The Anxiety of Picking the Perfect Date Drink


I have never had to throw a drink in my date’s face. I’m glad there hasn’t been a reason to, and in terms of taking Michelle Obama’s We Go High Route, it’s probably not the best move. I just think it’s such a glamorous and unnecessarily dramatic “F-you” that I’d like to experience before I die. It’s like the middle finger of the 1940s. The old Hollywood Take that, ya prick! (As said in a mid-Atlantic accent.) No one dresses up anymore!

Here’s the thing. If I were to have the opportunity, no way would I have the right drink in hand. I’m excellent at first dates but terrible at ordering on-a-date drinks due to a unique type of anxiety that overtakes me the moment a waitress pops up. It is as though I’ve never heard of any of these crazy things on the menu in my whole life. “WHAT IS WINE!?” I scream. Usually, it’s as though I can’t even read.

Here’s my thought process:


I can’t do vodka soda because that will make me look like I’m trying to go out after.


No to vodka soda and a juice mixer because then I’ll feel like I’m part of a table at a bad club. Also, juice or soda with alcohol gives me college-drinking flashbacks.


Ordering champagne on a first date is rogue because like, what the fuck am I celebrating?


Prosecco is cute in theory but you can only drink from a fluted glass one of two ways: 1) really dramatically where your head tilts back to get the liquid in or 2) to avoid the dramatic pour-down-the hatch, you have to tuck your whole face back and it makes everyone look like a double-chinned turtle.


If you order the bar’s specialty cocktail, it says nothing about your personality. Plus, if things work out with you and your date, your potential future partner is going to have a much harder time identifying “your signature drink.” And that’s one of those things you’re going to want your partner to know (but he/she probably won’t because who does, which will start a fight. It’s the little things!).


A martini is classy. Here’s the thing, though: the glass is impossible to drink from without spilling. It’s as if it had been ergonomically designed not for sipping but for trouser-drenching. Ugh, and if you order your martini dirty, then you’re beholden to a “dirty” joke…I don’t know. (A martini, however, would be an excellent candidate for drink throwing.)


If I get a beer, I’ll have to pee too much.


Ramona from Real House Wives of New York ruined white wine in public for me.


Rosé gives you terrible hangovers, plus in New York City, it’s considered seasonal.


Red wine means purple teeth and falling asleep.


A margarita, my favorite, feels way too much like a summer drink.


If you order tequila on the rocks it’s like whoa, okay, hard day on the ranch there, cowboy?


Gin and tonics will give you grandpa breath.


As for the ultimate cool-ass drink to order on a date, the height of sophistication, the ultimate power move? Whiskey, either neat or on the rocks, not mixed with Coke or as a shot. My main problem here is that I think they taste like Band-Aids.

Usually what ends up happening is I panic. Order something weird. And promise myself that I’ll think this through the next time. Justttt in case I need to toss one back in the other direction.

Illustration by Maria Jia Ling Pitt; follow her on Instagram @heysuperstar.

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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