Bourbon at 8AM probably isn't the best solution

July 14, 2010 12:30 PM

There's a girl I see often that I'd like to get to know better. Problem: I'm absolutely terrified on how to start.

I've started to take an interest in this girl that works at a coffee house that I tend to stop by on the way to work in the morning. She's usually sitting in the corner alone eating breakfast and reading around when I get there. She knows my name from being there so often, but that's about it. Being an introvert (as well as being fresh out of a relationship that broke down over communication issues), I'm having a very hard time bringing myself to make any sort of advance out of fear of a backfire. I don't really know what to say, and I don't know how to psyche myself into actually going through with it.

posted by ConstantineXVI to human relations (27 answers total)

I was never good at making the first move, particular with a stranger, so I'll save that response for somebody with more experience. But I will ask if you know she's single. Make sure there's no ring on her finger before you open your mouth; it's not foolproof, of course, but that visual is a good way to avoid a really embarrassing situation that you might have neglected to consider on account of the butterflies.
posted by The Winsome Parker Lewis at 12:35 PM on July 14, 2010 [1 favorite]

You are worried about backfire, but not asking is the same as getting rejected. You are no worse off if you ask. I might start with a "Mind if I join you" when she is eating.
posted by JohnnyGunn at 12:38 PM on July 14, 2010 [1 favorite]

I should mention I wasn't intending on going into full-blown romantics out of the gate, to avoid total embarrassment like The Winsome Parker Lewis mentioned.
posted by ConstantineXVI at 12:41 PM on July 14, 2010

ask her what she's reading? it's a good way to get the "i'm interested in you" vibe across.
posted by angrycat at 12:41 PM on July 14, 2010 [1 favorite]

If she's reading while eating, I would absolutely not ask to join her. When I'm reading and eating by myself, that means I want to be left alone, and someone who tried to interrupt me would get a very black mark in my book. Especially if I were reading and eating right before I had to work.

It isn't clear if you've even said 'hi' to this girl. If you go there so often and she's always there, I would start with that. See if you can catch her eye, give a smile and a friendly 'Good morning'. See if she reciprocates, or says 'bye' when you leave.

Even though she isn't your barista directly, she's still in an awkward position of potentially having to be nice to you because you frequent her place of work. I would go very, very slow and read her signals.
posted by Phire at 12:45 PM on July 14, 2010 [6 favorites]

Please don't ask her what's she's reading. That is so annoying and likely to start you off on the wrong foot!

But maybe just something simple: hey we run into each other here all the time; would you be interested in getting together somewhere else sometime? maybe a movie?
posted by Eicats at 12:47 PM on July 14, 2010

Exactly what Phire said. Has she given any indication that she's at all interested? I don't really know how else to say this: Just because a woman is in public, it doesn't mean she's available or even wants to be approached. She may just be enjoying the only alone time she gets all day. And certainly don't ask her what she's reading.

Does she smile at you, ever say "hey"? Or is her nose always in the book?
posted by runningwithscissors at 12:53 PM on July 14, 2010 [2 favorites]

Alas. The barista rule: don't ask out baristas. (See also: the bartender rule, the waiter rule, et cetera.)

It's where she works.
posted by rafter at 12:54 PM on July 14, 2010 [3 favorites]

A) take note of what she's reading, without asking her and having her notice that you're looking at it.
B) read the book yourself
C) casually ask her what she's reading, the next time you're there
D) mention, "Oh, I actually read that not long ago. I thought it was interesting/cool/whatevs in (way x)."

You can make your next move (which may indeed mean: NO MOVE AT ALL) based on how interested she seems in talking to you about the book. If she seems polite but not really enthused, ABORT
posted by Greg Nog at 12:58 PM on July 14, 2010

The current extent of our interactions:

* I've been going by the place for a little over a year now, and she's been there about as long (as far as I know, the place isn't much more than 3 yrs old)

* If she's working when I come in, she'll usually say "Hi, ConstantineXVI", even if she's not at the counter. My response varies, depending on how awake I am at the time (I walk to work and the place is about 2 miles into my route, a little exhausting), but it's never much more than a hi back. If it's just being professional, she's doing a pretty good job of hiding it (I work a similar job); and I've never noticed her calling anyone else by name on a regular basis.

* If she's not working, she's eating and either reading or (occasionally) talking to a (female) friend.
posted by ConstantineXVI at 1:06 PM on July 14, 2010

That seems a bit more promising. Next time she says hi, you could ask something like "Hey, did you finish that book you were reading the other day? You seemed pretty into it."

And then see how enthusiastic she is about responding and about engaging in a conversation with you. The same pitfalls about the barista rule (etc) still applies, but at least you're not starting completely blind.

You could try maybe leaving the house 10 minutes earlier so you're not in-and-out in a hurry every morning?
posted by Phire at 1:12 PM on July 14, 2010

As a conversation starter, you can always ask her advice about something. Just make it something that you actually need help with or a second opinion. Perhaps a question based on your similar jobs?

In any case, you've been warned many times above about the perils of asking out a service employee in their place of employment. Tread carefully.
posted by mmascolino at 1:15 PM on July 14, 2010

Build up your conversations with her. Move from your "Hi", to "Hi, how are you doing today?". She will respond. One day, maybe even that very day she will even ask you how you are and you can respond. You are great, by the way. Not tired, not under the weather. You are great. Looking forward to the day/week being over. You can't wait for the weekend. She might ask why or she might agree with you. One day she'll ask what you're doing. You're doing something very cool. She might like to join you at it.
posted by IanMorr at 1:17 PM on July 14, 2010 [14 favorites]

Take note of what she's reading, and start carrying around a book by the same author or something notable in the same genre. Without trying too hard, see if you can get her to notice it. Then you can say something intellectually stimulating, or make a pop culture reference, or have a joke (but be careful), or best of all, compliment her taste in literature. Try to lead the conversation into "have you seen so-and-so current movie/cultural event/etc?" and then invite her to attend with you. This will take some thought and should maybe be accomplished over multiple days. Good luck!
posted by funfetti at 1:23 PM on July 14, 2010

I think finding out what she's reading and then manufacturing a fake interest in that author or book is deceptive and creepy. Of all the responses on here, I like IanMorr's the best. It's effective but natural and doesn't give stalker vibes.
posted by The Winsome Parker Lewis at 1:29 PM on July 14, 2010 [5 favorites]

I can tell you that the odds don't favor you if you've been going there for more than a year and all she does is smile and greet you by name when she's on-shift. If she sees you coming in when she's not working, and makes no particular effort to talk to you, then she's either a huge introvert - this is possible! - or more likely, she's not interested. No big loss. It's a big world out there.

Your best bet is to approach while doing something else - walking past her to throw away trash or something, you'll figure it out - ask her a quick question about the book she's reading - is she liking it, maybe you read it too and want to know what else is good by that author, you get the idea - something brief. Be apologetic for interrupting her; the ideal approach here is to be self-effacing, which is not the same as self-deprecating. If she answers the question politely and then goes back to the book, then you should smile, thank her, and then leave her alone. I am not one to rain on parades, but this is the outcome you may want to prepare for ahead of time.

If she turns out to be into you but just shy then you will know it, and conversation will happen more or less organically, and you will not need to prepare for that ahead of time.

Your stint on this ridiculous ball of dirt and air and water lasts for a limited time, and you only get one. At the end of it I can promise that the chances you didn't take will bother you infinitely more than any you ever did. The above plan is more or less foolproof in that it requires no special amount of nerve and allows you to eject safely if it doesn't look to be happening. Go for it, and good luck.
posted by FAMOUS MONSTER at 1:32 PM on July 14, 2010

Oh, and two addenda:

1. The thing you ask about the book should be genuine. Don't say you've read something else by that author if you haven't. Figure out something you really do want to know and then ask it.

2. The above will only allow you to gauge whether you should continue with this business of maybe takin' her out for a highball and a steak dinner, or whatever a date looks like to you. The actual asking out is up to you, but I think you'll find it to be less stressful, and involve much less guesswork, once you're on firm ground. But if you're stuck for ideas: "Hey, I gotta run, but [movie] is playing and I was gonna check it out. You should totally go too, it looks fun." Be casual, be relaxed. At this juncture she will suggest going together if she thinks of you that way, or she will suggest going as a group which could go either way, or say no which speaks for itself.

Again I say, good luck.
posted by FAMOUS MONSTER at 1:40 PM on July 14, 2010

I can tell you that the odds don't favor you if you've been going there for more than a year and all she does is smile and greet you by name when she's on-shift. If she sees you coming in when she's not working, and makes no particular effort to talk to you, then she's either a huge introvert - this is possible! - or more likely, she's not interested.

Not necessarily, I don't consider myself a huge introvert, and I generally wait for the guy to make the first move (such a bad feminist!).
posted by ellieBOA at 2:06 PM on July 14, 2010

If a girl is interested in you, she will let you know by looking at you, smiling at you, talking with you, basically anything but completely ignoring you. If you're only getting the "completely ignoring" part, you already know the answer.
posted by Civil_Disobedient at 3:32 PM on July 14, 2010

If a girl is interested in you, she will let you know by looking at you, smiling at you, talking with you, basically anything but completely ignoring you. If you're only getting the "completely ignoring" part, you already know the answer.

Except that she hardly knows the poster (or she doesn't naturally approach customers or she is shy or in the past she had a relationship or etc.) I think the poster needs to step up and casually engage her in conversation. It is with only those reactions can he judge if he has a shot.
posted by mmascolino at 3:50 PM on July 14, 2010 [1 favorite]

Is there a local event that is public/free? Maybe a book/poetry reading?

"Hey, did you know that Author X will be in town? I'm going to the reading tomorrow. Maybe I'll see you there?"

Then never mention it again.

If you don't, maybe try one more time in a month or so. Then drop it.
posted by internet fraud detective squad, station number 9 at 4:04 PM on July 14, 2010

The way I psyche myself up for these sorts of things is to think of what I call The Me Of Tomorrow.

The Me Of Tomorrow will be really annoyed I didn't take that opportunity to say Hello, ask a casual question, see if theres any interest. The Me Of Tomorrow will realise that, without making that move, I'm in the same situation I'm in now, and that its really a no lose situation, she's not interested, then I'm in the same boat I'm in now except that at least now I know where I stand.

Don't do it for you. Do it for the You Of Tomorrow. He's worth it.
posted by Admira at 4:49 PM on July 14, 2010

I've posted this here before, but it is relevant here: "Nobody Ever Died of Awkward".

Eicats, way up at the beginning of the thread, had a great, low-key way to approach this. If she says no, move on and feel good that you braved the rejection. Don't let it stop you from going back to the coffee shop! If she gets weird afterward, then she's the one with issues.
posted by LOLAttorney2009 at 5:13 PM on July 14, 2010

If a girl is interested in you, she will let you know by looking at you, smiling at you, talking with you, basically anything but completely ignoring you. If you're only getting the "completely ignoring" part, you already know the answer.

This is not universally true. At all. Especially first thing in the morning, for pete's sake!

I think IanMorr has the most reasonable advice to just naturally lengthen your interactions and see what happens. However, if I were you I would totally do what Greg Nog said, because that is exactly the kind of thing I'd come up with to avoid the direct approach and because I am not so reasonable.
posted by grapesaresour at 5:16 PM on July 14, 2010

I'd advise against stalking her reading habits as some folks suggested. Unless you're honestly interested in whatever she is reading, don't go out and buy a copy just to score points. It's not a very genuine way to get started, and if she's interested in you, you don't need a silly trick like that.

I'm with the folks who say to push slightly past the "hi" into more cordial chitchat. It might take time, but you'll see over the course of a couple weeks if she's actually interested in conversing with you, rather than being cordial. Seeing as how you frequent this place and she works there, you've got the time. You don't want to be "that guy." If you've had a few conversations beyond "hi, how are you," then go for it, but not before.
posted by SugarAndSass at 6:44 PM on July 14, 2010

try some neutral statements to follow up your greeting, and see if she responds - asking questions sort of forces her to reply or be rude, which she can't be at work, but if you say something that is simply a statment like "it's a nice day" or "one more day to the weekend" she doesn't have to respond -but- if she likes you, and wants to chat further, she can. it's a good way to judge how interested in you she is. If she just says yea, or something like that, she may not be too keen, but if she asks you a question in return, then she's starting a conversation, and you have a chance.
posted by 5_13_23_42_69_666 at 11:42 PM on July 14, 2010

I can tell you that the odds don't favor you if you've been going there for more than a year and all she does is smile and greet you by name when she's on-shift. If she sees you coming in when she's not working, and makes no particular effort to talk to you, then she's either a huge introvert - this is possible! - or more likely, she's not interested.

-Not necessarily, I don't consider myself a huge introvert, and I generally wait for the guy to make the first move (such a bad feminist!).

I agree that, right or not, sometimes I just wait for the guy to make a move. Furthermore, and more importantly, she WORKS there and you don't. It's not worth the risk of awkwardness to her if SHE makes the move and you don't go for it. At least if you make a move and it doesn't go well, you don't have to go there again. But if the situation gets awkward somehow, she still has to come into work every day and wonder whether you're going to show up. that's why if I was her, I would wait for you to make the move.

anyway I agree with the talking-about-what-you're-doing-on-the-weekend approach. it's a good one because it gives the girl an easy out (i am working, going out of town, hanging out with my boyfriend) or an easy in (i don't have any concrete plans, but i was thinking of seeing this movie . . . what are YOU doing?) without it having to be super uncomfortable. for anyone
posted by lblair at 6:34 AM on July 15, 2010