Do you offer, insist, or just skip right past picking-up the tab on dates?
Ahhh, that. Who should pay on a first date? When the register screen flips around, or the check gets dropped on the table. As if the early days of dating don’t produce enough awkward moments, throw in the who pays part and let’s be real . . . it can get a little weird. But, I’m here to tell you that it doesn’t have to!
This topic comes up sooo often, and some of you have some strong feelings about it. First of all, you do you, girl, this is just my take on it. And, after *a lot* of trial and error in this department, here’s what I’ve found works best.
In short, I want him to pay. Hold on, let me walk this out…
Sure, I’m a grown woman with a career that has a decent income attached to it – I can buy my own stuff (especially if it’s just a few bucks for coffee). However, that is not the point. I like me some chivalry! #sorrynotsorry. Here’s the thing though, it’s not chivalry if the courteous act is demanded by the receiving party.

So, what this actually means is: I want him to want to pay.
I love it when a man chooses to treat me, but I don’t want him thinking that I expect him to buy time with me. Yup, that’s really what it comes down to…seeing what he wants to do. The value is in his approach and thoughtfulness. Without that part of it, him picking up the tab means I’m just spending his money. That’s fine and all, except for the fact that it tells me absolutely nothing about him. I’m much more interested in what he does with the opportunity, as opposed to just whether he can cover the cost of my cosmopolitan.
So, on a practical level, how do we keep the door open on the choice factor? There’s no perfect system, but I try to make it known that I’m willing to pay my way. Usually all it takes is me reaching for my purse. Many guys notice immediately, and will not even hesitate to stop me. If my card somehow makes it out of my wallet, there’s still plenty of chance for him to graciously decline. I love hearing some version of: “I would really like to get this.” It tells me something. Something good.
So who should pay on a first date? In my view, chivalry is a choice, and you deserve someone who chooses to treat you…and treat you well, darling.
Want more dating content? Check out this blog on a man’s perspective on dating!
