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How to Flirt, According to a Bartender

Photo-Illustration: The Cut; Photos: Getty

There are not a lot of professions left where “being a good flirt” is a healthy and celebrated characteristic — and that’s probably a good thing. But bartenders? Well, they still get to have fun if they want to. That’s why we consider this 35-year-old bisexual bartender in Tribeca an expert. “Flirting is a life skill I was born with,” she says. “So why not convert that into a job that pays well and sometimes results in mind-blowing sex with the exact person I planned to seduce and sleep with?” She estimates that she goes on about one date a month with a customer. “I’ve never been the hottest girl at the bar, as a customer or a bartender,” she says. “And yet, I know that at any bar or party I can get anyone I want.” Here are her tips.

1. Don’t give your life story. 

I try to be low-key alluring. Just interesting and conversational enough that someone is curious about you, but still reserved enough that they need to know more. Make them wonder if you’re straight or queer; make them wonder if you’re smart or dumb; make them wonder if you’re monogamous or poly. You can show a flash of your true self, of course, but don’t reveal too much, not until they’re invested in you and you are dating.

Here’s an example: The other night I was bartending and a guy came in to have a drink before his date, which was at a restaurant nearby. He wanted to take the edge off and ordered a beer. I was like, “Let me guess … you have a first date tonight?” I just knew. Anyway, he unloaded all this shit about the perils of online dating. We laughed. We commiserated a little, just enough that he knew I was single and available-ish. But I didn’t share anything about myself, really. I intentionally held back. He doesn’t need to know that I’m looking to fall in love, that I’m worried about getting older and not having kids … hell no! This approach is the polar opposite of being desperate.

Who knows what happened on his date, but he followed me on Insta later that night and has since asked me to dinner. Boom.

2. Eye contact really works — but make it subtle. 

Rule No. 1, don’t be too aggressive with your eyes. Don’t stare! Don’t be scary! Let them catch you checking them out, then quickly look away. You’re just planting a little seed. And if you’re chatting, remember that your eyes are a reflection of your inner life, so if you’re truly engaged, it will show in your eyes.

3. Try some light touch. 

Here’s where you have to remember that straight men, specifically, are very simple creatures. If you touch their knee, they’re going to respond and they’re going to probably want to fuck you. I’m not saying that’s a good thing — these guys can be total buffoons when you’re just being friendly and they assume it means you’re gonna bang. But let’s assume this is a straight-male buffoon who you’re actually interested in. A little knee touch, mid-story, is a good move. You’re telling him about your best friend from college who made millions of dollars off her vegan skin-care line but secretly she gets drunk and eats Chick-fil-A every night, and he’s laughing. You touch his knee, like, “I know, right?” It’s like a quick brush of the leg. He’s yours after that.

If it’s a woman you’re flirting with, you can always be like, “Wait, let me fix this piece of hair” and just brush her bangs to the left a bit. Hair, ears, neck — works for me and works for most women. But be delicate and make it fast! You need to take the temperature. And by all means, if the person seems uncomfortable by being touched, even for a millisecond, apologize immediately and don’t do it again!

(In my experience, if you’re queer, you’re going to be better than most at the flirt game. You’re going to cut through the bullshit more naturally. You’re going to say, “Are you single? I think you’re really sexy.” And voilà: It’s either happening or it’s not.)

4. Don’t get too drunk, especially if it’s a first date. 

First dates are all so high stakes in this era, because the dating inventory is so big and everyone is looking for red flags. It’s like, you go on a first date not looking for a special connection but, instead, to find out what’s wrong with this person. So sadly, you have to handle a first date with precision instead of a carefree romantic approach. Which means don’t get too drunk. Don’t show all your cards. You can float some things that make you human and unique — a crossroads at work, some family drama. I personally think you can talk about exes, but don’t sound too messy.

As far as flirting, you can ask them to try your drink (“Take a sip …”); you can hint that you like sex or that sex is important to you, if that’s your truth. I was recently on a first date and said something like, “The sexual chemistry with my ex was off, and sex is really important to me.” And it was in that moment that this guy was, like, fully locked in.

5. Pick up their tab. 

If you like someone, buy them a drink or pay for their dinner. It’s simple. I can assure you, at my bar, the girls want the guys to pay for them. As would I. It’s brutally awkward when the guy asks to split the bill with the girl. With queer couples, it’s usually clear who is going to pick up the bill or they very seamlessly just split it. If you don’t have any money or you’re struggling, find a way to take that person out without it being expensive.

I once dated a struggling writer who texted, “I’ll be honest, I don’t have a lot of money right now, but I’d love to meet you on a pretty park bench and bring you a lemonade.” I went on that date. We shared a lemonade. It was wildly romantic. This was the same guy who said, mid-date, “Do you think we should get the awkward first kiss over with now? Then we don’t have to worry about it later. Also, if the kiss isn’t great, we’ll know that we should probably just be friends.” It was a totally neurotic thing to say but I personally loved it. The kiss was nice, but I wanted to be friends nonetheless … and we are still great friends!

6. No boring texts. 

I think text-flirting is pretty important to get right. It’s a balancing act. Don’t write boring texts with no meaning or innuendo, but don’t love-bomb someone or send a million eggplant emojis, either. I say make each text count. Give each text a flirtatious undertone. Emojis go a long way. There’s a big difference between writing, “See you tonight at 7!” and “See you tonight at 7” plus a pink-lips emoji. Fuck it!

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How to Flirt, According to a Bartender