This story appears in the March 2016 issue of Playboy. Subscribe

I’ve been bartending for more than 10 years in all sorts of bars in all sorts of countries. I’ve seen pickups that have gone incredibly well and have wanted to ask the guy (or lady, for that matter) about his technique and just how he did it. Much more often, though, I’ve seen epic train wrecks, just crash-and-burn types of scenarios—the kind of thing that makes me want to hide behind my bar to avoid the shrapnel. But sometimes I can’t escape, and that’s because it’s me they’re trying to come on to. Want to pick up a bartender? Here’s the approach:

You know what’s great? Nice people. So be nice.
And be chatty. I love it when someone at my bar actually wants to chat rather than stare at his cell phone. It’s a breath of fresh air and sure to get my attention. That said, Friday night at 10:30 isn’t the time to ask me my life story.

I owe you nothing.
Sorry, but just because you’re buying a drink and tipping handsomely doesn’t mean you own me. I work in the hospitality industry. That means my job is to be nice to you and—you guessed it—serve you drinks. Nothing else.

I’m good at my job and I like it.
A lot of people in this field are here because they love it, and some have left other, more mainstream jobs to be here. Don’t assume because I sling drinks that I’m a failed actress/singer/model. Bartending is a career. If you’re trying to pick me up, you should think what I do is cool, because it is.

To my bros out there: Don’t get upset if you’re served a drink that’s pink or in a coupe glass.
That’s just being douchey. No self-respecting bartender will go home with someone who cares about something so stupid. I can drink mezcal or scotch or rye on the rocks—why can’t you enjoy that pink drink? Get rid of the outdated cocktail biases and enjoy.

Ask if you can buy me a drink. Key word here: ask.
I may not want one. And if you do buy me one, ask what I like. This goes without saying when you’re trying to pick up anyone—be it the bartender or the lady sitting next to a vacant chair. If you’re well versed in cocktails, suggest one you’ve had before and ask if I’ve ever had it or would like to try it. Do I like manhattans? Why yes, I do! Have I ever had a Bensonhurst? Maybe not. (See recipe at right—if you like the classic manhattan, ordering one of these could be good for you, or for her.)

If you have the nerve to leave your number on your receipt, you should have the nerve to tell me you’ve done so.
When you pay, say you’d love to take me out sometime and that your number is on the receipt. Don’t ask for my number. That’s awkward, and I may not want to give it.

The best thing to do is become a regular and get to know the bartender.
I’ve become good friends (and yes, scored a few dates) with guys on the other side of the bar. Generally it’s because they’ve come in again and again. It’s nice to know the bartender, and it’s nice for us to know you.

And here’s the drink I’d want you to buy (or make for) me:

The Bensonhurst


• 1½ oz. rye whiskey
• ¾ oz. dry vermouth
• ½ oz. Cynar
• ½ oz. maraschino liqueur


Stir in a pitcher filled with ice, strain into a cocktail glass and serve with a lemon twist.