Tables for Two: Picking Up the Waiter

What time do you get off?


You're sitting at a bar, enjoying the pleasant warmth of three glasses of wine and fifty flickering votives. A friendly stranger comes over to talk and brings you a drink. She makes eye contact, smiles big, and laughs easily. She is, in other words, obviously flirting with you. Unless, of course, she's your server. In a job where your wages are determined not by hours worked but by your rapport with a series of strangers, a smile that feels like a come-on is sometimes about paying the rent.

Now, most servers I know are pretty sincere people whose smiles aren't faked — real enthusiasm is part of helping everyone have a good time. But that doesn't mean that the happily married bartender doesn't sometimes wink back at a woman he'd ignore after work. It's not deceitful; it's part of the job.

Except, of course, when it stops being part of the job — lots of us have infatuations, flings, and sometimes long relationships with people we met at work. As a waiter, I've seen the scenario play out every possible way. Here are five guidelines for success:

1) Don't let your friends get in the way

Lots of us have infatuations, flings, and sometimes long relationships with people we met at work.

Tiffany is visiting from Los Angeles. Joanna just locked in a location for her wedding, which calls for a night on the town with six or seven friends. Before they've even ordered their prosecco, I know their names, who is and isn't from New York, and their reasons for celebrating. How? Because they tell me, in that wonderfully over-communicative way of women getting drunk in groups. The woman on the corner, maybe a Rachel, lets me know about Joanna's engagement and vows that they're "gonna get hammered" — a proclamation that's met with cheers and mimed clinking of their not-yet-delivered glasses. 

The move: As per the bylaws of "girls' night out," they will get louder after dinner, goad one another into ordering dessert, and hit on their male waiter. Despite the fact that I'm ten years their junior (and would prefer a date with a younger brother), it's as inevitable as group trips to the bathroom. Sassy Rachel on the corner makes the comment — something about my "hot body" (I should note that the restaurant is forgivingly dark) — but says it loudly, with a grin. It's well-intentioned, and if I feel uncomfortable, it's fleeting — certainly less painful than Lindsay the bartender's concurrent experience with a group of guys'-night-out bankers. The ladies leave a generous tip, and a business card. Her name is Rachel and she's an architect.

The result: I kind of doubt she's serious; the card seemed mostly to be for the amusement of the group. All the obvious factors notwithstanding, I pin her card up on the bulletin board in the back, tell the story as a joke to my friends, and don't even consider calling. She wins points for being direct, but if you want to hit on your server, don't do it in front of your giggling friends. 

2) Man up

It's date o'clock — 9:15 on a Friday — and a young pair, a man and a woman around my age, sit in my section. While I recite the specials, she nods attentively and he studies the menu. They're dressed up but seem comfortable. I'm thinking it's probably around their fifth date, until he looks up and smiles at me. Nope, just dinner between two best friends after a night of opera.

The move: For most of the meal, I chat with his talkative companion, and try, in vain, to engage him. He smiles, but says nothing, until they're on their way out. As I'm saying my "thanks-have-good-nights," he turns and awkwardly proffers his hand, "I'm Tim." He stutters something about seeing one another again, and then disappears, without giving either of us the faintest means by which to follow-up.

The result: Frustration. Telling me your name, Tim, just let me know that you're not as smart as you are cute. I know sometimes it's hard to make the first move, but if your target is currently pouring you a drink, filing your taxes, or pushing the gurney, you have to. If you'd hung around to leave a number, you'd risk fifteen seconds of discomfort. If I'd chased after you, I'd risk losing my job. So, man up. 

3) Watch your drinking

They're both blonde, in-shape, and strikingly similar-looking. It's not until they start holding hands that I answer my mental question: "Brothers or boyfriends?" They seem happy, polite to me and physically affectionate with one another, in a cute-not-nauseating sort of way (a distinction that falls sharply between sharing a piece of cake and feeding it to one another, between hand-holding and same-side-of-the-table sitting). They order the third bottle of wine; I assume they must be celebrating.

The number-one rule of hitting on a server is to know how drunk you are, followed closely by remembering that I'm not.

The move: After dinner, the one stands, lurches, and asks me where the bathroom is. He follows me down the corridor, and then, out-of-the-blue, puts a drunk hand on my shoulder. I'm hardly trapped, yet I'd have to push by him pretty brusquely to walk away. Close enough for me to smell the wine I'd sold him, he suggests we "get a drink sometime," and ducks into the bathroom. 

The result: I ask a buddy to drop their check, then go smoke a cigarette to avoid seeing them on the way out. The number-one rule of hitting on a server is to know how drunk you are, followed closely by remembering that I'm not. Rule number three is don't be aggressive. Especially when I'm at work, and am therefore professionally obligated to be much more polite to you than you deserve.

4) You win some, you lose some

Two young women sit at table seven, looking like the pretty nerds of '90s high-school rom-coms, pre-prom-transformation. (In other words, they're still wearing their glasses.) They ask good questions about the specials, and then take about one-third of my recommendations, which makes them seem restaurant-savvy but not pandering. One compliments the music (Bowie, from my iPod) and the other sings along for one pitch-perfect British line. Charmed, I send them something small from the kitchen and think that we could probably all be good friends. 

The move: While one's in the bathroom, I stop by to clear the remaining plates. The other starts chatting to me about drinking, bars, bars in the neighborhood, bars I might accompany them to, perhaps a sensible exchange of phone numbers to facilitate such drinking, and like an idiot I'm bumbling along, smiling, and thinking, "Oh, what fun!" until I notice friend B, not in the bathroom but politely lingering out of ear-shot, a sexiled freshman watching cartoons in the lounge, letting her friend take care of business. 

The result: I take her phone number, like a jellyfish. But what else can I do? Say no and I feel mean. Say, "I'm in a relationship?" Then I sound stupidly presumptuous. Stutter something stupid about preferring the original cast of Rent and hope that she gets it? By the time I finish up, I feel less nervous — maybe they do just want to be buddies — and so I text and say hi. She writes back and says her friend headed home, but she's still at the bar around the corner. I panic, text an excuse, and turn off my phone. She did everything right, so I guess the only lesson is — you win some, you lose some. Or that I'm an asshole.

5) Be charming

The lesson is — you win some, you lose some. Or that I'm an asshole.

He looks kind of like Dev Patel, cute as a button with a mischievous smile. I notice him before he notices me, while he's still waiting at the bar. His dining companion arrives, a guy he greets with a hug that clarifies nothing about their relationship. It so happens that I'm happily dating someone myself, but it hardly matters. If my life were an Archie comic, I'd trip over myself to carry his books and spend my last five-spot to buy him a malted. 

The move: Since I'm assuming he's on a date, I keep my lecherous thoughts confined to an overly enthusiastic description of the specials, a big smile, and — okay, okay — a gay-waiter clap (a move I hate but sometimes can't help; if you've seen it, you'll know what I mean). And then, smiling fiendishly, he asks for an order of Kettle Chips — not on the menu, but which I have been eating (I thought surreptitiously) in the wait station all night. The ice is broken, I laugh, and we chat amicably — to the detriment of my other tables — each time I pass by. He's a student, in town from London, and very forthright about being 'just friends' with his dining companion. When they get up to leave, I find a cute drawing, indicating which of the two diners left the note (as if I wouldn't have known), an invitation to "eat Kettle Chips" and a phone number. 

The result: First off, a grin. Boyfriend or not, there's nothing offensive about a charming pass from a handsome stranger. We text one another wittily for two weeks before he flies back to London. When you have ninety-minutes, and your conversation is mostly burdened by logistics, it never hurts to be direct. Being absurdly adorable is also a plus.

Commentarium (11 Comments)

Jul 12 10 - 6:02am

This is kinda awesome

Jul 12 10 - 10:37am

Good, straight forward, and funny advice

Jul 12 10 - 12:03pm

This is brilliant!
More please?

Jul 12 10 - 5:25pm

These are great! I wish he would've txted the girl in #4 that he was gay; she probably would've been relieved to know she wasn't being ignored because she looked like a pre-prom nerd.

Jul 12 10 - 6:39pm

fabulous! scenario 4 could have taken some advice from scenario 2 and yet still a great article

Jul 12 10 - 6:42pm

I love that it finishes on both a solid tip and a positive note :)

Jul 13 10 - 6:23am

Seems the biggest rule is 'be attractive'. Great read, nonetheless.

Jul 13 10 - 6:28am

I bet this waiter is tall with good bone structure

Jul 13 10 - 7:19am

I married my waiter.

Jul 15 10 - 10:17am
harry krishna

whew. this is not good.

Jul 15 10 - 8:34pm

I love this segment. excellently written.