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[quote=Anonymous][quote=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. [b]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. [/b]

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. 
[/quote]

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.[/quote]

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