<human>: Provide a brief overview of the text.

My romantic life is a mess, and I willing to admit that I am the problem.  I don't want to turn into some arrogant jerk or a PUA, but I realize that I am too much of a Nice Guy and a pushover.  I know confidence plays a big role in how men are perceived by women, but I am always am afraid of coming off as some sex crazed douche.  

I want to stay true to myself, I want to just learn how to put myself of there more and be ok with rejection.  I am not trying to take every girl I can back to my place, it's just not who I am.

Some background on me:

I was always overweight, and peaked at over 400 lbs.  I am down to 255, and still have a ways to go.  This is always what was in my way when I met new women, and killed any confidence of flirting or asking them out.  Sometime some would become my friends and over time, we would be really close friends, usually inseparable.  Sometimes we would be mistaken as a couple, but it always stayed platonic. I don't fault them, I lacked the confidence to ask them out and I know I am not an attractive man.  Whenever I found myself in these friendships I would become numb to other women, because emotionally, I had a friend with benefits.  Eventually I become too emotionally involved and it leads to hurt for both me and my friend.

I now realize this is not healthy, and want to live a normal dating life. Not so much casual dating, I understand that might be necessary to eventually meet someone, but I would like to have a semi-long term relationship with someone who is mutually there for me.
<bot>: How do I become more confident, without becoming a jerk?  How do I get to know someone, when afraid of an immediate rejection, or having it just turn into a friendship.