BF going back to school while I work..am I being selfish or do I have the...

...right to be feeling upset? I appreciate anyone taking the time to read this! Ok so here's the deal. My boyfriend and I have been together for about 2 1/2 years. I feel I have always supported him in different ways. I lived alone with my daughter and he wanted to move closer to have a shorter commute to work. So he moved into an empty room at my mother's house to pay less rent, be closer to me and work and also pay off some CC debt. Most of the time he would be at my house and he'd be at my mom's twice a week which where the days he'd be with his son. He would only give me $100 and buy groceries even though my rent was $900. At that time I figured it was fine even though he was always there with me because he was helping my mom with $400 for the room at her place. Eventually he got tired of not having a real "home" so to speak so I agreed to move into a new apartment with him and live together. This all happened over the course of maybe a year or so.

We lived together for about 5 months and split the bills half way down. He had always made double my salary but I still didn't have a problem with it because I could afford it and I would be paying less by moving in together. Prior to the move-in I had discussed going back to school and finishing so I could make better income. He always said he would support me with it but at the end I was fearful because I didn't wan to entirely depend on him in case he split or it didn't work out. Also when I would try to talk about school with him he'd avoid the conversation or not really seem interested. I had a fairly good job and didn't want to lose that if it didn't work out. Fast forward.

We are living in this apartment together for about 5 months and it gets real rough between us. Constant arguments, it got bad. He moved out and we broke up, I guess we weren't ready to move in together full time. After the break up we decided to make it work and went to counseling. In about less than 2 months of him being at his own place he lost his job. I wound up finding him a job at my workplace - We didn't exactly work together though. Im an independent contractor and he was on site. My boss allowed him to live rent free at a guest home to avoid a very long commute to this workplace. He would then come to my place on the weekends. He didn't last and quit a little over a month later because he wasn't happy and disliked being in another town during the week. He quit before finding a new job. He came back to my place and now he's not looking for a job but is trying to get back on unemployment and wants to go to school. I feel used and abused at this point. He says it's to help both of us but it doesn't feel this way to me.

Am I being selfish or should I be supportive and not be upset about his decision? Also when he was at the job I hooked him up with he said he couldn't afford to give me half the rent so he was only giving me $300 because the new job paid less- Rent is $1400. Before he moved back in I demanded he give me $700 which he has done. I told him if he gets unemployment and goes to school he will have to continue to give me $700. He agreed to this. Im also having doubts because receiving unemployment for him was $600 less than what he was earning at my job. If he has agreed to pay the $700 now why did he say he could afford it while he was working. This guy says he loves me and wants a future with me. He says he wants to marry me and all that. He asks if I trust him but honestly I don't. I just always feel short-changed. Should I be happy that he's going back to school? Or resentful because he always said he would support me if I went back but that didn't happen? Im confused.
 
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