My boyfriend that I just started dating is a doctor and works long hours.. He obviously is very well-off financially and expressed to me our first date that most girls take advantage of that fact, I'm also very well-off but I'm much younger than him so I'm assuming he doesn't think that, I am not nearly in his salary but don't NEED him to pay for anything , at all.. I spent the night with him last night and this morning he told me that he could just call a uber ( cab ) for me and I said OK and went back to bed, he's done this before.. I ended up just calling the uber myself and paying for it myself, I always feel weird about him paying for it because it is less than 20 dollars and I am not the type that likes to depend on people , AT ALL. So I called the uber and called him and he was like oh OK , I would've done it.." and I was like I know it's OK, blah blah bye.. I also made the bed for him, do you think he will be insulted that I paid for it or impressed that I wasn't asking him to pay?
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No I think it should reassure him that you're not trying to take advantage of him. Another idea you can throw in is alternating the bills instead of getting too 50/50 on everything. You pay one date, he pays the next. This way it's like you're doing something for each other and not looking picky on the money thing.
There are definitely girls that look for guys with money so I can definitely see why he is concerned. The job title means he is taking tons of insurance claims and that he made a good career. So girls are gonna see that and naturally call him "successful" and flock to him regardless of his character.
I don't think he'll have to worry about you like that though. Most girls who want the guys with money are easy to spot and blow their cover very fast. They'll only want dates that involve him spending lots of money, they won't spend time with him otherwise, they'll constantly bring up ways to have him "save" her financially by playing a "princess in despair" role(example: I got a ticket! OMG! How am I gonna pay this off!?"), and so on.1