From what you wrote about wanting to be a winner, I take it you consider yourself to have been a loser. I would do some serious thinking about whether life is about winning or losing because it implies that when you win, someone else loses. It's a scarcity mentality. There is plenty of money, love, and influence to go around for everyone to share.
I would think more in terms of being real, loving, and having integrity, than in terms of "winning". I would think more in terms of being positive, fun, humble, secure and mature which will attract those kinds of people (including women) to you. You do not want to attract merely "winners" -- unless you define "winners" as people with integrity, courage, love, maturity, humility, and other such virtues, independent of how much the markeplace values their skills and qualities. Most people define "winners", though, as people who are popular and highly regarded, powerful, and/or wealthy. That's not the way forward. Not that there is anything wrong with popularity, power or wealth -- it's just that they are secondary concerns. What you want is a fulfilling and joyful life. Simply possessing things doesn't produce that.
I commend you for taking stock of your life and taking positive action to make good changes. You will have a set back now and then, don't flog yourself about gaining back some weight, just do what you're doing -- get back to the gym and keep going. But at the same time, do think deeply about what your values are, what you really care about, and the sort of people and causes you really want to devote yourself to. Don't be in a big hurry to adorn yourself with a woman to prove you're "not a loser". Relationships can be wonderful or they can be toxic ... you're still figuring out who you are and which way is up, so don't be in a hurry for serious relationships with specific people. Keep it light, meet a variety of women, learn the ropes. The median age for marriage is getting quite high -- it's about 27 years old in the US -- there is no hurry.
Hang in there, and good luck.
Last edited by SonoranBob; 02-28-2008 at 02:01 AM.