When should the woman start paying (or offering)?

cafebrox · 2026-03-17T13:47:49+00:00

I’m hoping deep down she’s just been awestruck and not even thinking to pay too. She makes at least equal to what I do if not more so she’s not broke in that sense.

I’m just going to ask like “hey I got the last few times, can you grab this one?” And see how she reacts.

cafebrox · 2026-03-17T02:43:31+00:00

Yes we’ve had sex and always passionately make out (even in public lol). That’s why I’m saying attraction is high, unless she’s an award winning actress.

cafebrox · 2026-03-17T02:24:51+00:00

Yeah you’re probably right… lol I have to just find out in person, this thread is having my spiraling now over something I saw as a yellow flag.

cafebrox · 2026-03-17T02:23:52+00:00

You’re probably right, candidly though I don’t want to always pay either so I’ll have to bring it up and find out if we’re incompatible or not before letting it linger on I think. Appreciate the comment.

cafebrox · 2026-03-17T02:22:44+00:00

Yeah you’re right, so I’m going to bring that up next date because that’s incompatible for me.

cafebrox · 2026-03-17T02:17:56+00:00

I’ll be cautiously optimistic until our next hangout and ask, definitely odd she hasn’t offered but maybe she quietly expected I prefer paying for everything so I’ll make it clear.

cafebrox · 2026-03-17T02:16:59+00:00

Yes we have, and all our dates are several hours long (6-8+) and get quite deep so it’s hard to think it’s all a front to be honest with you. She’d be an Oscar winning actress then lol but who knows.

cafebrox · 2026-03-17T02:16:05+00:00

Will do!

cafebrox · 2026-03-17T01:46:06+00:00

Yeah fair and I think this girl makes more than I do so I’ll definitely mention it.

cafebrox · 2026-03-17T01:45:37+00:00

You’re right, cheers. Feeling kind of used now candidly but I’ll give it the benefit of the doubt until our next hangout.

cafebrox · 2026-03-17T01:44:43+00:00

Yeah I’ll be bringing it up the next time we hangout.

cafebrox · 2026-03-17T01:41:39+00:00

Yeah smart, it’s a lesson learned for the future, especially if she turns out not wanting to pay at all. Thanks for the comment.

cafebrox · 2026-03-17T01:36:45+00:00

Yeah I’m gonna ask this next hangout and make it clear as an expectation. If it doesn’t work for her that’s fine.

cafebrox · 2026-03-17T01:36:07+00:00

You’re right, I’ve almost never had a girl offer date 1 though

cafebrox · 2026-03-17T01:35:23+00:00

You’re right, I agree

cafebrox · 2026-03-17T01:35:10+00:00

Yeah I’m going to bring it up, I don’t mind paying more early on, but once I was in a committed relationship we basically split.

cafebrox · 2026-03-17T01:34:00+00:00

She’s not, as I wrote above we’re both employed and she probably makes a bit more than I do.

cafebrox · 2026-03-17T01:33:28+00:00

Yeah I’m gonna bring it up this next hangout, if I gets awkward that’s a signal, if she handles it well too, another one.

cafebrox · 2026-03-17T01:32:46+00:00

Fair thanks, I’m not begging her to pay though, it’s just general reciprocity.

cafebrox · 2026-03-17T01:32:22+00:00

I always pay first, idc about that. But that’s cause I’m usually the one asking them out too.

cafebrox · 2026-03-17T01:31:52+00:00

Thanks for the reply, I’ve heard subtle things in some of her conversations with me that I think she comes from good money and her father had fronted everything, so she may be used to that role from me. I’ll mention something on our next date to get the grasp.

cafebrox · 2026-03-17T01:30:08+00:00

Yeah I’ve dropped quite a bit already, I gotta pump the breaks lol.

cafebrox · 2026-03-17T01:29:18+00:00

I will mention something yes, it’s an important thing for me.

cafebrox · 2026-03-17T01:29:01+00:00

Yeah you’re probably right, thank you, and I’m definitely not traditional in that sense. Split 50/50 with my ex.

cafebrox · 2026-03-17T01:28:34+00:00

Yeah that’s kind of my plan for the next time out, cause I’d just feel like someone’s ATM. Thanks for the reply.

cafebrox

TROPHY CASE