ESH or NTA (not sure) Okay, what the hell is this relationship? If someone’s getting money from their parents… let them do that.

I’m not sure why you’d insert yourself as someone to give them money all the time. If you’re well off and feel comfortable paying for dates or a higher portion of rent, that’s one thing. But, offering to pay for portions of his schooling and everything in-between opens your relationship up to a lot of tension (like this).

He’s pretty dependent on his parents, and it sounds like he’s not too money-wise yet. He’s handling this poorly because of it. I’m not saying that’s an excuse. But, it just seems like he has a juvenile perspective on money, so don’t be surprised when he acts juvenile with money situations.

I feel like you should just let him continue to get support from his parents, graduate, get a job, and learn what it’s like to support himself. That way he’ll have context for what it means to make commitments involving money.

Instead, you’re playing this weird intermediate financial support system. Like I said earlier, that just sounds like it’s opening up your relationship for tension.