Let’s get better at planning dates

Based on how many people are finding this site by searching “I suck at planning dates”, it’s safe to say that for many people, date planning doesn’t come naturally. And why would it? Dating is kind of weird.

Think about what planning a date actually means. You’re planning a social event with someone who is very likely, a relative stranger to you. You’ve got a vague idea of what their interests might be, but it’s not like planning a social outing with friends where you know their likes and dislikes. On top of trying to impress them with your date planning, you also are using your meeting as an opportunity to gauge romantic interest and viability, PLUS, maybe you want to impress them. Dates can feel like a weird mix of social outing with friends, networking event, and job interview.

It’s okay if you suck at planning dates, because date planning sort of sucks in general. But, just because you currently suck at planning dates doesn’t mean you can’t get better at it.

Be Decisive

I think the first step to getting better at date planning is best summed up with the word: Decisiveness. You need to either be decisive about planning the date itself, or give decisive answers when given options if you’ve taken the back seat on date planning. If you’re planning a date, be decisive with your suggestions and use language that sounds firm. Instead of saying, “well, we could do this, or that, I don’t care it’s up to you”, use language that sounds more like this “Let’s go here, and do this, on this day”.

If you’re taking the back seat to date planning, you need to give decisive answers about ideas proposed to you. If you like a date idea, say it in clear language. If you don’t like a date idea, say it in clear language. If you decide that a date idea is bad, you either need to tell the person planning the date why you don’t want to do it so that they can propose something you would want to do, or make a suggestion instead. If someone says let’s go to Generic Irish Sports bar for our date” and you don’t want to do that because you don’t want to go to a bar with TVs in it for a first date, be clear about that. If you like part of a date idea, be upfront about that. “I like the idea of getting drinks for our first date, but not in a sports bar. Maybe we could go somewhere without TVs instead?”.


Cater your date to their preferences.

People tend to have a good time when they do things that they enjoy. So, why not plan a date that incorporates someone’s preferences or interests into a date? Let’s say that you’re going on a date with someone who really loves a certain design aesthetic, like Art Deco. Knowing that, you could plan a date at a venue with an Art Deco theme, (if you’re in NYC, a place like the Flatiron Lounge would be a safe bet). If you know someone is into fancy cocktails, plan a date around that. Are they a Oenophile? Take them to a place with a nice wine selection. It’s really not that hard to do. Everyone has a thing they’re interested in, and you can find a way to join that into a date if you give it a little thought. Or a quick web search.

Don’t plan a date you think will be bad

Sure, you should cater your date to the preferences of the person you’re dating, but you should never, ever, plan a date that you won’t enjoy. Feel free to compromise when it comes to things you don’t feel are important, but if the date venue, amount of travel, or the activity you’ll be doing on the date sounds terrible to you, don’t go on that date.

There was a time in my life where I’d agree to any date, no matter how inconvenient it was to get to, or how lame the date idea sounded, or how much I hated the venue.  Those dates always ended poorly because I was in a bad mood before I showed up because of how inconvenient it was to get there. The only person to blame was myself, because I could have easily declined the date and saved time, money, and my frustration. Learn from my mistakes. If you hate coffee dates (like me), don’t go on a coffee dates. I’ve been on more coffee dates than you’d think and they all sucked. Don’t travel an hour out of your way to go on a date with someone to make it convenient for your date. I’ve done that, and it always sucks, and the commute home only heightens how annoyed you’ll be. And don’t go to venues you hate. I wish I could go back and take back all the times I want to clubs or lounge-y clubs on dates because each one of those times I was miserable.

Have a Plan A, B, C, and D

I’m a big fan of having multiple date ideas for dates. Instead of getting attached to one idea, plan a couple dates. Drinks at that cocktail bar you’ve heard is pretty cool is a great date idea, but so is going to a low-key music venue. Have a few ideas at the ready, but only present one at a time. “Do you want to go to this cocktail bar I’ve heard is pretty cool?” If they say yes then, don’t present the other date ideas, save them for another date. If they say no, present your Plan B. If yes, save your ideas. If no, Plan C. And so on and so on.

Sometimes you have to collaborate on date planning

Though, at some point, you have to know when to ask for input. If you’ve floated 4 different date ideas and have gotten a No for each one, maybe you need to take a more collaborative approach to date planning. There is a certain amount of romance when it comes to one person taking the lead on date planning, but if you’re so off-the-mark that you can’t get a yes, you need to push for a more collaborative approach to date planning. If you’ve made the decision to take the lead on date planning, but can’t seem to make progress, there isn’t anything wrong with saying “Is there something you want to do?” or “did you have something in mind?”.

Some people like to passive aggressively plan dates by not taking the lead, shutting down all your ideas, then giving you their ideas for what they actually want to do. It’s an annoying song-and-dance but  people do it. If you feel like that’s happening, ask to collaborate.

Okay, here are two quick pieces of advice, that have less to do with date planning and more to do with date enjoyment:

Leave bad dates early. If a date is going bad, and I mean really bad, don’t stay out of some vague sense of social obligation. Your time is precious.

Split the bill if you want to. This might be controversial, but here’s what I believe about dating, and I think it should be applied equally:

  1. You shouldn’t do things just because of societal/cultural expectations
  2. Everyone should be able to pay for half of whatever date they go on
  3. Expectations that haven’t been discussed and mutually agreed upon are not valid

I don’t think is fair to assume that because of your gender and sexual orientation you have to pay in full for a dates, the same way that it’s unfair to expect sex after a certain amount of dates or money spent. That said, you should also be aware of what this might signal to the people you date. Personally, I would never not pay for a first date with someone I was interested in…but I’d definitely split the bill after a terrible first date.

One last piece of advice. When it comes to date planning, and dating in general, just try to make the most of what you’re doing. The goal is to go out, find what you’re looking for, and hopefully, enjoy it. So, if you take nothing else from my advice, try to plan dates that at least, will be fun for you.

Good Luck Out There.

Also published on Medium.