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this post was submitted on 25 Jun 2026
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How long have you known him? If you two have only just met or met very recently then it's very weird behaviour for sure. Heck it's a little weird him being this forward so soon, if you did know each other only as friends before this.
The Backrooms outing was actually the first time we met. To be fair, I did pull my friend’s boyfriend aside and ask him about it, and he said I had no reason to feel uncomfortable because his family has money and apparently he’s just a very generous person by nature.
It's quite possible that he is indeed a generous person, but still be careful. Truly generous people like that are very far and few in between, at least in my own experience, so most are usually that nice early on when they want something from you. Not trying to put him down, because we don't know him... But be careful.
Major red flag then - if he's not even spending money on you he earned himself, then he's just seeing if he can buy affection. He sees this as a transactional situation, and he will get nasty the moment he feels he won't get the returns on his "investment".
Btw. as others have pointed out, I also agree that it is already a red flag even if it's his own money (paying for time/activities spent together on a first date gets a pass from me, but paying for things you buy for yourself does not). And the comment about the transactional nature also applies there.
Way to tell if someone cares about you: they ask meaningful questions about you, your life, your thoughts, your personality. Red flags: they focus on doing things that you pay for, and they mostly talk about themselves or job/money.
I mean that's possible... But no, it's not certain at all.
My girlfriend has rich parents, she's the type to do this kind of stuff, and we've been together for 5 years. She's also a communist and a class traitor. She sees generosity as fairness: if her family has a lot and her friends have little, she's got more of a responsibility to provide for all of us than we do. Also, she's never worked a paying job in her life and has no clue about the actual value of money. She's willing to give away money because it's just not that valuable to her.