How to handle who pays on a first date. I hate when the check comes and it’s awkward. Am I expected to pay because I’m the guy? Does that depend on the girl? Is it who asked the other out? 50/50 because I support feminism? Should she pay? Is it based on who makes more? Not that that conversation always comes up but if one person is between jobs or something obvious? Fuck if I know. I seem to pick whatever answer is most likely to offend my date.

And who’s job is it to plan the first date? I feel like girls expect the guy to do it.

Well, since not every man is looking to date a woman and vice versa, we can’t really say ‘the man should pay’ or ‘the man should plan the date’ right? Plus, not everyone identifies as male or female.

Here’s the TL:DR: everyone should just assume they are paying their own way, and whomever does the asking should do the planning.

Longer version:

Who should pay?
When I was dating (I’m a woman; I’ve only dated men) I liked to pay for my share on a date in case the dude was a creeper and somehow thought him paying for my tacos and margarita meant something was owed him. That’s obviously bullshit any way you look at it, but still, I wanted to make it clear that we were acquaintances just getting to know one another, same as if I was hanging out with a new friend for the first time. If a guy insisted on paying I’d usually let him; sometimes I insisted on paying. I certainly didn’t judge him negatively if he wanted to split the tab.

The main exception to this is if you want to go somewhere fancier than, say, your average restaurant that takes — but doesn’t require — a reservation. If the date is going to run them more than a typical night out with their friends, it’s a good idea to make them aware so they can decline if it’s too expensive. Same if you are offering to go somewhere like a sporting event* or Broadway show. Not everyone can drop $100 on date night, so if that’s what you really want to do, I suggest saying outright that you have two tickets and would like to take them. Then it’s understood that the evening is on you.

It’s possible you’ll run into someone who expects you to pay regardless. In the scenario you describe above, if you ask out a woman and she expects you to pay, it’s up to you to make of it what you want. She may go by the idea that the person who does the inviting does the paying. That’s not my style, but it’s not an entirely jerk move. At the same time, she may also be signaling that she’s more into ‘traditional’ gender roles. Who knows; it will probably take more than one date to suss that out.

One last thought on paying: If you literally cannot afford anything other than a couple of drinks, ask her to meet for coffee in the park or some other public spot. You can talk, get to know each other, and not be worried that come bill time you’ll have to overdraw your checking account.

Who makes the plans?
As far as setting up the date goes, default to whomever initiated the meet-up. If you asked someone out, you’re responsible for figuring out what you’ll be doing. The person you ask out should be up front if they have any deal breakers (a seafood place is a bad option for someone violently allergic to all shellfish), but beyond that, you want to hang out, you pick the place.

If the person you’re going to go on a date with invited you but insists on you setting it up, I don’t think that’s a jerk move either. It could mean they are just tired of coming up with the plans; it could also mean that they’re interested in learning what you like to do so want to give you the chance to set something up. Like many things in dating (and in life), it’s a bit of a crapshoot, so don’t read too much into it. Just pick a place and go.

*Ask me about my brutal first date to a pre-season NFL game. This was before texting, so to get advice from my sister I had to call her from a bathroom stall. Good times.