the perfect date

no dressing down, no bad music unless it's funny

I used to think the perfect date was a walk through the Art Institute of Chicago and a $27 carbonara in West Loop, and I don’t know who I was kidding. The pressure of silently walking through the rooms, recognizing Edward Hopper’s Nighthawks, and immediately saying something witty is simply too high. It doesn’t matter if you already have the comment ready – “Look, that’s you and I at Burger King in twelve hours” – because, even if the date was mostly fine, it never managed to show off what I wanted to show off, or goof around the way I wanted to goof around.

When I first started dating my boyfriend, we spent a lot of uncommonly hot autumn nights making dinner together (fighting against our combined four roommates for counter space), biking to Lake Michigan, diving into the water from the Point’s limestone rocks, and after drying off, stumbling into one of Hyde Park’s dive bars. I think what made these moments so romantic in retrospect is the level of comfort we both had in these places which allowed for conversation to flow naturally, how little money we had to spend to get to know each other, and the excitement we felt about the neighborhood – which made it feel as though we were, in a sense, “going out.” These early dates set a great tenor for our relationship. 

Since then, we’ve had many kinds of “special event”-type dates: stumbling into Au Cheval on our last night in Chicago and miraculously getting a table right away, stumbling in late to the San Francisco Ballet a few minutes late but having consumed exactly the right amount of wine at a bistro a few blocks away, and, maybe best of all, stumbling into my favorite ramen place after a rainy and difficult work day. There’s so many kinds of dates you can have and so many kinds of people you can date. There’s simply too many considerations to prove the existence of the perfect date, which I tried this morning to chart for you below. 

sorry about my handwriting, my hand is covered in bandages

While this spotlights some fun dates (and truly anything on here could be plenty of fun – “basic” is no insult), it only depicts creativity and formality. To really gnaw at what makes a good date, you also have to consider:

Compatibility – what highlights something you both like? It’s not fun when only one person is excited.

Effort - Where are you in your relationship? Are you putting in enough thought? (The stories I’ve heard about this one…)

Cost - The ~magic~ you seek on dates is probably cheaper than you think, but I’m a big advocate for, every once in a while, going a little out of budget.

Intimacy - Don’t listen too much to the opinions of your friends or your coworkers at your startup who are “basically your brothers” or me, for that matter. It’s for you and your partner (or group of partners, I guess I live in the Bay Area).

While potentially helpful, this is all pretty vague and high-minded. For real-life suggestions, I asked a couple of my friends for their advice:

What’s your perfect date in 2024?

• “Going through each others instagram story history over natural wine and seeing who has shared the most infographics.” - Jonathan

• “All my best dates seem to net out at an odyssey through a city on foot — seven miles and ten hours is my sweet spot.” - Alexandra

• “I love to cook dinner and then go out to a bar, preferably with live music and dancing.” - Ben

• “Short walks on a long beach, long espressos in a small cafe, small gestures that reveal a whole lot.” - Jordan

• “Homemade mapo tofu and only hanging out once.” - Jack, whose tactics were recently featured in The New York Times

• “We split 2 mains and spend dinner deciding when and why ‘third spaces’ became so ‘zeitgeist-y.’ First one who cites ‘Bowling Alone’ has to pick up the bill.” - Charoo

• “Sneaking alcohol into a dinky indie movie theatre, watching a screening of a trashy 00’s horror and leaving far more drunk than anticipated.” - Emily

Enjoy trying these suggestions out. And when in doubt, remember: Go less commercial and more personalized. Make it high effort, but not too much that it scares her away. Create an opportunity to do something special, but don’t set expectations so high that your night can’t possibly meet them. It’s easy!

Even you can have as much fun on dates as Anna Karina