(Cross post from vag chat) I'm pretty sure I know the answer i'm going to get allready, but here goes nothing. A little back story (Cliffs for the most part, whole thing is much more complicated): Spring term of my Sophomore year in college (2008) my mother was diagnosed with breast cancer. I had already been doing poorly in school, and ended up dropping an entire term and then out entirely. During this period I became semi-active in an online community, and I ended up meeting a few people. One guy and I hit it off, and we started talking. He was living in Colorado, and I was with my parents in Oregon. I can't remember exactly what lead to it, but I decided to move out of my parents place, leave my job at my father's company, and room with this guy in Colorado. Things went rather well, and my parents were surprisingly supportive. I drove out there in mid August of last year, with only a few thousand saved up. I was rather nervous, as this was the first time, ever, I had met someone via internet. I knew a bit about him at this point, and he with me, but there was still a lot that could of gone wrong. We had sex the first night I was there, it was my first time. I knew beforehand he was poly, and I didn't think it would bother me. It didn't at first, but gradually I got jealous whenever he payed attention to other people when we went out and did things. I really enjoyed most of the time I spent with him, but there were moments. A few months later we ran out of funds, and I had my parents bail us (me) out. I told him he could stay at my parents place, thinking that if I showed up with someone in tow the wouldn't say no. Boy was I wrong. It might of been the fact that my car broke down and it took us a week to get back, and three times as much money as I had originally asked for, but my father only let him stay in the house for a week. Then he was out, luckily he knew a couple of people in the area. I ended up working for my father again (have ever since), and he kinda dropped off the radar for a while. Whenever he did show back up I would make snide comments about his situation and relations, which was not the most mature thing ever... Somehow I ended up apologizing to him after I realized that the comments were hurting myself as well (I was depressed for weeks, thinking about him constantly). We started talking, and hanging out, in late January (2009). Since he was still unemployed, I started paying for us to go out. As a cliche, I asked him out on Valentines day. He told me that he didn't think it was a good point for us to start anything serious, and I had to agree. He ended up joining the Army reserves in March after still being unable to find anyplace that would hire. In April he was kicked out of the place he was staying after they got a paying roommate. Stayed with me for a couple of days, then ended up basically on the streets. Luckily he's met a few people who have taken him in since then, but he is still homeless and broke. My relationship with him has been very strained, and i'm feeling like shit because of it. He's adopted a "don't care" attitude with a lot of things now, and its started to get to me. I honestly have a problem with a lot of the things he does, like casual sex, tending to ignore me, ect. I've gone from being perfectly happy one moment, to pissed off and depressed then next. This past weekend we both said and did things that pissed the other person off, and i've been considering leaving him entirely now. I feel like i'm going to lose something either way though, and i'm torn at the moment. He ships off for basic in 7 weeks, and will be gone for six months. I'm trying to find a way to work through things until then, but everything I do only seems to push one of us further away. He's a really good friend, and almost the only one I have left, and I don't want to loose him. On the other hand, I can see how out relationship is unhealthy. I don't know what to do anymore. (If anyone wants clarification on things, feel free to ask.) What should I do/not do? Part of my problem is i'm still rather immature, i've been compared to a middle school aged girl before. His problem... is rather complex... Some added notes: 1. We are not dating. 2. I really do think he is a great guy.