Relationship encouragement (not as bad as it sounds)?

Few points about myself, im a second year college student in the IT field and I play a hefty amount of video games. The reason im on here today is because I have issues with starting a relationship. And when I say relationship I mean a dating relationship. I've had a couple of girlfriends and the start to the relationship was being at the right place at the right time and literally nothing else. I was the "rebound relationship" if you may. One ended because I was cheated on and the other was over losing my OWN $20 bill. These ends have led me to the idea of "rebound relationship" because they both seemed to want to move on. It isn't like I have bad relationship skills either. In fact, I've set up more people and saved many relationships than I can care to remember. (One of the saved relationships are due to get married!) I guess the root of my issue is self esteem. My self esteem is somewhere between non existant and just above non existant. Which may also lead to my video game habits (you know, the whole "winning makes someone feel better about themselves" thing). But I just can't seem to get a relationship. I don't have any girls im eying up at the moment either. I have been shot down by far too many people in high school, thus leading to further self esteem issues. Now I know everyone has their "type" that they are looking for (I know cause I have a few I wont date, but EVERYONE does) but it seems like I fall out of everyones "type." I am slightly over weight (210) and am working on (quite effectively actually!) On some acne issues. That all said and done, im looking for advice on ANYTHING to improve my situation and I can't really accept answers like "just do it" cause that really doesn't help.