Dates and paying bill

[Anonymous]

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]

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

[Anonymous]

You sound high maintenance.

[Anonymous]

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.

Ugh this would bother me A LOT.

But yeah, there's something wrong with him if he's 41 and never had a relationship longer than 8 months. He sounds unromantic and ungenerous. I'd dump him.

[Anonymous]

He sounds like a loser

[Anonymous]

He's 41 and never had a long term relationship? Um there's a reason why and other women have figured it out. Move on.

[Anonymous]

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.

This relationship has expired. He is only dating you for the sex and feels he has already paid enough for you to keep putting out. At a certain point he thinks the initial courtship ritual is over and it’s time you pull your own weight. You meanwhile want someone who will always pay and presumably who will always support you going forward. You have different goals.

[Anonymous]

Anonymous wrote:You sound high maintenance.

Disagree. Her feelings sound justified.
-a man

[Anonymous]

I mean burgers and beer has to be what, $50? And he is squawking at paying that? This guy is a tool. This wasn’t some fine dining experience that you used him for. I would move on.

[Anonymous]

Yes it think it’s nitpicky to split it like that. If you like him otherwise I would talk to him about it and be honest. He can either step up a bit financially if he thinks your worth it. If he doesn’t then you are not compatible.

[Anonymous]

Move on.

[Anonymous]

Fwiw food at the ballpark likely cost more than the tickets…

Thing is you opened the door on the money thing. The “just the tip” thing was likely a clumsy attempt at sexual innuendo. But from the perspective of a man, since you offered to pay something he had to decide whether to say no he’s got it covered or respect what he perceives as a genuine offer to contribute equitably.

You don’t exactly sound head over heels with this guy, FWIW.

Good luck finding someone to take care of you. The man is the plan, I take it?

[Anonymous]

If you’re 8-9 dates in, I think it’s fair for you to be sharing the expenses of dating by this point (and I am a woman who likes the man to pay for the first 1-3 dates). But splitting bills is awkward. He should pay for the things he plans and initiates and vice versa - that way you can each control your expenses according to what you can afford.

[Anonymous]

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

This

[Anonymous]

Talk about counting beans… you two better go separate ways. Both pathetic.