I’ve been dating someone for around 4 months. He’s quite keen (I like him but I’m not as certain yet).
I’m around 10 years younger than him and he’s recently paid off his mortgage (he chose to tell me this early on!). I have a good job but have only really just got on the property ladder, have car repayments and only just starting to pay off anything decent with my student loan. That said, I do have spare money and can afford to go away and do things. My point really is that while I am independent, like most people it’s not always easy and if something goes wrong like a boiler breakdown then it’s your usual panic situation. (Yes I am saving a little as I go before anyone latches on to that! 
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This man, lets call him Pete, has made a few comments about money that I find unusual compared with people I have dated before. I want to give all the facts so this may be relevant...I had the week before this comment mentioned that I hadn’t stayed out long for drinks with friends as I had overspent a bit last month on a trip away. It was a flippant comment, made in passing when he asked why I was home earlier than expected. Later that evening we talked about going to the cinema one weekend soon and he asked me if i could afford it. I found this comment strange? Almost like he was checking if I would be expecting him to pay, which I find very insulting! I make decent money and he can quite clearly see that I’ve set up life for myself without any help from anyone - I’m not a freeloader. And then on top of that, given he’s paid off his mortgage and likes to comment on that (fair enough he’s proud to have done it at a reasonably young age), you’d think he wouldn’t actually be bothered about forking our 15 quid on two cinema tickets IF it was the case that I couldn’t pay for it.
He’s made other similar comments, for instance I said I didn’t want to pay for a taxi back from town as I was going on holiday soon so I was happy to drive and just have one...he said ‘we’ve got to pay to meet up one way or another and it’s nice to have a drink.’ Again, rather than basically telling me I should pay for a taxi, if it matters so much just drop me off on the way back before he goes to his?!
There was also a night out very early on, date three maybe, where he wanted to take me to some bars he knew of. It was very expensive and when the bill came he said to the waiter immediately that we’d split it. Given that he’d wanted to ‘take me to these places’ where I had no say in the cost as they were new to me, I feel like he should have at least asked if that sort of place was ok before we went in, or been prepared to pay for it. I wouldn’t take a friend somewhere extremely expensive and assume they will spilt a bill with me because I had decided we would go there. It seems rude.
AIBU? He’s generally nice in all other ways but lack of generosity is a turn off for me, especially when someone is wanting to constantly express how comfortable they are and then makes these sorts of comments. I’ve no issue paying my own way (I always chose that option) but his attitude makes me so uncomfortable...