Now to move on to the more personal issues - feeling comfortable with yourself. In this arena, I've spent most of my life feeling like I'm not good enough for anyone. That's what happens when you've been abused early on - you start struggling to please people but you feel like you always fall short. The first thing to realize is that other people's reactions to you do not indicate how good you really are. For one thing, we're the kind of people that can easily be manipulated and used. We want approval so badly that we'll do whatever a person wants us to do just to gain that. The people that use us will actually just be making us feel worse about ourselves and more dependant on other people's approval.
Take a step back and look at yourself, strengths first: you're a great listener (I know this from experience with you), you're dependable, you're fun to be with, people feel comfortable confiding in you (again, from experience, but also it sounds like Ashley recognizes this in you). This list is way too short, because I don't know more about you than I've seen in-game or heard from you in e-mail. There's a lot more that you're good at and that you've accomplished and achieved in your life. You probably down-play these things a lot (I know I did and still do). It isn't a sign or pride or self-centeredness to recognize your own strengths and accomplishments. You don't have to do this publicly. Just reflect on your life and notice the things that you've done right (even if the results weren't always good), the things that you've enjoyed, the areas where you've struggled to improve (the struggling is a sign of something good - you really want to do well or you wouldn't spend time struggling), etc.
The harder part is to stop depending on the feedback of other people to measure your own worthiness. People are fickle and people are needy. The more needy they are, the more they will abuse your need for positive feedback. But as you gain self-confidence, you'll find yourself attracted to friendships with different types of people - people that don't necessarily give feedback, or that will just be friends with you without needing things from you. Find people with similar interests and spend some time with them in those arenas. For instance, find some other gamers and spend some time gaming with them. Don't overdo it (especially at first), since it's easy to drive people away by trying to spend too much time with them. Just game with them for a few hours a week. Don't feel that you have to form a close bond or draw the gamers into other areas of interest. Just do the things with them that both of you enjoy doing. Eventually, friendship will begin to form that encompass more than one area, but don't rush it. Build friendships one step at a time.
Now for the weaknesses. These are the things you see most readily about yourself, and are tempted to see as your whole self. For example, being 10 pounds overweight. I've been 10 pounds overweight (if not more than that) all my life. Yeah, it means that I'm not the cheerleader that every guy wants to date. But I'm not horribly unhealthy. I just struggle more with physical fitness than those that have been gifted with athleticism and high metabolisms. This weakness is actually an opportunity for me to gain some strengths - I can set some small goals for myself, take some small steps and reach some small achievements. "Small" doesn't mean "not as good". It just means taking a little more time to do something and not trying to do more than I can handle. For example, I want to lose weight. I set a goal to attend an exercise class. Notice that I don't say I want to exercise a certain amount, lose a certain number of pounds or religiously attend that class for a certain amount of time. I don't really know what my abilities and limitations are yet. But just showing up at the class and putting in some effort to participate is a good start. If I go to the class and find that it's beyond my physical abilities, that doesn't mean that I've failed. I did what I set out to do by attending. I know now that that class isn't going to be the right one for me, so now I can try something different. It's not a failure - it's actually movement in the right direction, getting me closer to finding the things that will improve me rather than the things that will overwhelm me. In time, I'll be able to start setting those other goals (losing weight, exercising a certain amount, etc) as I learn my limitations and capabilities. This is true of all the "weaknesses" I see about myself. Weakness isn't a sign of failure. It's an area that hasn't had as much growth as other areas.
The hardest thing of all is to reverse the misconceptions you have about yourself that are based on the abuse you recieved as a child. I'll use my situation as an example again. My father was never physically abusive to me. He just wasn't a good father. He didn't ever give me signs of approval. He did, however, give me lots of signs of disapproval. He'd get irritated with me when I tried to get his attention or even when I was just doing the things kids do (like falling off my bike or getting burned or just playing house with my imaginary friends). All this negative feedback made me think that I was doing things wrong and that I had to be better at things in order to make him happy. I started trying to be really quiet when he was doing something so that I wouldn't distract him and get him irritated with me. I followed the letter of the law when it came to the rules he set. I worked to over-achieve in school. I did every last thing I could to get him to just smile at me. He never did, though. In fact, all my work really gained me was less attention. Even negative attention is attention - that's why a lot of kids mis-behave. Eventually, my father ran off with another woman and left me behind. He didn't even want me - he actually used me a leverage to get my mom to sign the divorce papers faster. Those early years formed my perception of myself for the next nearly-20 years of my life. I've pushed myself to over-achieve in as many areas as possible, running myself ragged, but never actually reaching a point where I was satisfied. Because I wasn't looking for my own satisfaction. I was looking for the satisfaction and approval of other people. And even when I got that approval, I distrusted them and imagined that they didn't really approve but were just saying they did to make me leave them alone for a while.
Since the time that I realized this behavior in myself, it's been a long, hard struggle to reverse the self-image. It's especially hard when a parent is the person behind the self-image. It's really hard to stop trying to appease your father or mother. The goal is to get a healthy and honest perception of yourself and to set healthy and reasonable standards for yourself. Getting an A in school was never good enough for me - I needed the teacher to see me as better than any other student in the class in order to even start to feel like I was doing things right. That's neither honest nor reasonable. You can't get a better grade than an A. Some people can't get better grades than a C when they're doing their best - that doesn't make them bad. It's unreasonable and unhealthy to expect more of yourself than you are actually capable of achieving.
Okay, so that's enough of my rambling for now. This is all stuff I've learned about myself, and maybe I'm just projecting it onto you because our cases sound similar, but hopefully some of it will be helpful. If not, just ignore it and move on. :)