Honestly one of the reasons I find it hard to approach him about all this is that I tend to be the type to hold it all in and then break down one day and list off everything upsetting me. When this happens, as it has a few times in the last year, he generally reacts strongly in remorse and just hates himself and cries and can't function very well for a few days after. I grew up in sort of a messed up household so I feel like I don't naturally have the right tools to communicate my feelings to him without just devolving into a rant or getting frustrated and walking out.

I do kind of resent his parents for that. Especially because I know that they know the situation, and occasionally his sisters and mom have pulled me aside just to ask if he's contributing and if we're happy, but I've never been one to trash talk a kid to his parents so I always say that things are going alright. But yeah, wealthy parents deciding that a kid isn't their problem just because he's been out of the house X months is NOT cool by me, and if I am ever in a position in the future to let them know that it really made our life stressful to have a source of funding they had promised him he would get taken away out of convenience, I'd really like to find a way to express that, or at least encourage my bf to. (They had told him before he left home that they would support him as long as he was a full time student making a good GPA, and actually pulled funding long before he dropped out. Part of the dropping out was the stress of needing to find a job because I was also running out of money at that time and we had rent to pay.) He's very intimidated by his parents and their successes though, as his dad is a respected surgeon, and his stepparents are a LEO and medical professional and they all expect very great things from him. His mom is a massage therapist and very reasonable, but considering that her home is actually owned by his wealthy grandparents and she has very few bills and is well supported by her family and her SO, she is very disconnected from the reality of a working life.