Dating Conundrum: Dinner vs. Drinks

Dating Conundrum: Dinner vs. Drinks

Picture this: You have a date with someone you’re excited about. But, it is early days. You are not yet acquainted with their snoring habits, their siblings’ names, or how they take their coffee.

​This is where I recently found myself, ​venturing forth to connect with a relative stranger in the least awkward way possible… ​

Yes, gentle readers, I am dating. That is a thing that’s happening. Since joining Tinder entering the dating landscape, I have learned many things. Chief among them: Before you can think about donning sweatpants in tandem, you have to trudge through a whole lot of awkward.

First dates are riddled with questions. What do you wear? What do you say? Will your date react negatively to your new purse? Last but not least, there is a question that divides the masses: Which do you prefer — dinner or drinks?

“When I was dating, I always preferred dinner​ dates​,” Joanna told me. “I liked knowing how long it was going to take. Plus, at dinner, you can talk about the menu, talk about the waiter, there’s a natural rhythm. A restaurant is just nice.”

To which I say, no.

In these casual times in which we live, I ALWAYS prefer drinks. Let’s not break bread until I know that I like you.

Dinner is awkward — anything that involves chewing ​in the proximity of​ a​n unfamiliar human​ is probably best avoided. (Especially if it’s sushi, where the inevitable question of “Can I fit this whole ​crazy crab roll​ in my mouth?” leads to prolonged ​chomping​​ and staring.) Also​, you know that horribly awkward moment when your server comes to the table and presents you with the list of specials? ​And you think to yourself, “Totally an actor. Swordfish is not that exciting,” then proceed to immediately forget everything he just said? These things do not happen when you meet for a drink.

​It could also be that my​ best dates have, invariably, been drink dates. ​I like knowing that the person I’m with can shoot the breeze in a totally unstructured environment. In my experience, the easier the flow, the better the whole relationship is going to fare. I don’t want to be distracted by the proper use of silverware. I want to get lost in conversation, wondering which is putting me more at ease: my drink, or my date.

My favorite date of all time — ​indeed, the very date I alluded to earlier, which happened last week — transpired at a gross dive bar not far from my apartment. The unpretentious surroundings and slow, meandering vibe led to a​ ​relaxed experience. No one interrupted to ask how everything was going or if we’d like to see the dessert menu. ​In the glow of a decrepit jukebox, w​e did, in fact, talk all night.

O​n our ​next​ date, we​’ll be going to dinner.​ ​

​Daters of the world, what say you​? Do you vote dinner or drinks?

P.S. An awesome dating tip and how long do you wait to sleep with someone?

​(Illustration by Alessandra Olanow for Cup of Jo.)

  1. Oliver says...

    Sorry, but how about neither?

    I can think of about a million better things to do with someone than go through a Wall Cleaver (Leave It To Beaver) restaurant date. I drink about 4 beers a year, and even if I drank more, meeting in a bar with all of the cacaphony is an even worse place.


    I’d rather go for a walk or meet at a party or some other kind of event. Then again, I can’t imagine arranging to go on a date with someone I haven’t already met before. Online dating is just plain weird, and I figure I can meet people on my own and don’t need someone’s help to be set up for blind dates. Ugh.

    Meet people by doing things that interest you. On the chairlift at a ski area. An art museum. In a group of 15 kayakers. At a college class you’re taking just for the fun of it, long after you’ve graduated.

  2. Charlotte says...

    I think a drink date is fine if the man isn’t going to try kiss you as you leave after spending only a few hours with you. I’ve had this happen to me, it was a tad awkward. I’d much rather an activity date though, then followed by a drink. A solo drink date can feel forced, it can be difficult to find conversation whereas I find activity dates tend to lessen nerves, be a lot more fun! I think a lunch/dinner date shows the guy is more serious, not tight with his money and hopefully not just looking for one thing. So, I vote dinner date above all!

  3. I prefer drinks especially if you aren’t sure if you’ll have chemistry. But I also like an opportunity to talk to him when we aren’t drinking as things progress – so those dates would be something like mini golf or a getting coffee. Dating seems really tough these days.

    x Tali

  4. Nicki says...

    As my dating history will show, I have been on MAAAAAAANY first dates: of the drinks, dinner, coffee and even the lunch/brunch variety! But the best first date I had was a very long, leisurely one with my now boyfriend: Smorgasburg! Yes, there was food, but there were NO WAITERS, the dessert was awesome (mango with sticky rice!), it involved being outside and the people watching was fantastic! Basically, I’m saying I like activities better… but of course drinks is always the easiest to have one and get out of there if the interest isn’t there or obviously keep the night going if you feel like it. :)

  5. casual dinner at not so trendy spot, earlier part of the evening if possible. if/in case things dont go well, know where your good friend or two (or a few) will be at that evening. mine “happened” to be rather near by … in my twenties, that worked out really well if a plan C was needed. as in C ya later.

  6. I absolutely agree with both drinks AND an activity. On my first date with my boyfriend we walked my dog to the park, snuck craft beers, and spent hours chatting on a blanket. That turned into another drink on my porch which turned into carry out on my sofa. He moved in two months later. :)

  7. MJ says...

    Caroline, just curious what you consider a good “first date” cocktail to order? There are so many choices and I never know what to order…thx and hope your dinner date goes well!

  8. I vote for brunch! I think having a date during the day is so much more relaxing and fun and to be honest, when husband removed the mini flag from his burger and stuck it on top of my food instead, I knew I had a good deal because that to me was just sweet. Maybe I like to romanticise things haha!