


Don't ask people out when you're in a position of power over them.

Repeated for truth.

Please don't mistake her professional courtesy as genuine interest.
posted by Capt. Renault at 1:50 PM on June 1, 2011 [3 favorites]


Philemon: the 10 people I referred to are other workers. Behind the counter it's fairly open except for pill shelves and the other employees are always fairly close.
posted by menschlich at 1:55 PM on June 1, 2011


i've had some guys ask me out at work. i've always said no. once i said no and that guy was waiting out back where the employees exit, at 10pm, in an empty mall parking lot. he was just waiting to ask again. but i was spooked for months. i got escorted to my car every night by security. i begged off of early opens and late closes that i had to do alone. i was less friendly to the men who came in. i was petrified the next time a customer asked me out.

while some women won't mind, a lot of us will. it's hard to put yourself in the shoes of the opposite sex, but you should try in this case.

attractive, youngish women are basically constantly bombarded with sexualized attention they aren't seeking. if they aren't super bubbly they get told to smile, to cheer up. if they dared wear something fitting, they get comments about how good they look all day. they get reduced to a single body part by guys trying not to be creepy - "i like your hair, your smile, your eyes, your teeth, your shoes." somewhere guys got the dating tip that this was a good substitute for complimenting a woman's ass, tits, legs (while not as bad, it's still not good).

when all of these things happen, day in and day out at work - a woman has to learn how to just take it, to smile back, to flirt a little (if she depends on repeat business). this is not a level playing field. this isn't fair to the woman you supposedly like enough to ask out.

i don't say any of this to hurt your feelings or widen the gap of lonliness that you're feeling. it sucks to be socially anxious (i am). it sucks to feel invisible (i've been there). however, none of the feelings excuse glossing over steps in the social process. you have to do the hard stuff - online dating, clubs, volunteering, working on your self-esteem to get the results you want. this isn't the only woman in the world who will smile at you even if it seems like it right now.
posted by nadawi at 2:02 PM on June 1, 2011 [19 favorites]


I think Ashley801 provides the best advice for reaching the specific goal of starting a relationship with that girl.

If that doesn't work then realistically I think you either need to become less of a wall flower or move to a bigger area where you have a better chance of finding activities that do interest you. I totally sympathize with you as I think we have very similar personalities and, while larger, Davenport, IA doesn't really offer much that interests me.

Good luck.
posted by Green With You at 2:04 PM on June 1, 2011


Ah, thanks for the clarification.

You're right -- it would be tough to get a private conversation going with her. But this set-up also presents an opportunity, where you can chat up her co-workers, too. In my experience, women find attractive guys who are friendly and social, not just with them, but demonstrably with others.

You might consider being friendly and chatty with anyone who happens to provide customer service for you there. As her colleagues get to know your name and face, they may chat about you when you leave, etc. Let people near her get to know you, get to know your interests, and you'll be on the road to creating relationships in the pharmacy. Which, who knows?, could lead to something.

And by the way, you say you live in a 20K town with churches and bars and not much else. I'm thinking that, unless this is a college town or pretty near a big city, that the number of date-able eligible men under 50 around you is in the single digits. You seem like a smart, decent guy with good self-awareness about your foibles, so buck up a little, take it slow, take Ashley801's good advice, and see what happens.
posted by Philemon at 2:05 PM on June 1, 2011


As a friend once put, most indelicately, you need to be 100% certain before asking the help out.

I've always stayed with that policy, despite strongly feeling interest from the occasional waitress at a regular place.

See the Onion for more.
posted by Ironmouth at 2:09 PM on June 1, 2011


Here is how it worked for me:

I talked to the local girl at the pet store for a year before I finally worked up to asking her out. I remember getting the idea that she liked me when she once asked "So how was that trip to St. Louis?" and I was all... "Uh, what?" in a decidedly not smooth manner. Then I remembered telling her that's where I was headed 3 or so months ago, and I hadn't seen her in my infrequent pet food buying trips for awhile.

Turns out she and I had been crushing on each other for a year, but I was still super hesitant. If you're not striking up really long conversations, don't ask her out. A tentative chit-chat question could be "Up to anything exciting this weekend?" and if she goes into details, that is a (possible maybe) good sign. If it's a very short answer, I'd not bother keeping the idea alive.
posted by OnTheLastCastle at 2:22 PM on June 1, 2011 [2 favorites]


in my late teens/early twenties, I worked as a cocktail server in various places, and was asked out quite often. interactions ranged from nice regulars with whom I'd conversed on multiple occasions, to the guy who asked me out while his pen was hovering above the tip field of his bill. I SWEAR TO GOD.*

I had a boyfriend all those years, so I never said yes. but -- Ashley801's suggestion might have worked, if I were single, and you truly seemed like a nice guy. the key is no pressure, no guilt, and be sensitive to her signals. take it slow, and her responses at face value. any time I was ever creeped out by somebody's advances, it wasn't because they were asking me out at work, exactly -- it was because they were being creepy about it: aggressive, vaguely pervy, or entitled. or they were twice my age.

*needless to say, he gave me a shitty tip.
posted by changeling at 2:26 PM on June 1, 2011 [2 favorites]


As for the other bit about me finding her attractive, I'm not entirely sure I follow; don't people sometimes ask each other out solely based on person A finding person B attractive in some way? I'm going to assume that not everyone who dates is dating someone they already know in some capacity, or is that way off base? (And I'm not at all being smart here, I'm dead serious.) In my mind, a first date is to get to know the person a little, no?

I'm sure in some cases people ask others out based solely on physical attractiveness, although I'm not personally familiar with any situations like that. But if you're going to ask someone out based solely on her being physically attractive, rather than at least some minimal rapport and connection and interest based on interaction (which doesn't have to be deep and extensive, but should give you a very basic sense of being attracted to eachothers' personalities-- on a superficial level, but it's a start, and then on the first date you can start to find out if that superficial attraction goes any deeper-- rather than just sending the message "I think you're physically attractive, I'm only attracted to you because of what you look like, having nothing to do with who you are as a person")... then at least have the decency to do it in a situation where the person is reasonably likely to be open to the request (i.e. at a bar.) Combining "I'm asking you out purely based on physical attraction" with "I'm asking you out at your workplace where you are constrained to be polite to me, at the risk of you feeling uncomfortable from here on out at your place of employment," both of which are pretty questionable on their own, seems like a bad, bad, bad combination.

If you're really set on this woman (not sure how you could be since you don't know a thing about her, but whatever), then follow Ashley801's advice and try to get to know her just a little bit first and see if she likes you a little too. But really, if you just picked her because she's pretty, isn't there anyone else pretty in your town you could find to ask in better circumstances? Why her?
posted by EmilyClimbs at 2:33 PM on June 1, 2011


Do you know what? Life is too short to put this kind of thing off.

My friend once told me the story of how his parents first met, which was the same situation, only the woman was a supermarket cashier. One day, my friend's father decided to ask her out. They are still married.

By the time he asked her out though, it's clear that they had some kind of rapport going on. So make sure you do a good job of following Ashley801's advice. If you can't get some rapport started, give it up and move on.
posted by Juso No Thankyou at 3:00 PM on June 1, 2011


Yeah, don't do the Facebook thing. I'd find it weird. I deal with people on the phone a lot in my job, and sometimes I think we;d get on if we met in person (I'm taken, so I mean more in a friendly way!) but I'd still find it a bit inappropriate to look them up on Facebook and make friends with them. If I didn't really know them at all, it would be super weird.
posted by mippy at 3:11 PM on June 1, 2011


It's totally your prerogative to ask any girl out. You're not responsible for her feelings about that. Having said that, the odds are against you, but that's just the nature of the random date request.

As for your underlying issue... social anxiety? too obvious?
posted by mpls2 at 3:15 PM on June 1, 2011


@mpls2: Yeah, social anxiety, occasional depression, shyness, etc. I've not had much luck in fixing these problems, though.

After reading everyone's answers, I think, at base, my question doesn't really have much to do with this girl. I mean, it does - I do think she's cute and wish I could get to know her - but really, the real, imporant issue is the underlying stuff. How to deal with people, how to make friends, how to ask people out, when to do it (and when not to), and so on. I was depressed all through high school, and it seems I'm still lagging behind terribly when it comes to this stuff. My desire to ask this girl out is, I think, more a desperate grab towards normalcy: I want to feel like I belong in the big flock of humanity, and a lot of time, I don't.

I'm a lovely bag of issues. :\
posted by menschlich at 3:20 PM on June 1, 2011


my question doesn't really have much to do with this girl.
I was going to say the same thing but you beat me to it! I think seeing her, thinking she's pretty, and thinking about asking her out, etc. is waking something inside you. Obviously your next step is not to ask her out, but to think about what's waking up inside you and explore it with compassion for yourself. I think the stuff you have to deal with is even more underlying: believing that you're a worthy person deserving of friendship, kindness, respect, love. You may find this book helpful. You've got at least one thing (and you have lots, I'm sure) going for you: a good sense of self-awareness. This will definitely serve you well on your journey.
posted by foxjacket at 3:32 PM on June 1, 2011


Step the First: quit insulting yourself. You are not "a lovely bag of issues". You are a human being who hasn't leaned some life skills because he was (and quite possibly is) unwell. Depression is an illness.

Step The Second: treat that illness. Get yourself to a doctor and get yourself checked out.

Step The Third: start working on your social anxieties. I do two things; organise the party (so everyone there will be someone I know and have something in common with) and make people laugh (people will love you forever if you make them feel good). Start small, and invite a couple of friends out for coffee or something. And show an interest in them. Most people love talking about themselves, especially if they're sharing gossip or the experience is cathartic in some way, such as moaning about work. Make lots of eye contact and nod sympathetically. Lather, rinse, repeat.

I've had to struggle with the exact same things. I managed and am a human being, so you, being a human being, can probably manage too. If it's any comfort, lots of people struggle with these skills. Regarding asking people out, discernment comes with experience. You're trying to run a marathon when you can barely stagger. Take baby steps.

Memail if you want to chat.
posted by Solomon at 3:35 PM on June 1, 2011 [5 favorites]


I think this can be done, but, like some other posters have said, you need to work up to it. I also don't think your goal should be eventually asking her out, because that will probably come across to her. Whenever a man speaks to me and I know it's just because he wants to have sex with me or ask me out or whatever, I'm bored and annoyed from the first utterance, pretty much without exception. You must be genuinely interested in getting to know her. After awhile, if you still want to after learning about her, AND the opportunity naturally presents itself, go for it.

The drawback to this is it will be awkward in future interactions. So what? It'll be awkward for you at any rate because you always wanted to ask but didn't. Plus, if you have become semi-friendly with her, she should forgive you for asking even if she is not interested. If she doesn't and it becomes a little weird, again, who cares? Your interactions will be pretty brief and a few minutes of feeling awkward is not the end of the world. Expressing an interest and attractions to someone that is not returned is likewise not the most embarrassing, end-of-the-world thing, and if she acts like it, then she is really silly.

Honestly, to me, though, it sounds like you need to work on your own thing a little bit before you go dating. This doesn't mean you can't talk to her, like I said. You can & should. But being in a good relationship requires a healthy view of yourself, and I don't think you are there.
posted by amodelcitizen at 3:46 PM on June 1, 2011


I'm starting to feel like this is a little bit of a pile-on, but pretty much every service industry job I've ever had (restaurant, retail store, library) has at some point involved providing cover for an employee who was receiving unwanted asking-out-type attention from a patron. Seriously, every job, probably dozens of different suitors. If you haven't spent time working in that kind of environment, especially as/with a woman, you probably have no idea how common it is, and how fraught a situation it can be for the person you're asking out. Please, please, please just meet some people who aren't in a customer service role to ask out.
posted by pullayup at 4:04 PM on June 1, 2011


i'll nth the advice about at doing a fuck of a lot of chit-chat first -- you know, the kind of thing you'd do prior to asking anyone out in a non-work environment. don't ask her out cold.

however, i'll provide a counterargument to the "dudes who ask girls out at work might be creeps" worry, and that counterargument is this: everyone might be a creep.

so, unless she works at a job which serves a higher percentage of creeps than normal -- does a pharmacy really fall in this category? -- it doesn't seem any more likely that the guy asking her out at work will be a creep than if that same guy asks her out at a bar, or at school, or at a library, or at a coffeeshop.

if people never asked each other out when there was a non-zero possibility of the other being worried about potential creepiness, the concept of dating would not exist.

now, lots of people have these worries, and lots of these worries are justified, but the majority of people aren't creeps. for this reason, it makes no sense (imho) to have a blanket rejection policy based on this possiblity. neither does it make sense to have a blanket no-asking policy based on this possibliity. all this shit is more context-sensitive than blanket policies let on.
posted by matlock expressway at 4:39 PM on June 1, 2011 [1 favorite]


all that said, it's a good general policy to avoid asking people out at work. but when the situation is "holy fuck, this girl is sending me all possible signals aside from asking me out directly", a smart thing to do is to ask the girl out, rather than deferring to some absolute prohibitions against it.

unfortunately, nothing in what you said indicates that this is one of these situations.
posted by matlock expressway at 4:42 PM on June 1, 2011


Thanks for all of the input, folks. I'll be glad to accept any more tips, etc. regarding ways to deal with my underlying issues, but just for the record, I do see why asking her out at work is a bad idea, for all sorts of reasons, and I won't be pursuing the idea any further.
posted by menschlich at 5:07 PM on June 1, 2011 [3 favorites]


so, unless she works at a job which serves a higher percentage of creeps than normal -- does a pharmacy really fall in this category? -- it doesn't seem any more likely that the guy asking her out at work will be a creep than if that same guy asks her out at a bar, or at school, or at a library, or at a coffeeshop.

Oh, but it does! There is one thing you know about a stranger who asks you out at work that you don't know about a stranger who asks you out in public somewhere: this guy either doesn't care or doesn't get (for reasons that might not be complimentary) that he is asking out somebody who can't go anywhere, has to be nice to him, and will have to be nice to him again in the future anytime he wants to show up there.
posted by Adventurer at 5:30 PM on June 1, 2011 [1 favorite]


(foxjacket, I'm afraid your link didn't work.)
posted by moira at 5:39 PM on June 1, 2011


if people never asked each other out when there was a non-zero possibility of the other being worried about potential creepiness, the concept of dating would not exist [...] it makes no sense (imho) to have a blanket rejection policy based on this possiblity. neither does it make sense to have a blanket no-asking policy based on this possibliity.

See, but the difference is that people often go to bars, or join okcupid, etc. with the express intention of being asked out, or of at least talking to people in a might-be-interested-in-dating way. This woman is at the pharmacy to earn money, and it's not safe to assume that she's interested in being asked out, especially because her job requires her to interact with this guy in a cordial fashion. She might happily say "yes," of course--nobody is suggesting that she should reject anyone who asks her out at work as a matter of principle--but it is still a dick move to ask her out with no prompting. This is because she cannot know if he is going to be a creep, or dangerous, and anyway, couldn't respond appropriately if he was (in extreme cases, she might even be putting her job at risk). This is, I think, a hard point for men trying to understand this situation to grasp, because romantic attention from women, while possibly unwelcome, is rarely a prelude to inappropriate or threatening behavior.
posted by pullayup at 5:52 PM on June 1, 2011 [2 favorites]


Oh, but it does

duly noted. i see the point completely.

it is still a dick move to ask her out with no prompting.

uh, yeah, i said pretty much that: i.e., that one should only ask someone out after a 'fuck of a lot of chit-chat first' and only where there is unmistakable flirting going on.

of course, not everyone can differentiate between (a) the perfunctory 'getting paid to be nice with you' sense of interpersonal interaction and (b) flirting. but geez. some people can.

that said, i've never asked out a girl at work -- until now because it seemed really hokey; after this discussion, though, i'll probably avoid it due to being viewed as a total creep-o.
posted by matlock expressway at 6:08 PM on June 1, 2011


I'm the world's biggest homebody. I don't like it, but barring just going outside and sitting for the hell of it, I don't know what to do. And, when I do occasionally find myself at social things, as noted above, I'm a pro at making myself be invisible.

Have you considered volunteering with your child's school? If your child is too young for school or doesn't live in your town, you might try volunteering at the local school anyway. It's structured social interaction which is what I think will be easier for you to start with. Your help will be very highly appreciated. And you will meet women, lots of women.
posted by Ashley801 at 6:26 PM on June 1, 2011


OP - don't be too hard on yourself. You sound like a decent guy, you probably just need a little confidence boost.

One thing that strikes me about your question is the aspect of it that's all about you - how you feel in social situations, how you feel about this individual. You don't seem very interested in how other people feel. Working on that will help you with your social skills.

This, a thousand times this. I used to have some of the same problems you described when it comes to socializing (still do from time to time) and just adjusting the focus from thinking about myself to thinking about other people made a huge difference. My suggestion would be to concentrate on that for now - learn how to be comfortable in social situations, get practice and friends will come naturally. Some of the suggestions listed above (Meetup, volunteering, etc) are good places to start.
posted by photo guy at 6:35 PM on June 1, 2011


how do I go about getting over my stupid hang-ups and ask a complete stranger out, while she's at work?

You do not.

If and only if, through your normal, professional daily interactions, you build up enough of a rapport through your wit or charm or politeness or common interest that the person asks you out, can this ever happen. But the important point is that the ball is in their court, not yours.

Bonus points if you can help me figure out what my underlying issues are, because frankly, I hate being the way I am.

You are shy. Talk to people more. Go out someplace, bring the crossword puzzle from today's paper, order a pint of something beery and sit and wait. Listen to people. Hear not only what they're saying, but how they're saying it. Are they being loud or talking quietly? If they're talking loud, and it's about something that interests you or intrigues you or you think you know something interesting about, then you wait patiently for your opportunity. You listen to what they say, nod when in agreement, but do not make eye contact yet because you are not invited yet into the conversation. Wait. When silence comes, look them in the eye, speak up and speak clearly and say what you have to say, and let the chips fall where they may, and if that person is a kindred spirit, someone that you might someday call your friend, well that person will listen to you, and will respond, and you will be having a conversation. And if that person is an asshole, someone you wouldn't want to be friends with, well, they'll let you know straight off. Thank them (silently, to yourself) for saving you a whole mess of time.

That's how you do it.
posted by Civil_Disobedient at 6:43 PM on June 1, 2011 [4 favorites]


uh, yeah, i said pretty much that: i.e., that one should only ask someone out after a 'fuck of a lot of chit-chat first' and only where there is unmistakable flirting going on.

I'd like to apologize for getting a little het up about this--we're pretty much on the same page and I cherrypicked bits of what you wrote to frame my point, even though the post as a whole had a different, and more conciliatory, tone.
posted by pullayup at 6:49 PM on June 1, 2011 [1 favorite]


One of my best friends is a bartender in Brooklyn. She is asked out very often by regulars at the bar. The one thing she hates more than anything else? After she turns them down politely and without judgement- They NEVER come back. Ever. It sucks because she loses that customer AND it makes things awkward whenever she sees them in the area. SO if you do decide to do it, don't be mr. dissapearing guy.

That being said- She's actually dating (for three years now) someone she met when she was serving him drinks. He was polite, nice and attractive- and she threw about seventy million hints at him to ask her out before he was sure enough to break the rules.

As soon as she is interested enough in you to break the rules and risk all the complications and awkwardness- she will most likely send you hints the size of a frieght train. Be friendly and wait for those, kiddo.
posted by Blisterlips at 6:58 PM on June 1, 2011


After reading everyone's answers, I think, at base, my question doesn't really have much to do with this girl. I mean, it does - I do think she's cute and wish I could get to know her - but really, the real, imporant issue is the underlying stuff. How to deal with people, how to make friends, how to ask people out, when to do it (and when not to), and so on. I was depressed all through high school, and it seems I'm still lagging behind terribly when it comes to this stuff. My desire to ask this girl out is, I think, more a desperate grab towards normalcy: I want to feel like I belong in the big flock of humanity, and a lot of time, I don't.

Two books I'd recommend are (Regardless of What You Were Taught to Believe) There Is Nothing Wrong with You: Going Beyond Self-Hate and Be the Person You Want to Find: Relationship and Self-Discovery, both by American Zen teacher Cheri Huber. I've been struggling with depression since before junior high (so, 30+ years now) and Cheri's books and other work have been life-changing for me. If her work clicks for you (not everybody likes it; like a lot of Zen, it can seem deceptively simplistic) I think you might find it helpful.
posted by Lexica at 7:32 PM on June 1, 2011 [4 favorites]


@Lexica: Thanks for the book titles. Strangely enough, I just grabbed a "Daily Zen" app for my phone yesterday produced by Cheri Huber. I'll certainly take a look at them.
posted by menschlich at 7:55 PM on June 1, 2011


You've been quiet and a loner for most of your life. Why? Because you're afraid of getting your ass kicked, embarassed, whatever, I don't know what exactly it is, but you're scared of interacting. Stop being afraid. Its hard, trust me, I know. Everybody here is telling awful stories of how they had to rush in because a guy was bothering a girl they were working with. You probably have images of getting thrown out of your favorite pharmacy by burly bouncer-types, banned forever, never to return again, rode out of town on a rail by the citizens. Stop. This is exactly what you do next time you see her. Ask her what her name is. Say "Hi [Name], my name is [Me]. I think you're cute. Do you want to go out on a date with me?" When she says yes, you say "great, what's your phone number? I'll pick you up [three days from now] at 8." If she says no, say "ok, see ya around!" Next time you see her, say "Hi [Name]!" wave and go about your business. Don't be paranoid or afraid. Just don't be scared, or else nothing will ever be different for you.
posted by wayofthedodo at 8:21 PM on June 1, 2011


i forgot to add, repeat above interaction pattern for other people you want to ask out, if you have the inclination. replace cute with funny, interesting, or crazy as necessary for variety.
posted by wayofthedodo at 8:25 PM on June 1, 2011


What you need to be doing is building up rapport as Ashley801 says, but not just with this woman, with as many people as possible. Like, say, talking to 4 strangers a week.

Then when you go out in the evenings in your small town, the chances of running into someone you already know a bit are increased. You might run into this woman in your travels. Maybe you could ask her out then! You know, while she's not at work.

Does this sound like a chore? It is. However, it tends to work. Can't spring clean without rolling up your sleeves and getting dirty, right?
posted by tel3path at 2:50 PM on June 2, 2011 [2 favorites]


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