Anonymous wrote:I'm a year older than you so I think I can add some generational perspective here. He's cheap for accepting your offer to pay - most men who are gentlemen would turn you down - but you are making it needlessly awkward. Venmo? It needs to be a little smoother than that. Let him pay for dinner and then you suggest a round of drinks somewhere that you can pay for.

However, I did pay for a fourth date recently and that was because he had to step outside for a work call and I thought it was tacky to just sit there with the bill in the middle of the table until he was done. And when he came back in and realized I had already paid he was mortified.

Anonymous wrote:

Anonymous wrote:Women are all about equality until they date, then they expect the man to pay.

I think more people operate under the following principle:

-- Whoever issues the initial invitation pays. Since this is typically the man, he is expected to pay.
-- As a relationship develops, the bills tend to get split proportionate to income. Usually on a reciprocal basis. This is equity, not equality, btw.

In this instance, it sounds like it's what happened. What made it painfully awkward was offering to Venmo piecemeal portions of a small bill instead of just reciprocating in some other way.

Anonymous wrote:Women are all about equality until they date, then they expect the man to pay.

Anonymous wrote:Women are all about equality until they date, then they expect the man to pay.

Anonymous wrote:Move in, for a variety of reasons.

I cannot believe he allowed you to Venmo him for the drinks. It would’ve made more sense for you to arrange the next date and treat him - but the way this went down is so awkward and just - unromantic, joy kill and off. My attraction to him would’ve completely dried up, what a tool. And no relationship at 41? Red flag.

Just break up with the guy.

Anonymous wrote:I've been going out with a guy for a little while now. He's 41 and I'm 29 if that matters. He's the oldest guy I've dated, I'm usually into guys my age. He makes more money than me (I'm guessing 3x) but he's still middle class, I'm in the low income bracket at the moment.

We have hung out maybe 8-9 times now. I always try to help out when I can when it comes to funding dates, though I'm more thrifty. I've paid for both our movie tickets on discount day, cooked dinner for him twice, etc. When he took me to a baseball game he bought tickets and I bought food. He has paid for drinks at a bar before and I thanked him and told him how much I appreciate it.

So anyways, would this situation be weird to you? He invited me out, picked out the place. He did not compliment me even though I put effort into my looks. This wouldn't normally bother me, but he did compliment the hostess on her nails.

Then we order, I order a burger and fries and so does he. No apps or anything extra. He gets a large mug beer and I do too. When the bill comes, he picks it up so I assume he's paying. I offer to cover the tip with a Venmo. He laughed at me saying "only the tip?" Then suggested I pay for the drinks and he pays for the food. I agreed and sent it to him, but I felt weird about it.

He's never had a long term serious relationship, so I keep that in the back of my mind. He hasn't had many hookups/short term ones either from what he told me (he seemed embarrassed about it). A few one night stands plus a 8 monthbrelationship. Now I'm wondering if this kind of thing is why, or if he just doesn't get the social norms because he hasn't been dating.

Anonymous wrote:

Anonymous wrote:Move on. 29 is prime dating years. Target men 28 to 34 who are well employed and not cheap.

This