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I will be honest that I am insecure, sensitive and sometimes get jealous. I guess those are my flaws that pushed him away?
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Everyone has flaws. Is it really true that if only you were perfect everything would be fine and therefore things are all your fault? I suspect that he has flaws as well.
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I still carry guilt and regret with me. A lot of my guilt comes from wanting to pursue a teaching job abroad. I want to work in adult education/ESL programs for a career and thought that we could make it work long distance. He supported my decision but I still think that he broke up with me because I wanted to go. It makes it seem like I didn't care about us but I wanted to make it work no matter what.
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It equally can be argued that he didn't care about "us" in that he gave you a mixed message and in the end broke up with you because you wanted to develop a self as well as a relationship.
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After we broke up, we stayed 'friends' but I knew that was a bad move because I still had feelings for him.
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I agree with you on this.
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We hooked up a lot and I lost my self-respect (hooking up is something out of character for me since he was my first. A few months before we stopped talking, I avoided him and declined when he wanted to meet up. My gut was telling me that he was seeing someone else too. He still wanted to be my friend and told me he cared a lot about me.
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Caring about you, in my perspective, would have been better shown by not hooking up with you under the circumstances. You were wise to stop seeing him.
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But I just couldn't be friends then and still feel regretful and wonder if I made the right choice. We haven't talked to each other since last summer.
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I think you made the right choice. It was too much to tantalize you with the closeness of hooking up while at the same time pushing you away in a relationship sense. It was too much to ask you to endure.
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I get jealous of him easily and I think it's because he's had a lot of success while I am still figuring things out. He bought a house and a car last year and now he has a new girlfriend. His life is wonderful. I'm still working on my career and me - that's pretty much it.
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I wonder why he in particular gives rise to these feelings of jealousy. There are lots of highly successful people in the world, do those people (e.g. celebrities, athletes, executives, politicians etc.) make you feel jealous as well? It might be worth looking at the jealousy of him in particular and seeing what you can make of it.