I see a lot of back and forth about who should pick up checks on dates (in hetero dating) here’s some of my thoughts on the conversation, for reference I’m a 38 year old man:
Men, IMO, should generally pick up the first 1 to 3 checks. It’s just good manners to show a lady you’re interested in her. It can be just the first one or 2 or all 3; use your best judgment. Now, there are exceptions and situations where this may not apply. For example, if a woman suggests or requests a very expensive locale within the first couple of dates it’s absurd to expect a man to drop hundreds of a dollars on a woman he isn’t even sure is actually interested in him. Also, men, paying for a date or multiple dates means nothing. Yes, it sucks to invest in a woman who isn’t interested, unfortunately that’s dating. Do your best to pay attention to signs of whether she is actually interested or just wasting your time. And never (I mean NEVER) ask a woman to send you money after the fact. Sometimes, you just have to take your L and keep it moving.
Women, if you are interested in paying for a date, just pay for it. Don’t half-heartedly offer with no actual intention of picking up the tab. Don’t play games where you offer but don’t actually want to pay and will hold it against the man. That’s corny and immature. Take your card out and give it to the waiter, don’t sheepishly go for your purse, then pretend like you’re so taken back when a man beats you to it. Simply insist on paying if that’s what you want to do. Or better yet, so there is no confusion, at the beginning of the date, tell him the date is on you, and you will be picking up the check. Show initiative. It’s very attractive and there is no competition at the end of the date. If you come across a man who refuses to allow you to pay under any circumstances to the point that he becomes angry and moody that you would even suggest it, he is likely a misogynist and you should run away as fast as you can.