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.

Get more Postmodern Love ?
  • Lily

    “WHAT IS WINE!?” I scream. … Crying laughing. This is too good.

  • hearceespeak

    Amelia, this is wonderful. Absolutely wonderful.

  • Harling Ross

    CAYOOT ILLUSTRATIONS. and very funny words.

    • Amelia Diamond

      MARIA MARIA!!!

  • Surfysummer

    Yes! So funny. Thank you.. Also, my addition to this list is that if you are enjoying your date and thinking a kiss may be in order, go with a Mojito (minty breath).

    • Amelia Diamond

      I wishhhh I liked Mojitos so much more

    • Katey

      I love mojitos so so much but my worry is that if it’s a crowded bar and im the only one to order a mojito isn’t it a little rude to order a drink that takes FOREVER to make (muddling and mixing etc)?? I would love thoughts on this — I adore mojitos but I don’t want people to judge me for ordering such a complicated / labor intensive drink 🙁

      • Surfysummer

        I guess if you’re at a bar with 20+ people waiting for drinks and a flustered bartender, then maybe it would be polite to order something more simple. But besides that, it’s the bartenders job to make drinks! A nice tip is a way to show appreciation for the extra work, but I wouldn’t feel bad ordering a drink you genuinely enjoy. And even more so in a date scenario, I think men love a woman confident in what she likes to drink. 🙂

  • Helen

    Amelia! I have a first date tomorrow and I’m thinking gluhwein? Too festive? No? Okay good

    • Amelia Diamond

      WTF IS GLUHWEIN!?!?! YES!!!

      • Helen

        Hot red wine with cloves and cinnamon and orange in it! It’s like Christmas barfed in a cup

        • Aydan

          DO IT!

        • Amelia Diamond

          this would definitely make me barf in a cup, but if you can get through two of these then i second Ayden and say do it

    • Ashley Marie Perkins

      GLUHWEIN!!! My fiance is legitimately from Germany and the first time he took me to his home, we walked around the street, sipping Gluhwein from warm mugs – like actual, ceramic mugs. Just walked around the Christmas markets and got a nice, warm buzz. It was fantastic.

  • nevvvvave

    this surprisingly has never been a stressor in my life….but now it is lmao

  • hilarious. i am cracking up over here. i can’t pick a favorite line. i thought it was the champagne one then i read the cowboy part and then came band-aids. (FYI: i usually go with a moscow mule and i like when my date either somewhat copies my order or gets a whiskey or something cause i think it’s sexy and it means he has no problem with consuming hard booze on a weeknight and i can pretend to be all cute and say “i can’t smell that because it makes me want to vomit”)

    • Amelia Diamond

      oh I LOVE A MOSCOW MULE but i hate hate hate those tin mugs they serve them in!!

      • WHAT! why? cause they resemble a steel drum? how else are you supposed to achieve the perfect temperature? i refuse to put hand carved mini ice cubes into a regular glass.<— my next real housewives tag line

      • Lindsay D

        try moscow mule with tequila it is HEAVEN, you won’t even notice the cold mug

    • Kelly

      I was going to suggest a moscow mule!
      But the fail safe is usually a glass of red, if you aren’t drinking too much you’re not getting purple teeth.

      But all of this depends on where the first date is…

  • XOErica

    Ha I never heard someone describe whiskey as tasting like band-aids, but so true! I’ve gone w/whiskey sours, seems like a compromise between the toughness of whiskey, but more tasty. Or Jack + Ginger.

    • Amelia Diamond

      we just had a whiskey tasting last night and legit my mind is changed. i think i have been drinking bad whiskey.

      • scotchsux

        I dont know about whiskey, but Scotch – good or bad – ALWAYS “tastes like Band-aids.”

        ^^ Can I plz plz plagiarize your awesomely accurate description?!

  • Molly D

    Ordered 2 Stella tall boys the other night and like you said, had to pee. Getting up to go to the bathroom is its own anxiety bc it’s like “hey, you’ve been staring at my face for an hour, but welcome to what the backside of my body looks like and please judge my gait while I try to act like I’ve walked nonchalantly before”

    • Amelia Diamond

      the bathroom is a WHOLE OTHER THING MAN

      • Molly D

        including having to come back out

    • omg standing up gives me so much anxiety

    • Why is getting up so awkward??!

      • Molly D

        It’s an introduction to your physical form which let’s be real is the elephant in the room of like do I look good enough for either of us to ever want you to get to know it

        • ‘Hello, I hope you are pleased by my physical form.’

  • I’m glad I’m not the only one who associates pinot grigio with Ramona!!

    • Adrianna

      For some reason we had her wine at work once. Ironically I would describe it the same way she did when Jacque tricked her at that wine tasting party

  • Ashley Marie Perkins

    I have an entire, elaborate system that is almost too embarrassing to divulge on the internets. But it includes appropriate times for drinking beer (and which beer), and yes, I order prosecco a lot, but mostly I just order a negroni.

    • Amelia Diamond

      love a nergroni but how many can you drink in a row on a date??

      • Ashley Marie Perkins

        Depends – if it’s a dinner date, then I have one before dinner, and then order something like wine with dinner. If it’s not a dinner date, I drink slowly. 😉

  • Bekah
  • “whoa, okay, hard day on the ranch there, cowboy?”

    I don’t know how I lived live before Man Repeller.

  • tmm16

    Such accurate descriptions and this decision always goes through my head when I’m out on Tinder dates! I also fall into the category of being the girl who “gets what he’s ordering” so usually it’s beer, and yes, I usually have to pee. Also, my “drinking dates” usually go 2 ways: It lasts for 1 drink and I go home or my date and I are 5 shots deep in tequila and I’m questioning if I will be going home. So maybe the ideal drink is not one, but 3 or 4 of them?

  • Abigail

    Also as a ‘young person’ dating other ‘young people’ I always worry about price… Always feel like such a shit ordering something pricey when I know the guy is still at uni and trying to pay London rent prices 😁

  • Andrea Raymer

    this is my thought process every time i ever order drinks ever! and as someone who likes tequila i feel like people think im going to get crazy when i order it.

    this is why i go to one bar where my friend is the bartender and i make him make me things until i like something and dont feel judged for it. recent winner that i can order most places: vanilla vodka with ginger. but under pressure I might feel like I’m at a table at a bad club or in college.

    • Andrea Raymer

      also, another recent conundrum: what to order at a dive bar with a bunch of friends from church when you don’t like beer. i just got tequila and grapefruit because i like it but EVERYONE commented on it.

      • Lillian

        I am you

  • Lisa

    blueberry press with a splash of cran. sounds and tastes yummy. also, there is sipping whisky $$$ and mixing whisky $.

  • Would love to have these illustrations as posters on the wall 🙂

  • Charlotte Dallin

    I always drink gin and tonics. Now I’m paranoid.

  • Samantha

    Campari and soda to start. I have a fancy European friend who introduced me to this and though it tastes mildly medicinal, it doesn’t make me want to nap or strip. I can do two of those, and then — depending on whether or not he’s a doorknob and I need to escape — I’ll finish with a martini. (At this point in the evening, spillage goes unnoticed by both parties.)

  • rachel

    Rum and coke makes me feel 18 but also keeps me in a good caffeine-alcohol-sugar place so I’m sticking with it. Plus if there ends up being a make out sesh, who doesn’t like coke??

  • Mariana Gaviria

    moscow mule with jameson is the best drink in the world!

  • vh

    How about this? Order whatever you feel like drinking at the time.