Hey TE,
I can speak from experience that if your weight issue has affected your self-esteem, which it has, then it is most definately affecting your desire to date. When you are not comfortable with yourself, whom you know the best, you are never going to be comfortable with anyone else. It is just pure human nature. I can tell you this that since I have gotten in better shape and actually attained the body that I have right now, I have more self confidence, my relationship with my wife has gotten better, I am not ashamed of my appearance (especially with a shirt off now) and it flow over into everything I do. Never in a million years would I have posted messages on a forum, let alone give advice.
Make sure you are ready on the inside before you begin your change on the outside. It sounds like you have the right motives and desire to get in better shape. Now just get moving. There are no magic pills or diets. Just hard work. There is hope and it really does not take that long once you put your mind to it. I am living proof and I know a lot of other people that have done the same thing. I can share what worked for me if you would like. Let me know.
Robert
MDB HarleyGuy