First off, it is MEN who judge other men by the amount of women they have dated. Women don't do this.
I think it isn't a matter of your looks but rather your defeatist attitude. Put on a happy face and have some self-confidence. You will draw women like a magnet.
Money is not everything. Yes you can make a lot of money as a chef in a fancy hotel, restaurant, or resort. But it's very competitive, and sometimes your advancement is not based exclusively on your ability as a chef. And do you know how many hours a day those guys work? It's a very tough...