Big Questions

Should You Flirt With the Wait Staff?

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young people having fun in a cafe

When it comes to hitting on bar staff, they’re sitting ducks. Trapped at work, obliged to be as nice as possible, and working for the tips, flirtation is an almost necessary part of their jobs. At least, that’s what we tell ourselves after our third cocktail, swaying on the barstool, finding other patrons ambivalent to our existence, with only the bartender paying us any real attention (even if that is just to ask “Another Negroni?” when you’ve sipped your glass dry). It’s a muddling of the professional and the social; especially because general perception often generates the assumption that bartending isn’t a real job anyway. As a result, we engage in behavior that we wouldn’t with say, a cute dental hygienist when getting our teeth cleaned, or with a police officer on the beat.

The first time I took it upon myself to objectify a bartender, I wrote my name on a one dollar tip and slid it across the bar. My friend Alice and I were drunk and trying to figure out how to make it obvious there was a phone number on the note, lest the bartender I’d been flirting with just bundle it up with all his other tips and shove it into his pocket. She snatched the note from me and tried to put it in the leaves of the festive poinsettia on the bar.

“No!” I shrieked, snatching it back, “That just looks crazy.”

“You just wrote your number on a one dollar bill,” Alice said laughing, “You’re basically paying this guy to call you.”

From all the commotion, the bartender came back over to where we were sitting. “Can I help you ladies?” he asked.

I hyperextended my elbow to thrust the note into his face, bleating awkwardly, “Here’s your tip. It has my phone number on it.”

As I expected, the note with my number on it got lost with all his other tips. But the sentiment had its intended impact; a few days later the bartender Alice had been hooking up with (a coworker of my mark) messaged me on Facebook to ask for my number on behalf of my crush. What followed was a fruitful two-odd years of us occasionally sleeping together, most of our efforts hampered by his working nights, and my working days.

Excitement vs. annoyance seems to come on a sliding scale of the comparative creepiness of the situation.

I’ve noticed that, generally speaking, picking up bartenders is something of a dating trend amongst young women. My friend Jennifer, who works 9 to 5 as a creative in Manhattan, has been flirting with the bartender at our local ever since she forgot her gym bag at the bar one time and had to go back to fetch it. Of the beginnings of the flirtation, she tells me, “This cute bartender gave me my lost gym bag and I decided I might as well stay for a drink. I ordered a hot toddy, and the water was taking forever to boil. He was apologetic and we were laughing about it and flirting a little. That’s the nice thing about going to a bar alone in the early evening on a Tuesday night, there’s basically no one there and you can just sit and chat with the bartender while he makes your drink.”

In New York, a city whose heart beats with the very essence of sex, there seems to be but one constant: the bartender. He’s about as reliable as it gets. His references check out, you know where to find him every week, and chances are he’s not a total axe murderer (and even if he did turn out to be one, at least the police would know where to find him when your chopped up body turned up in the Hudson).

But I’ve been on the other side of the equation too, having worked as a hostess in an East Village restaurant. The whole work/flirtation thing was certainly not as cute when sleazy guys were clicking their fingers at me and tapping my ass on the brunch shift. Although for me it was always a matter of who was hitting on me. One afternoon some good looking young guys came in, and invited me and one of the waitresses to a party they were having. Because they were cute, polite, and my age, their attention became an exciting addendum to a double shift. Excitement vs. annoyance seems to come on a sliding scale of the comparative creepiness of the situation.

My friend Jamie, a bartender in Williamsburg, feels much the same way about being hit on while she’s working. “If the bar is insanely busy and someone is trying to flirt without being sensitive to the fact that 20 other people are standing behind them frothing at the mouth for a whiskey shot and beer combo, getting hit on is just stressful,” she says. “At the other end of the spectrum, it sucks when the bar is incredibly dead and the person hitting on you has the smug look of someone who knows they have you trapped because there are literally no other customers to act as a buffer between you and their asinine questions and clumsy attempts at double entendres.”

Even though being hot on at work can be awful, there are some times it’s worth it. “But resting in between those is a lovely middle ground where at worst, you get to engage in some witty banter that makes the hours go by faster, and at best you get the quite lovely experience of being hit on by someone you find attractive and interesting,” Jamie says. “I think it all boils down to the power dynamic. As a bartender, you’re in something of a position of power, which is why being hit on can often be less uncomfortable or threatening than it is in regular life.”

It all boils down to the power dynamic. As a bartender, you’re in something of a position of power, which is why being hit on can often be less uncomfortable or threatening than it is in regular life.

But recently, Jamie saw the ugly side of being hit on at work when a patron ordered some drinks and offered her a large tip in exchange for her number, but then gave her no tip at all when she declined to hand over her digits. She told me her female co-worker later said that’s “the oldest bartending trick in the book” and that she should have taken the tip and offered a fake number instead, which would have reversed the power dynamic yet again.

It seems that being hit on at work in the hospitality industry is different for men and women. Even when I was talking to my friends, the girls all had a lot to say, and indeed a lot to complain about. My friend Dave, who bartends in Bushwick, merely told me, when asked how he felt when girls hit on him at work, “It’s awesome.”

Jamie’s opinion was slightly different. “Women who hit on male bartenders, in my experience, are very rarely overtly sexual in their comments,” she says. “The interaction seems to be based more on a pattern of call-and-response, where the woman will start off being slightly flirtatious and, if the male bartender reciprocates, she will very gradually become more forthright in her advances.”

My friend Connie used to work at a Starbucks when she was in college, and sums up the dilemma of hitting on and being hit on in the service industry quite nicely. “A cute older guy handed me his empty coffee cup and asked me to write my number on it. Very smooth,” she says. “I think timing is everything: you can nicely chat up your coffee shop girl every day with your order because you think she’s cute. You can get to know your local bartender with time. You can make them not the ‘coffee shop girl’ or ‘bartender’ but a real person with a real name.”

The reality is, working in the service industry, the lines between work and play do become blurred. When your bartender is doing shots with you at 2am, there’s definitely element of friendship forming, even if it’s with a brand new bartender you’ve never met before. Over the course of your evening whoever is serving you, in whatever context, is going to be the one constant in a night full of variables. And it seems that most servers agree: as long as the person hitting on you while you’re working is attractive and not pushy, there’s no harm in a bit of workplace flirtation.