Why You Need A Plan on the First Date (but Why That Plan Doesn’t Matter)

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You’re going on a date. The hard part is over: you asked, they said yes. Or, they asked, you said yes. Or, you both kind of mumbled at each other until you reached the mutual conclusion that yes, you’d like to see each other again. Awesome. Now all you have to do is figure out what to do. A bar? A restaurant? A show? Which bar? Which restaurant? Which show?

Here is the secret. It fundamentally does not matter. What matters is that you pick something, anything. By proposing a plan — which, again, can be literally any plan — you are showing you are a person who can conceive an idea, communicate that idea, and also then execute that idea. It doesn’t even have to be a particularly good idea. The specifics, I would argue, are totally incidental. What is not incidental, though, is your ability to suggest an activity, and then stand by this activity. “Oh, let’s go to this place at this time,” you say, and then you do that. This is so basic, a preliminary tenant of being a fun, competent, single adult, the kind of adult who does not make getting a drink into a 24 text message affair. Also, this has taken me years to figure out.

I used to be the queen of I-don’t-know-what-do-you-think, a misguided attempt to seem flexible and solicitous and generally “easy-going” and “low-maintenance” and all kinds of other adjectives applied to women in shampoo commercials. And then, while listening to myself and a friend try to negotiate the odyssey that is lunch, I realized: this shit is annoying. It is annoying in a platonic context, and it is real annoying in a dating context. When you don’t propose a basic idea you’re putting the entire burden of your date on the other person. Presumably, you like that person, which is why you proposed going on a date with them in the first place. Don’t do that to them — it’s not nice, and it’s certainly not sexy. You know what is sexy? Plans. If you do the asking, you do the planning. That’s just the rules.

On some level, being the one to suggest a plan is scary. What if it’s a dumb plan? What if that place you suggest is a dumb place? What if your date thinks you’re a dumb person, for suggesting such a dumb plan at a dumb place? But that is exactly why it’s important to do it: you’re taking a risk. You’re not hedging. You’re not suggesting “maybe a drink somewhere?” — you’re going out on a limb and suggesting a specific somewhere to have a specific drink. That is confidence right there. You are basically Don Draper, but in a gender-neutral, non-gross sort of way.

But — and I cannot stress this enough — the plan itself does not matter. The point of having a plan is to show that you’re capable of having and expressing coherent thoughts, and to take the pressure off of your date. That’s it, period. That is all your plan has to do. It does not have to be perfect. It does not have to be brilliant, novel, inspired, hilarious, or completely original. Yes, it should be thoughtful — thoughtful is good. If you know your date-to-be is into classical music and also vegan food, and you have discovered that the Philharmonic is playing a secret concert that just happens to be right near a stellar vegan restaurant, then fantastic and you win. But if the best you can do is suggest a specific Thai restaurant in a specific place at a specific time, that is totally fine, in my book. The point is to suggest something.

Once, a guy took me to a Broadway play on a first date, and then we had expensive drinks I couldn’t afford. That was good. Good job, guy. Another time, a guy took me to an anarchist collective to see a documentary about drag performance and eat a chocolate cake I later learned had been retrieved from a dumpster. That was also good! So was the time another guy invited me to a vegetarian café on a Wednesday and we split a burrito — that date, probably, was the best date of my life. And it was a burrito.

None of those dates were notable because of what we did (see also: burrito). They were notable because I liked the person I was with. That’s it. The people mattered. The activities were just backdrops. Good backdrops, but still: backdrops. The actually-important things — the talking, the chemistry — could have happened doing almost anything. But they couldn’t have happened doing nothing. And that’s the key. A successful date needs a plan, but that’s all it needs: a plan. Not even a great plan. Just an okay, totally serviceable plan. Because the best plans? They’re the ones that exist.