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02 March 2009

DRAMA! AskMeCha: need some dating help... [More:]Anyone ever successfully asked out someone that provides them a paid service (not that kind of service lulz)?

Here's the situation: I have a bit of a crush on the woman who cuts my hair.

I've been going to her for a little over a year (essentially the whole time I've lived in this city). We've always had pretty easy conversation. She's read at least one book I've recommended (a finance/econ book, no less, which is my profession). She has a sardonic sense of humor very much like my own.

Through our conversation, I know that she's single and recently bought a condo in my neighborhood. She has mildly complained about bad luck on first dates and being alone of Valentine's Day.

I haven't notice any clear-cut signs that she's interested in me romantically. But my track record tends toward obliviousness and I don't know how demonstrative she is anyway.

Normally the awkwardness of the situation would scare me off entirely. But, to be honest, I've not made much of a social or romantic life for myself since I've moved here and I'm starting to get restless. Not that I'm only interested in this woman because I'm lonely; rather, I'm considering what is for me an "advance maneuver" in dating because I got to start somewhere and she's the most person I'm most interested in.

But how do I do this? I can't imagine sitting in her chair with a cape draped over me and asking her out while she cuts my hair. Not to mention all the other employees and customers within earshot.

Is this just a hopeless awkward scenario? Am I kidding myself about what she may or may not think about me?
"alone on Valentine's Day"?!

I read no further. Dude, that was no subtle hint, that was a 10-pound sledgehammer.

posted by Ardiril 02 March | 11:50
Hah to the sledgehammer comment! Yep.

Yeah, but why not simply mention some event of common interest and see if she'd like to meet there?

Or, start getting your hair cut every week. That should be pretty obvious- maybe she'd make it easy for you and just give up and ask YOU out?
posted by mightshould 02 March | 11:54
Is there any way you can "accidentally" bump into her (without stalking her)? Or, alternatively, next time you get your hair cut can you forget something in the chair so that you have to go back to the salon, whereby you can have a conversation with her that doesn't involve sitting in the chair?
posted by mudpuppie 02 March | 11:55
I don't think it's hopelessly awkward. I think you should ask her to dinner or some event after your next haircut, right on the way out the door ("Oh, I was meaning to ask you- I have tickets to see the WSO next weekend, would you like to come with me?") If she says no, you have until the next haircut to get over the shame of it, at which point you have to get over it, go back to her for your haircuts, and laugh at her on the inside when she bitches about being single, because, hello!
posted by ThePinkSuperhero 02 March | 11:58
OK, I see your other issue. Try this. While in the chair, find out her work schedule. Then, these places all have products to sell. Steer her into an area away from others as though you were shopping. Then say, Look. To be honest, I would like to see you some time. How about coffe on Saturday?

... or whenever her free day is, which you now know.

Failing that. Talk to her at the cash register. If that opportunity does not exist, only go in with 20s in your pocket so you need to get change to tip her. Then talk to her.

Think on your feet and adapt to the situation.
posted by Ardiril 02 March | 12:00
Do what TPS says. You'll be a nervous wreck the entire haircut, she'll probably be able to tell, but keep it cool and wait until right before you leave to ask her out. The worse she can do is say no.
posted by stynxno 02 March | 12:06
Well, to be fair, in general the worse she can do is say no. But in this case, the worse she can do is say no while holding a pair of scissors to mullacc's head. Think about THAT for a minute.
posted by mudpuppie 02 March | 12:08
Unfortunately there's a bit of a weird hand-off between her and the cashier. I think I can figure out something to do during that time.

The other advice I got was this: on my way out, give her my card and say, "I'd love to grab a beer with you sometime." Putting it her court kinda removes the customer/service provider issue, but it's also kinda passive.

Is there any way you can "accidentally" bump into her (without stalking her)?

Honestly, we live so close that I'm surprised we haven't already. If I could engineer this without getting stalky, that would be great.
posted by mullacc 02 March | 12:11
You HAVE to do this now, 'heen! I want follow-up details. Best of luck, man! N-thing everything said upthread. If she's as cool as you think, even asking her out and getting a "no" back will be done with class and not affect any future hair-cutting appointments.
posted by Lipstick Thespian 02 March | 12:12
Putting it her court kinda removes the customer/service provider issue, but it's also kinda passive.

The problem with putting it in her court is that she may be as nervous about it as you are, and may talk herself out of making that call, and then if you follow up, you look pushy.

Here's another thought. If you know you have some common interest (or if you know one of her interests and can pretend to be into it), bring it up during the haircut. Have an enthusiastic conversation about it and steer the chat towards "Oh, yeah, I really love elephant art too! I hear that the show down at that new Modern Elephant Art Gallery is really great. We should go check it out!" You just have to have an end goal in mind ahead of time.
posted by mudpuppie 02 March | 12:18
The other advice I got was this: on my way out, give her my card and say, "I'd love to grab a beer with you sometime." Putting it her court kinda removes the customer/service provider issue, but it's also kinda passive.

Totally. You don't want to go out for a beer "sometime" - going out "sometime" is for those things you never actually end up doing. When someone says, oh, let's go out sometime, I say, yes, let's go out sometime- and then it rarely ever happens. You gotta take it to the next level- let's go out Friday, next week, whenever.
posted by ThePinkSuperhero 02 March | 12:20
Yeah, I tend to agree with setting up a concrete event/time.

You HAVE to do this now, 'heen! I want follow-up details.

Thanks for the encouragement--but, you'll have to wait a few weeks since my next appointment isn't until March 22nd.
posted by mullacc 02 March | 12:26
I wouldn't make her call you -- there might be ethical weirdness (justified or not) about asking out a client, even if there's not any weirdness about accepting a date from a client.

I would follow TPS's advice; it seems the most straightforward, non-manipulative, and non-scissory. :-)

And good luck!!!
posted by occhiblu 02 March | 12:46
Maybe send her flowers, with a note and your phone number? True, the ball's in her court then, but it gives her an excuse to call you, thank you for the flowers (given she knows you well enough to recognize your name, of course). Or just stop in and ask her, be direct. Like folks say, worst she can say is no. If you wait until the next hair cut, she may meet someone in the meantime. If she's telling you where she lives and she's "alone on Valentine's Day" it definitely sounds like she's hinting. Of course, if it turns out to be just hair stylist chit-chat, you may have to find another stylist. But hey, if it works out, free haircuts. :)

on preview: I guess March 22nd's not that long... maybe send the flowers a day or two before your next appointment?
posted by Pips 02 March | 12:46
Though I want you to ask her out somehow or other, and it sounds like she might accept, I'm going to be the lone contrarian here.

Hairdressing is one of those professions - like bartending or waitressing - where you're captive to your customers, in a situation that has an illusion of intimacy, and unable to not be nice. If you choose to ask her out while she's at work, please be sensitive to this. It sounds like she could be open to being asked out, but I'm trying to think of a way you can make it clear that you want to connect without putting her in that really awkward situation of 'oh, my clients are hitting on me. Again.'

On the other hand, she probably has methods of dismissing that, so maybe I'm overly concerned. The fact that she talks about being single means that, at least, she's not averse to you. If she didn't want you hitting on her, she'd make up some kind of pretend boyfriend to talk about.

I just wish I could think of a classy way for you to do this so that it's not intrusive that you're asking her out while she is basically hemmed in at her work environment. That's why I like the flowers, or leaving a card - it lets her take control at a time when you're not right in her face. Yes, I agree that "sometime" is too vague and makes her do too much guessing - so why not leave a card saying "I'd like to go see [exhibit] on Sunday the 16th - if you're available and would like to go, please call me at [number]."
posted by Miko 02 March | 12:59
If she's in your neighborhood & I'm assuming new to it, can you just mention such & such bar or restaurant - ask her if she's tried it yet, and if not, invite her to join you? You could also invite her to join you with some other friends to be less threatening and decided whether you really do want to date her. Could you call her at work instead of waiting for the next haircut? Or drop a note by?

I sucked at dating, and I still suck with people so take with grain of salt.
posted by chewatadistance 02 March | 13:19
Just call and ask her out for a drink. Done and done. Be prepared to get your hair cut somewhere else, though.
posted by eamondaly 02 March | 13:54
I agree with Chewie and eamon. A bar or art gallery in your neighborhood is good:

If it turns out she isn't interested, you were just being friendly.
If it turns out she is interested, well hey you were interested too!

Re. what Miko said, it can definitely go either way. When I worked retail, some people would chat up customers, read their books, tell them about their private lives, go to an art opening, and then be shocked... SHOCKED that they were evidently on a date. I was all business unless someone was really interesting. I never ended up in a ZOMGISTHISADATE?! situation. You don't know which way your hairdresser falls. Keep it in mind when you put the invitation out there.

Look at it as an experiment or imagine it's a Request for Proposal of sorts. Good luck!
posted by halonine 02 March | 13:59
"sometime"

Never ask sometime, make it a specific day, say Friday. If she says, no. Ask for Saturday. If she says no again without suggesting an alternative, you are just wasting your time.
posted by Ardiril 02 March | 13:59
Flowers and/or a note are just really not my style. I appreciate the ideas, but I can't pull those off. Now, if she were on Facebook, I'd totally use that. But, alas, no.

But I am absolutely trying to consider Miko's warning about putting her in a weird spot. Hopefully I'll come up with a seemingly-natural date/meeting suggestion and use that as I make my exit to the cashier. If I get a weird reaction, I can play it down.
posted by mullacc 02 March | 14:04
How about suggesting that, as she was alone on Feb 14, she might instead like to share March 14 with you ...

I keed, I keed ... ask her out for coffee.
posted by essexjan 02 March | 14:36
OMG essexjan that site is HILARIOUS.
posted by Melismata 02 March | 15:03
I'm not crazy about the flowers... it makes it too heavy, I think. I'd go the TPS way; or call her, if you don't want to ask in the chair. Also, it seems like she's tried to open up the door to that by mentioning being alone on Valentine's day, so I'd be surprised if she wasn't thinking along the same lines.
posted by taz 02 March | 17:18
Try this:
≡ Click to see image ≡
posted by jonmc 02 March | 18:19
"This may seem awkward to you, but think of how brave it is of me -- considering you have scissors near my ear lobes. But I've enjoyed our chats while in the chair, and I was wondering if we could spend more than 20 minutes talking somewhere else sometime? Maybe dinner at ________."
posted by terrapin 02 March | 18:23
jonmc: I think I'd have to write it out backwards so that she can see it in the mirror.
posted by mullacc 02 March | 18:25
Palindrome.
posted by box 02 March | 18:27
mullacc: that message is on a pack of these candies. (they mix it up)buy a pack and give her one while looking up winsomely.
posted by jonmc 02 March | 18:33
Palindrome

Her name wouldn't happen to be "Elba" would it?
posted by taz 02 March | 18:34
Eve?
posted by Hugh Janus 02 March | 18:37
what

Now I'm just confused and hungry.
posted by mullacc 02 March | 18:40
"Able was I, ere I saw Elba"

Smoove? Always good when a potential date knows you are "able". Nudge, nudge, wink, wink.

We're just playing now. After TPS and terrapin, we have nothing left to advise because they hogged all the good advisin'.
posted by taz 02 March | 19:01
he goddam mad dog, eh?
posted by jonmc 02 March | 19:07
We're just playing now.

Oh ok. Also feel free to use this thread to tell me how charming and attractive I am. Tks.
posted by mullacc 02 March | 20:07
i'd hit it, mullacc
posted by terrapin 02 March | 20:21
Try complimenting her on the haircut, that whenever you go to her, and get one done, you feel like a new man, and that this might be a little forward of him--but would she like to go out with you sometime--and that it's okay if she doesn't want to: she already has a customer for life, or as long as she stays/lives close by.
posted by hadjiboy 02 March | 20:27
feel free to use this thread to tell me how charming and attractive I am.
≡ Click to see image ≡
posted by jonmc 02 March | 20:28
lulz.
posted by ThePinkSuperhero 02 March | 20:40
Don't do the advance flowers! It will make a potential "no" much more uncomfortable. Ask after the haircut.
posted by Meatbomb 02 March | 22:18
I'm in the giving her your card and asking her out for coffee camp.
posted by brujita 03 March | 00:14
I misread that and constructed "coffee camp" as a place. It sounds like a great idea, Coffee Camp. I would go to that if someone asked me!
posted by Miko 03 March | 00:28
Oh, well. Guess some folks aren't into the flowers. Guess I was assuming she's into ya. If she is, I'm sure she'd love it, but if not, I could see how that could be awkward. Good luck anyways!
posted by Pips 03 March | 12:26
I would ask by telephone. Asking as you exit is potentially cringe-y, as all ears in the vicinity would perk up. Plus, her saying "yes" or "no" will be easier by telephone. Also, no flowers.
posted by Claudia_SF 03 March | 13:57
Heee, Miko!

Mullacc, has she been giving you little touches other than your head while she gives you the haircut? If yes, all systems go.
posted by brujita 04 March | 01:00
Really Really Really Really Real || Peeps, when you go to the doctor, you might wanna .....

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