help me flirt in a professional setting
January 20, 2013 9:27 PM   Subscribe

How do I, a barista, flirt with one of my hot regulars?

I'm a part time barista at a cafe, and there's this really intriguing, really handsome young man who comes in every morning and orders a large Americano. I've been there for months and he has been very obviously checking me out for months. When I take his order he usually blushes.

We've never had a conversation but based on looks alone Mr. Americano is exactly my type. I had a hunch that he was smart too (he looked smart and I have good smart-dar for guys), but I wanted to verify before flirting with him because google stalking someone is clearly easier than striking up a conversation with them. We have a customer system where we ask people their names and I took note of his one day and then went home and threw it into google. Turns out he's an astrophysics fellow at a top university. And a hot one. Now I'm even more intrigued. I'm guessing there's a good chance he's taken, but I figure I'd be crazy not to give it a shot.

i have never in my life flirted with a stranger, and it's even scarier since he's a customer. Any suggestions for things I could say, ways I could hint at interest, without appearing creepy or inappropriate? Bear in mind he's a regular so I don't want to make a fool of myself. If I'm making drinks at the bar there's a brief window where we could exchange a few words. The register presents another opportunity but it's more pressured since there's usually a line to the door. Just to give you a picture of my demeanor around him so far, I have yet to smile or make eye contact with him; in fact lately I've been avoiding looking at him at altogether, because cute boys obviously turn me into a fifteen-year-old girl. Also, I'm shy, so I would appreciate suggestions for things I could say that wouldn't require too much sassy delivery.
posted by anonymous to Human Relations (53 answers total) 8 users marked this as a favorite
The problem is that, as a guy, we're told constantly both on MeFi and everywhere else that a barista is NEVER flirting with you. Because too many people think they are when they're just being nice.

So I'd initiate specific conversation. Learn his name (though all my regular baristas do that) and then say something like 'nice shirt' or whatever - something that shows you notice something about him. Ask him about his weekend, whether he's free, etc. Make it clear.
posted by Charlemagne In Sweatpants at 9:31 PM on January 20, 2013 [28 favorites]

Start with eye contact and smiles. As it is, he probably thinks you hate him.
posted by DoubleLune at 9:35 PM on January 20, 2013 [9 favorites]

"I think I remember what you it XXX" (make sure XXX is wrong). "Ohh darn it I was so close. Well next time I'll remember it. And your name, which is? Great. I'm [anonymous]. See, next time I'll remember!"

Then you're all set up to have a cute conversation the next day, and on subsequent days. If he likes you, he'll respond and ask you out after a week of you asking him life questions daily.
posted by Potomac Avenue at 9:37 PM on January 20, 2013 [3 favorites]

Pffft. Be bold. Write YOUR name and phone number on his cup instead of his. When you call his name, hold up the cup at eye level so he sees what you've written and smile. You can't get what you want by doing nothing. Go for it!!
posted by PorcineWithMe at 9:38 PM on January 20, 2013 [107 favorites]

If he hasn't already asked you out, he's probably not going to, even if he'd like to, for the reasons Charlemagne stated. You are probably going to have to be pretty explicit. You need to make some effort to get his contact info so you can call him after work. You don't have to say "I want to go on a date, what's your number?" but you might mention some sort of mutual interest or something in conversation and ask for his number so you could go mountain biking (or whatever), which then becomes a date.

If you spend months on this then you're hours might change (or his will) or something and you won't see him anymore, so I'd try for something that you can do in like 5-10 interactions.
posted by tylerkaraszewski at 9:39 PM on January 20, 2013 [2 favorites]

write your number on his to go Americano? "hey, you're cute" is pretty effective and direct strategy for men.
posted by beepbeepboopboop at 9:40 PM on January 20, 2013 [5 favorites]

Yes, you'll have to be more direct because the entire internet knows by now that it is creepy and wrong to hit on your barista/server.

Maybe you could just jump right in and ask him how come he never buys an extra drink for his gf/bf/spouse. It might at least let you know quickly if he's taken already, and it would give a clear message to him that you've noticed him.

On preview, just go ahead and do what PorcineWithMe suggests. It's full of win.
posted by Brody's chum at 9:41 PM on January 20, 2013

I don't think you should write your name on a cup. This sucks for him if he's attached or not into you. Now he's lost his favourite morning coffee place.

I'd try and "bump" into him outside of your regular environment. Even outside of the cafe is fine, like out front when you're on a break or something. Then you can start a conversation. And suss out the vibe to be sure.

"So you must work around here...?"
posted by miles1972 at 9:48 PM on January 20, 2013 [2 favorites]

When I was 99.9999% sure a worker was flirting with me, it was because she remembered something I'd mentioned in passing 3 months ago. It still took me forever to ask her out because I didn't want to be THAT customer who was weird.

So yeah, I'd just ask him out.
posted by OnTheLastCastle at 9:57 PM on January 20, 2013 [1 favorite]

Calling him Mr. Americano would be cute. Inquiring if he works nearby or even at nearby university X is pretty harmless, and at some point, that gets you to "What do you do there?" such that the information asymmetry is out in the open and he's more aware of your interest.

If this guy is blushing every time he talks to you, it's quite possible that the phone number alone could be pretty intimidating. You might try reading Science Daily or Bad Astronomy so that you can express curiosity about specific things and eventually pull the cup+contact info trick with some obvious cover story that it's to talk about something innocent ("Here's my email--send me your recs for pop science reading!").

He'll probably know what's up, but then he'll also know how to talk to you, and it won't be the kind of thing your management could look at as an issue.
posted by Monsieur Caution at 9:58 PM on January 20, 2013 [1 favorite]

Just smile and act more familiar with him. Slip him your phone no. on the side of the cup or whatever (make sure he's not a serial killer because, you know, Ted Bundy was supposedly goodlooking, well-educated, etc). This guy may have a gf and just like you as eye candy. Be prepared for rejection.

And please make sure that you let male Mefites know that just because one customer is hot enough to catch your attention, it doesn't give most guys the right to hit on baristas.
posted by discopolo at 9:59 PM on January 20, 2013

I've had a lot of wait staff seemingly flirt with me, but I almost always ignore it because:

A) I'm a deeply cynical person and assume that they are just flirting to get a bigger tip,
B) There's a significant power differential since wait staff are supposed to be nice to customers, and it makes me feel uncomfortable to exploit that.

However, my second girlfriend was a bartender (actually, she was my bartender at the place that I was a regular at). We basically started off just having friendly conversations at the bar, then eventually I mentioned some comedy event I was going to and she said "Oh, that sounds like a lot of fun! I've always wanted to do that!" And I, not being born yesterday, took the hint and got her phone number so that we could go there together.

If your astrophysicist is one of the less bright ones (when it comes to social dynamics, not astrophysics) you may need to hint a little more strongly, e.g. "Are you going with a group of people? How much do tickets cost?" Alternately, if he doesn't take the initiative himself, you may drop a few of your own interests instead and see if he goes for the bait.
posted by wolfdreams01 at 9:59 PM on January 20, 2013 [2 favorites]

As you give him his coffee on a Friday: "Hey, have a good weekend! Any fun plans?" (Here you hope he says yes and what they are) "Awesome! I like _____ too. Maybe I'll see you there?" That's if it's something like a flea market or concert or event. Then go and hope you really do see him there. If he says something like, "Yeah, my girlfriend and I are going to spend a day in the country" then that answers the question of whether or not he's available.
posted by Fuego at 10:00 PM on January 20, 2013 [6 favorites]

Yeah, just ask him. A couple years ago I got asked out by an employee at a sandwich place I went to all the time. While I was waiting for my sandwich, he struck up a conversation about a store down the street (I was holding a shopping bag), and we chatted for a few minutes, and then he just said, "Hey, you're really cute, can I call you sometime?" He was really nice and I was very flattered, though I was already in a relationship and told him so. He wasn't weird about it, so it wasn't weird for me to go back there. I think as long as you're not, like, aggressive or entitled or whatever, you're not likely to lose a customer, unless he's a real awkward guy.

On preview, I also like asking about weekend plans, because it gives him a good opportunity to fill in relationship information if applicable.
posted by goodbyewaffles at 10:04 PM on January 20, 2013

In response to the usual greetings, you are always "Better now that you're here."
In response to his usual order, "As you wish."

And Fuego's on the right track. You have to change the context of your meeting before it'll really work to change the context of your relationship.
posted by carsonb at 10:09 PM on January 20, 2013 [1 favorite]

smile, eye contact, compliments. Over and over again.
posted by Ironmouth at 10:15 PM on January 20, 2013 [1 favorite]

Write your name and phone number on a slip of paper, fold it, give it to him. Say something charming like "Hey, here's something extra with your coffee. Maybe you'll like it?" Be sure to blush adorably.
posted by PercussivePaul at 10:21 PM on January 20, 2013 [4 favorites]

"I think I remember what you it XXX" (make sure XXX is wrong).

uh, no. do not play dumb. especially when dealing with an astrophysicist, lol.

just start smiling at him and then when you're comfortable start saying hi. i like the calling him mr. americano. build up to small talk and then see where it goes.
posted by wildflower at 10:30 PM on January 20, 2013 [13 favorites]

If a barista, bartender, or any other service industry person wanted to let me know they were into me, they would have to be pretty bold. As in, "hey, here's my number, call me sometime" or "hey, I get off in an hour, do you want to go get a beer?" bold. Anything less and I would assume they were just being nice and/or trying for a good tip. I have worked extensively in the service industry and have known many women who have done so as well, and the rule is that unless they basically hit you over the head and drag you away, they are just being nice and/or trying to get a good tip out of you.
posted by Scientist at 10:47 PM on January 20, 2013 [23 favorites]

I love the name and number on the cup idea. If you want, chat him up first so he knows it's your name and number. And you are allowed to flirt! Do it!
posted by two lights above the sea at 10:54 PM on January 20, 2013 [1 favorite]

You could also write messages to him on the cups if you really think he's shy? But I say go bold.
posted by two lights above the sea at 10:55 PM on January 20, 2013

OK, combining several suggestions got me this: write him messages on the cups, progressively flirty ones- see how he responds. Warm him up a bit, and then after 3 cup messages the next one is your number and something specific you would like to do with him, and that coffee is on the house.
posted by saraindc at 11:27 PM on January 20, 2013 [10 favorites]

I fully endorse saraindc's plan.
posted by PercussivePaul at 11:31 PM on January 20, 2013 [2 favorites]

The overwhelming advice to patrons in your guy's position is "Do NOT hit on the barista; s/he is being nice to you because it's their job." So honestly, I'd just give him his Americano with your number and a post-it that says "Mine's a latte. Call me if you want to get coffee! -- Jane." stuck to the cup.
posted by DarlingBri at 12:05 AM on January 21, 2013 [12 favorites]

In response to the usual greetings, you are always "Better now that you're here."
In response to his usual order, "As you wish."

I would find this weird. Be direct; you will have to be direct. Something like: "Hey coffee's great, but would you like to get a drink with me some time?"

Keep it casual and relaxed. Easy peasy. Don't worry about him freaking out; 99% of the time it's very flattering (as a guy) to be asked out. It doesn't happen (at least to me! ;) very often, so it's a nice compliment and it never fazes me.
posted by smoke at 1:44 AM on January 21, 2013 [3 favorites]

Hey, look, I know you're shy. He's shy too or he wouldn't be blushing, he'd be just asking you out. But you're the employee, he's the customer, and the onus is on you to break the wall if he's going to play his role like a proper customer.

Does he come at a certain time of day? Regularly? If you can predict or plan when he'll come, I suggest taking a break then -- or coming in on your day off, if possible -- and approaching him on his way in, or out, of the shop. Even if possible just warn your co-workers that you might take a sudden five minute break to run out after him. Anyone who is cool will be down with that, it's just like a million rom-com set pieces.

This removes the context of employment and means you are both peers.

And also, if he has even a tiny bit of sense about him, he'll recognize you outside the shop, as you come up to him. And then he'll simply have to acknowledge, internally, that you have a non-professional interest in him. After all, why else would you approach him?

As for what to say, I suggest with the perfect icebreaker for shy people: "Hey, I'm really shy, and this is hard for me, but I'd like to get to know you better. Would you like to sit down for a coffee now or some other time?"
posted by seanmpuckett at 4:32 AM on January 21, 2013

Pffft. Be bold. Write YOUR name and phone number on his cup instead of his. When you call his name, hold up the cup at eye level so he sees what you've written and smile. You can't get what you want by doing nothing. Go for it!!

A friend of mine did this while working as a barista. Her story was nearly identical to yours - obvious chemistry, guy was a regular, etc. They've now been married 5 years and have two gorgeous children. YMMV, but what's to lose?
posted by pecanpies at 5:41 AM on January 21, 2013 [9 favorites]

"Siiigh. I suppose you're another cutie who is already in a relationship".
posted by notreally at 6:03 AM on January 21, 2013

Okay, I'm going to go against the grain here and say that you should talk to him first and build up rapport before handing him your number. I think I would be totally weirded out if the barista at my regular coffee spot just handed me their number without ever talking to me the dozens of times I had already been there.

At least if you engage in some small talk you can feel him out and gauge his interest. Start off with old reliable, "How are you?" or "How was your weekend? Do anything interesting?" etc...
posted by joeyjoejoejr at 6:28 AM on January 21, 2013 [10 favorites]

Here is your script.

"It is so nice to see you! Americano today?"

"So what do you do around here when you're not drinking coffee?"

"Really? That is fascinating! I wish I knew more about astrophysics. Do you like it?"

"Here's my number -- maybe you'll call me and teach me a little bit about astrophysics sometime."
posted by Mr. Justice at 7:18 AM on January 21, 2013 [4 favorites]

I'd have to agree with miles1972--please don't flirt with him at work. I'm so surprised that so many people are all on board with this "customer-serviceperson pick up scenario". It's not okay, regardless of the initiating gender and regardless of which gender and/or initiator is behind the counter.

If you're interested in him, please try to figure out how to run into him outside of work. Right now the only thing you actually know you have in common is that the coffee shop he stops at each morning is convenient for him. Rather than internet stalking him, you can start up light conversation and discover whether you actually might share a common interest, and thus figure out how to run into each other, or it might even just end up happening spontaneously: You: "Oh, you always order my favorite drink! This morning I went with the double triple large because I was up late watching the meteor shower last night." Him: "Oh, seriously? I'm going to be watching it again tonight through my super special telescope tonight at the science museum, maybe I'll see you there."
posted by gubenuj at 7:39 AM on January 21, 2013 [4 favorites]

I don't think you should write your name on a cup. This sucks for him if he's attached or not into you. Now he's lost his favourite morning coffee place.

Oh pshaw. I go back to my usual place every couple of days, even though I know the barista is going to flirt, even though there's no circumstance on this earth under which I'd date him. He hasn't written his name on a cup, but always says, "let me know if you ever want to hang out." To which I always just laugh and wave goodbye.

It barely clears the "moderate" bar of awkward. I'm amused/mildly flattered, he seems to enjoy the flirting regardless, everyone goes about their days.
posted by like_a_friend at 7:57 AM on January 21, 2013 [2 favorites]

Oh yeah...also, I met the last person I dated while he was working as a barista. We bonded over the Kinks (often played in the coffee shop, a favorite for both of us.) He memorized my name and drink order, made a point to chat me up a bit, just "how was your weekend" etc. And then at one point I finally said, look, you clearly know my name, what's yours?

He blushed five thousand shades of purple-red, and stammered his name out like 3 different ways, and it was off to the races :)
posted by like_a_friend at 8:01 AM on January 21, 2013 [2 favorites]

I met my husband while I was working as a barrista. Mine was a Mr. Latte instead of Mr. Americano -- everyone I worked with had noticed my crush. I started making his drink before he got to the register, and I handed it to him, here you go Mr. Latte. We started chatting mroe when he came in, and I tried to schedule my breaks for when he usually came in. I asked if he worked near by, and he started coming in more than once during my shift. I got a lucky break, and a coworker basically forced me on him. I don't think he would have ever asked me out, because of all of the stigma mentioned above, so I would just be friendly, and if it gets chatty, just ask him out.

Good luck!
posted by hrj at 8:06 AM on January 21, 2013 [1 favorite]

Doing this sort of thing at work, in public, is distasteful in my opinion. If you're gonna do it, do it on the sly - slip him a note with his coffee (as stated above, don't write it on the cup). "Hi - I see you every morning and would like to get to know you better. Here's my number - call me."
posted by brownrd at 9:27 AM on January 21, 2013

Yeah, I disagree with most people here. Flirting at work with anyone, especially a customer, is kinda icky and probably a fireable offense.
posted by roomthreeseventeen at 10:19 AM on January 21, 2013

Can you have a co-worker cover for you for five minutes while he's there? Then make a cup for yourself, stroll over to his table and say "Oooh, what a morning it's been! Do you mind if I sit down here for a minute?". As others have said, it's good if you single him out among the other guests so he doesn't think you're just nice for the tips.
posted by springload at 11:02 AM on January 21, 2013

Why not start talking with him about astrophysics? Read something interesting, and ask him a question.
posted by 3491again at 11:06 AM on January 21, 2013

Talking to him about astrophysics might clue him into the fact that you've internet-stalked him. I'm thinking it would be a better idea to talk about astrophysics only after he himself tells you his field.
posted by rozaine at 11:47 AM on January 21, 2013 [2 favorites]

Since he's in there regularly, I'd say your goal should be to create frequent light interactions that have the potential to evolve over time, rather than jumping in with both feet before you've even tested the water. I find that asking "Having a good day?" (or "Rough day?" if they look unhappy) is a good way to open the door to a quick conversation without much pressure. Also, comments on the weather or local sports teams (if you're a fan) are always reliable conversation starters. (I agree with rozaine on not going straight for the astrophysics questions until he tells you that's what he does - otherwise it seems a bit stalker-y to me.)
posted by platinum at 11:50 AM on January 21, 2013

I was coming here to write the same thing as PorcineWithMe.

On his cup, write:
"You're handsome. I'm Laura."
posted by 2oh1 at 2:28 PM on January 21, 2013 [1 favorite]

Start smiling at him!

Say something like "It's always nice to see you! How's your morning going?"

If he mentions something, comment on it next time. Ask how it went or whatever.

Baristas don't get fired for making light flirty conversation with customers, people worrying about that are thinking of other types of jobs.
posted by yohko at 3:09 PM on January 21, 2013 [2 favorites]

Do what my friend did when she was interested in the dude who was coming into the bar a lot and asking for her. "Hey here's my number, call me some time." and she put a slip of paper into his palm and then went on with her waitressing duties.

They've been married for 12 years now?
posted by 922257033c4a0f3cecdbd819a46d626999d1af4a at 4:05 PM on January 21, 2013 [2 favorites]

if you slip him a note, it would be nice to give him an easy out if he's not interested, just to avoid awkwardness - like:

"call me if you'd like to hang out - #### - but for all I know you have a girlfriend, so if I don't hear from you, no worries, I won't be offended"

then make sure you're still friendly to him the next time he comes in
posted by 5_13_23_42_69_666 at 7:18 PM on January 21, 2013

call me if you'd like to hang out - #### - but for all I know you have a girlfriend

I would change this to "but for all I know you're in a relationship" because he might be dating someone who isn't a woman. There just isn't any way to know so I think it's best to be non-specific!
posted by DarlingBri at 4:21 AM on January 22, 2013 [2 favorites]

I love the name on the cup idea, it's very cinematic, but don't do it. I think Potomac Avenue's "oh I remember you, you like XX" but getting XX wrong is deviously clever, as it opens the window you are looking for without backfiring in any kind of way. After you chat, he will know for sure when he comes back (which he will), that you remember him and that he can greet you like he knows you, and that chatting is cool and ok.
posted by molecicco at 6:13 AM on January 22, 2013 [1 favorite]

And it worked for like_a_friend's barista admirer!
posted by molecicco at 6:14 AM on January 22, 2013

I've been on the other end of this (and wished I'd been on the other end of this at some points) and all I can say is, jeez, just smile at the guy and say hello, how's it going? Need the shot of caffeine to start the brain? Why, what do you do? Oh, I'd love to hear more some time. I go on break at ...
posted by RedOrGreen at 8:19 AM on January 22, 2013 [1 favorite]

So... I'm kinda curious as to what happened. Any updates?
posted by rozaine at 3:04 AM on January 23, 2013 [10 favorites]

Mod note: From the OP:
Put my number on his cup. He never called. Girlfriend or not interested? Guess I'll never know. :/ Fortunately my shift has changed to the afternoon/evening so we are unlikely to cross paths again.
posted by restless_nomad (staff) at 3:12 PM on February 1, 2013

Shame it didn't work out, but I am proud of you! It is courageous to put yourself out there.
posted by PercussivePaul at 5:22 PM on February 1, 2013 [2 favorites]

Mod note: From the OP:
Great news! Turns out he never got my number before (long story). It's too lengthy to explain how but I found out he never saw the note I had tucked into the sleeve of his coffee. So I put another, more conspicuous note on his Americano cup this morning. And ten minutes later he texted me and asked me out. We have a date in two days!! :P
posted by mathowie (staff) at 4:53 PM on February 21, 2013 [21 favorites]

Yay!!! And hey, seriously awesome to slip your number to him a second time. I hope you have a wonderful time on your date!
posted by PorcineWithMe at 3:20 PM on February 22, 2013

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