How many dates have you had?

It’s understandably a topic of concern because traditionally when men pay for an expensive date early on, they feel/felt entitled to sex. That may not be the case here, but it’s not a stretch to feel uncomfortable.

Do you feel weird about it?

Who cares if he thinks you owe him sex, doesn’t mean you have to do it and it weeds out the jerks real quick. I have NEVER once in my life felt I had to spend time with someone or owed them anything because they bought me dinner. That mentality is far too out dated. I once had a friend freak out because a guy bought her a drink at a bar and she didn’t want to sleep with him. Smack head. THEN DON’T SLEEP WITH HIM!. Good lord.

Yes i did, in jest

For context: I went to a Broadway show on Tuesday night. He asked how it was. I told him it was great, but joked that after seeing Hamilton earlier this year, everything seems like a high school production by comparison. (Truth.) Which led to me telling him that Hamilton was SO good that I now enter the lottery on a regular basis hoping to go back even though I’m not a theater person and had been rolling my eyes at the hype before seeing it. Which led to something along the lines of, “Oh, I didn’t know it was still in town. We could go see it together — my treat.” It occurs to me that he may not even know how expensive tickets are. When I went, I was kinda stunned by just how much it costs — I knew it was a hot show and more expensive, but didn’t realize just how much it would be. My group paid about $200 per person for mezzanine seats that were just okay. The cheap tickets (obstructed views in the mezzanine and balcony) were maybe $175.

It did make me feel a little bit weird because I think the first 2-3 months or so of dating are deciding if you want to keep dating. I’d feel guilty letting someone treat me to something so expensive early on before I know if I even like him, even if he can comfortably afford it and even if it’s his idea. We’ve only been out twice and haven’t even kissed yet. I actually don’t think he’s doing it hoping it’ll get him laid sooner.

And yeah, don’t tell the ladies you pee in the shower. Even if directly asked, it’s okay to lie! A little bit of mystery is good! Ha.

“This women’s lib thing has gone too far” is probably what my grandfather said in 1967 when he gave my mom the choice of secretarial school or a Christian college in the Midwest.

Anyway. When anyone – guy or gal – does something early in the dating stage that’s not typical, whether that’s suggesting a $400 date or getting pissed about something or idk getting drunk and pouring out their feelings, it makes me think like Ale suggested, they aren’t very aware. Huge deal? Of course not, but often with these people we find out later on that they’re a hot mess.

I’d still go out with him and go with the flow though.

Agree with Kate. Go out on a third date. Go with the flow. But it’s perfectly acceptable to not feel ready to do something grand and expensive like a broadway play. Keep it casual for now.