You are talking about a man you know in real life, yes? And he has not asked you out? I think you should keep working out because you enjoy it; lose weight because you want to, and keep your eyes open for a man who likes you as you are right now. There is no need for you to be apologetic for your looks, and I don't think it is a healthy relationship if a woman has to beg a man into loving her 'in spite of' her flaws. Too many men will use that insecurity as a weapon to control the relationship unfairly. And that's not love. And what I have written here applies to men, too: I don't think it is a healthy relationship if a man has to beg a woman into loving him 'in spite of' his flaws. And come to think of it, it applies to same-sex relationships, too, imo. You're special and unique and beautiful when you are the best you as you are right now. Live your life now.