Hello, I'm going to get straight to it. I went out with someone last year and everything was amazing. There were a few things that seemed odd but they were mostly money/credit related and I don't care about that too much, I make my own money.
Anyway, 3 or 4 months into dating we have the talk about getting more serious and moving into committed territory. This is around June or July. I had planned a trip to Hawaii by myself for my birthday, to which he invited himself along and I allowed him to do that though I wanted to have some time to myself I felt bad telling him he couldn't stay the whole time.
From the minute we got there he seemed really stressed, he had just been fired from a job he only had for a few months. He picked a fight with me over every little thing and I come from an abusive home and have learned to stand up for myself so I wasn't having it, he threatened to leave a few times and went out of the hotel room to the elevator. He didn't leave, I laughed because he didn't have a phone or money. The phone he had was part of his job so we he went phone less. So he's being up and down the whole trip and on my birthday he's not very nice or sweet at all, picked a fight with me over dinner. The next day I said we needed to talk and I said to him he needed to make up his mind if he wanted to be together or not and then stick with it because I don't need this **** in my life. he cries, tells me he loves me and wants to try. I think great, we get back home and he suggests we apply for an apartment together. After we filled out the application and didn't get it, he's still without a job, he suddenly tells me he doesn't know if he's gay or straight or whatever. So I say what?! ok, I take him seriously, he has some issues as I could see, so I offer to buy him a ticket back home so he can come out to everybody and start over. UHH ok. you still with me?

He doesn't ever leave, I catch him telling his roommate that he "broke up" with me and that he still liked me but that things just didn't work out. The next 3 months he won't talk to me, ignores my calls, I got him a phone in my name when we were good, and he won't pay me for it. he's not working, i write him just asking him to pay me and return my items from his home and that would be it. Somehow in January he ends up falling out of grace with his roommate, he lets me talk to him about some of his past and his current issues around money and depression and we slowly begin talking frequently, I didn't expect much. He jumps right back in, says he's always loved me that he really wants to try and so on, he's getting ready to move in with me and then in april he tells me he can't even be friends, pretty much over night. We had some arguments sure, but I feel so stupid, I fell for this **** again. He owes me about 2k and has some items of mine at his house which he refuses to return. Thing is we live in the same neighborhood, I see him all the time and he ducks me. Writes me nasty emails about how I'm the reason his life was bad, he never loved me etc etc, he shaved his head into a mohawk and got a tattoo, never gave me a nickel on my loans. He got a job in March, with a resume I wrote for him, he is still working there thank god. he doesn't have any family in town and his friends are just people he has drinks with, or whatever. not real friendships, he can't stand getting close to people.

I'm getting ready to file a small claims court case for the money tomorrow and I have written the relationship off, I've told him I think that he is ill. His father had a long stint with heavy drug addiction and homelessness, they are both great illustrators, amazing artists. I'm still sad but I have to move on with my life and he has never been really great to me anyway. I should mention this story, the night before we went to hawaii i had a small pre birthday gathering for myself with some friends, nothing big, just six or seven people hanging out talking and he seemed to have an ok time there but when we got home he said to me "none of your friends really liked you because of the way you talked over everyone" I had no idea what he was talking about, I'm a great listener so I wrote it off as him being jealous or whatever because I was the center of attention for a minute or two. He also binge eats on nasty foods, it's insane to watch him eat huge amounts of garbage. he has admitted to me once that he was suicidal in december. it took him 6 months to apply for a job after we got home from hawaii and he had no explanation for that. His unemployment led me to loan him money for rent and whatnot, he's very charming and his roommate let him live rent free for some of the months during which we weren't talking.

So my question is this, how consistent is this with bipolar? and also, I have access to the contact information for his sister and father and I would like to tell them about my suspicion but i want to make sure that this isn't weird or overstepping my boundaries. as i'm sure that he would hate to find out i did that and immediately negate it by calling me a crazy *****. Thank you to everyone who took the time reading this rant and I hope you have some thoughts to share with me.