How Many Drinks Can You Order on a First Date?

bartender igniting a cocktail creating a flame effect
How Many Drinks Can You Order on a First Date? Mistey Nguyen

The biggest date night of the season—Valentine’s Day—is here. And, in preparation, friends and colleagues alike have burdened me with questions about what behaviors at the bar might split the difference between finding your soulmate and having the worst hangxiety of your life. For instance, what cocktails best impress a date? Which immediately put up a red flag? How many can you toss back on a first meet-up?

I stopped into the Internet-dubbed “cutest date spot” in New York City's East Village, Romeo's, to gather answers. Romeo's is a retro throwback bar with experimental cocktails. Hot pink neon lights inside bathe all the patrons in a romantic glow, and there’s always a John Hughes or John Woo movie playing from the projector on the wall. (You never have to worry about an awkward silence, which makes it perfect for a first date.) The menu boasts inventive twists on classic cocktails, like a cucumber gin and tonic and a pistachio Mai Tai. There's also comfort food, like hot dogs and pizza bagels, always available if your date isn't going well.

Co-owner and Beverage Director Evan Hawkins, worked hard to curate the ideal date night vibes. Hawkins is somewhat of a master when it comes to vibes, having years of experience under his belt working at other New York City mainstays like Mother's Ruin, Broken Shaker, and Goodnight Sonny. Not to mention, he met his wife, Sara Hawkins, while he was working behind the bar. Now, they preside over Romeo's (Sara has dubbed herself the "spiritual house mom" and I couldn't think of two people better suited to my fielding my queries. I turned to the sage-ologists (sages slash mixologists, I just made that up) to ask the profound questions about love and drinking. This conversation has been edited for clarity and length.


ESQUIRE: How did you and your wife meet?

EVAN HAWKINS: We met in Miami when I was down there doing a popup at Sweet Liberty. She had been hired as the brand ambassador for St-Germaine; we were doing a tiki thing, and they made her come to the bar for a drink. She wanted to grab a St-Germain drink, and I was like, "I can't make you that. I'm literally doing a popup, and we only have three drinks. I'm sorry." And then when I got back to New York, I was working at four different places, and she was my St-Germain rep at every single place. I finally asked her out to a movie. We went to the Alamo Drafthouse and saw two movies back to back. We kissed on the escalator and the rest is history.

romeo cocktail bar
Romeo’s neon light bathed interior. Noah Fecks

How did you curate a romantic vibe at Romeo’s?

Most people are building bars wrong. They build bars for dudes. I was like, "why are we building bars for dudes?" I don't give a fuck if dudes show up. If women show up, and they feel safe, then the dudes will come later. I thought we needed to appeal to a wider audience. It was a two-prong approach of threading the needle between both masculine and feminine. So that women show up, and they're on a date, they feel very comfortable. But then when a man is there there's just enough masculine touches that they don't feel like it's an overtly feminine space. We're trying to make it comfortable for everybody.

What's a romantic cocktail to order to impress your date ?

A Cosmopolitan. It's got the romantic pink color. And it's so simple and easy to drink. Our Cosmopolitan is a little different. We use Combier liqueur, and process down fresh cranberries with sugar, and orange juice. We basically make a cranberry cordial. Then we add orange oil, and we flame it on top. So, it's a wow moment when you order it. It's impressive.

Or you could start with a high ball. They're bubbly, a little bit of booze, with a good range of flavors. We have a couple on draft like a mezcal apple cinnamon, cucumber gin and tonic, and a toasted coconut Moscow Mule. You need to start light and then go for a gradual build up in ABV.

Can you tell how a date is going by what cocktails they're ordering?

Yes, and I know that when a certain cocktail is ordered that this date is going to turn the fuck up. As soon as it switches over to espresso martinis, that date is going off. They'll start with a beer, maybe a glass of wine or Aperol spritz. And then all of a sudden, if it switches to espresso martinis, I know this date is a success and they are going somewhere afterwards. And when I see that they start off with a wine or a beer, I know they're pros, and they're pacing themselves.

cocktail bar
No awkward silences here. Just talk about the 80s film that’s playing on the wall. Noah Feck

What’s a red flag drink order?

That would be if they start off hot, like right off the bat with a Negroni or three fingers of Scotch. That's a red flag. You should get out. This date is about to get wild, because you are going to get loose real quick. It's a first date, and that one Negroni isn't just one. It's always two Negronis. You're going to have a second drink. And all of a sudden, you have six ounces of pure alcohol inside you.

How many drinks is the max you should have on a first date?

Three, and I'll tell you why. For me, it could be six, but I'm an insane human, and I'm in this industry. I noticed when I was single, I had to pace myself, because it would destroy my date. They're trying to keep pace with me, and they shouldn't. I learned a long time ago that on a first date you have to slow it down, because you're trying to get to know this person. Getting ripped right off the bat is not the move. Trust me, you don't know what you look like. From my point of view behind the bar, you look like someone who has had three Negronis.

Have you seen any love connections being made at Romeo's?

I've seen a lot of regulars. There a guy that literally lives three doors down from us, and he's probably brought I don't know, a dozen dates in. None have worked out yet. But on the other hand, there was a couple that got engaged right after they came to Romeo's. They got engaged after we opened last December, and they just came back in recently to celebrate their one year anniversary.

Do you have tips for how to pick someone up at a bar?

It's tough to approach a stranger in this day and age. But we can get pretty busy, so my tip is if you see someone you like, you can bump into them. Read their temperature, see if they're open to talk. Then just say hi to them. You don't need a pickup line, or an ice breaker. Just say hello.

You Might Also Like