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There's a big difference between walking around almost hard in front of your gf and walking around almost nude in front of her 14 yr old daughter. I honestly wouldn't have thought to have this conversation because I would have assumed that he wouldn't dress like that in front of my child. I have children, and I've dated while I've had them, I've never had to explicitly say “hey please don't walk around in nothing but “tight” underwear in front of my daughter. It's kind of a given, or at least it should be imo.
Firstly, I don't wish to be harsh but it sounds like you both have a poor relationship with money. Maybe spending a little less would result in fewer arguments over who pays for what.
Secondly, he seems to be treating this as more of a business relationship than a romantic relationship. I've been wife my wife for 6 years, I make a lot more than her, but as far as I'm concerned what's mine is hers. To be constantly bickering over who pays what after 9 years must be exhausting.