Sloshed: How to Drink on a First Date

Try not to go overboard.
Try not to go overboard. Photo: Hulton Archive

To celebrate the release of Matthew Latkiewicz’s new book, You Suck at Drinking, which has its origins in Grub Street’s own “Sloshed” column and officially comes out next week, we’re dusting off the Sloshed tag and excerpting a passage. Here now: Everything you should keep in mind as you order drinks while wading into the murky waters of the 21st century dating pool.

So you are on a first date! Congratulations! Alongside selecting your outfit and making sure you don’t have spinach in your teeth, choosing your drink can be one of the most important aspects of a first date. It helps set the mood and establish your personality, and can be called upon to smooth over any awkwardness.

To properly deploy alcohol on your first date, you consider three things:

1. Choose a drinking style appropriate to how well you know the person.
2. Choose a drinking style that showcases the vibe you want to give off.
3. Avoid and/or handle date emergencies with the correct drinking maneuver.

With those three pieces in place, you will surely have success.


We have been friends for a while.
Challenge: This is the easiest situation to predict and plan for. If you have been friends for a while, you most likely have drunk alcohol with him or her before. Your date may have even already seen you inebriated. It’s also possible you made out at a party while inebriated and are now going out for a first date. For the date, you may want to employ — or deploy — alcohol to foster a more-than-friends feeling, but you must be careful when doing this! Many first dates have been taken down by a poorly timed bottle of champagne. You wouldn’t propose marriage on a first date, would you? So why would you order champagne and freak everyone out?

Drinking Strategy: Choose a drinking establishment that has a laid-back romantic vibe. Avoid candles, tablecloths, places with multiple wine glasses on the table. Avoid dinner entirely, I say. Look for something outside, preferably overlooking water. A rooftop bar could work, but again: Be careful it doesn’t feel capital-R Romantic. This is important: Get the same drink and just keep ordering it. Don’t make those drinks beer. If it must be wine, order it by the bottle. Mojitos or other laid-back cocktails would be just about perfect.

Not that well. We’ve met once or twice and exchanged numbers.
Challenge: You need to confirm that the early flirtation and number exchanging were a good idea.

Drinking Strategy: Order your absolute favorite drink and see how your date reacts. Nothing showcases a Drinker’s personality better than his or her favorite drink.

Not well. But I know a lot about him or her from the Internet, including our match percentage.
Challenge: All right, Drinkers, be careful. While Internet dating has been truly wonderful for many, many people, it presents a whole new kind of problem: thinking you know the person better than you actually do. Before the year 2000 you wouldn’t have gone on a first date having seen multiple pictures of someone; or having a very good idea of the kind of books your date likes; or knowing your date’s feelings on shellfish; and/or being aware at all of the most private thing your date is willing to share.* The Internet provides a false sense of closeness that can cause Drinkers to let down their guard. Even if your match percentage is high, remember, you kinda lied on your online dating profile, so … you know . . .

Drinking Strategy: Just as the Internet can make you feel overly familiar with someone, drinking can make you not care how familiar you are with that someone. It is a dangerous combination. Internet dating must be handled with caution by Drinkers. Start slowly, and don’t be overly familiar about what your date may like or doesn’t like vis-à-vis drinks. Order one drink and hold off on the second one until you answer the question: Do I want to stay here, or do I want to leave? If done correctly, a Drinker can expect that the slow and steady application of alcohol will allow the cold, false (but also probably weirdly accurate) computerized compatibility to blossom into actual human, flushed-cheek compatibility. Think of the alcohol as the water to the seed of algorithmic connection.

You know nothing in advance. This is truly a blind date.
Challenge: A quick and clear understanding of whether this is going to work.

Drinking Strategy: Ask if you can bring your date a drink. If the response is, “No, I’m all right,” then go to the bar and order a shot of whiskey. Drink it, and then leave. If your date says, “Yeah, bring me a …” then bring it and see how it goes.

Next choose the drink that will help you project the vibe you are going for. Like your outfit, your drink choice gives off a strong first impression, so make sure it is the impression you want to make.

*Warning: A lot of people trying to be funny and fun end up ordering drinks that are wacky and sad, like a Sex on the Beach. Don’t do this. The more crazy a drink’s
*Warning: A lot of people trying to be funny and fun end up ordering drinks that are wacky and sad, like a Sex on the Beach. Don’t do this. The more crazy a drink’s

The above strategies form the foundation of your first date. Below are ways to handle specific situations that may arise. Simply layer them atop the foundation, and the date will be delivered safely to its correct conclusion.

Your date is boring you.
Be gracious and continue to ask questions. A Drinker is always gracious and always asks questions. It is one night out of your life. If you know this is going nowhere, buy more drinks and enjoy your evening.

You are boring your date.
If you realize you are boring your date, you are already miles ahead of most boring people. Use that awareness to stop being boring. Stop your story, say, “You know what? I am boring myself, here.” Then ask: “Have you ever had absinthe?” You will immediately cease being boring forever.

Your date asks your opinion about a topic with which you are unfamiliar.
Drinkers never pretend to be something they are not. If asked directly about something you have no real knowledge of — the political intricacies of the Israeli-Palestinian relationship, say, or Stanley Kubrick’s early work — don’t feign knowledge. Instead, pick up your drink, hold it in front of you, and say, “I actually don’t know much about that. What should I know?” And then take a sip while keeping eye contact. The sip communicates that you are done speaking; the sip plus eye contact communicates this is a good conversation, and I find you interesting.
NOTE: A Drinker always strives to find the other person interesting.

You just did something embarrassing.
If it was not drink-related: Smile, accept it, apologize, wave self-deprecatingly if others are clapping. Go back to sipping your drink. Sipping will show that you are in at least some control.
If it was drink-related, you don’t care, do you?

You tell what you think is a funny story, and it falls totally flat.
The worst thing you can do in this situation is take a sip from your drink during the silence. It will only punctuate the silence following your dumb story. Instead, utilize the technique made famous during the 1990s alt-comedy boom: Fill the silence with a meta-joke about your bad joke. Something simple like, “Note to self: Never tell that story again,” while pretending to write on a reporter’s notepad. With the silence broken, quickly follow up with, “I’m going to get another drink, you want one?” Regardless of whether your date wants one, or whether you even need one, go to the bar. This will cause a natural transition and give you time to think of a question to ask. When you return with the drinks, ask your question immediately — put the ball in your date’s court.

You are told that you remind your date of his or her mother or father.
Ask what his or her mother or father drank, and then order that.

*Of course, yes, there are cases of pen pals falling in love over letters … Oh wait: NO, THERE ARE NOT.

How to Drink on a First Date