I'm nearly 40, and I've spent years trying to improve my appearance and confidence. Unfortunately, neither has translated into much success with women. I'm very unhappy with how I look, and while I've made improvements through fitness and other changes, I am not physically attractive.

Financially, I'm doing alright. Decent job, retirement savings, car, comfortable apartment. Now I've got approximately $100K to spend, and I'm seriously torn between two options.

Option one: Buy a house. Build equity, gain financial security, and make the sensible adult decision. It wouldn't be my dream house, but it'd be something to call my own.

Option two: Improve my appearance. Extensive facial cosmetic surgery and limb lengthening from 5'9" to 6'0". The hope is that becoming more conventionally attractive might finally improve my dating and sexual opportunities, along with my confidence.

I know surgery won't magically make me confident or desirable. I also understand the serious medical risks. But I don't think confidence and appearance are completely unrelated either. Feeling physically desirable, and actually experiencing that desire from other people, might make a meaningful difference in my life.

I'm not looking for just one relationship. I'd like to experience casual dating, sex, and different relationships while I'm still young enough to enjoy them.

So here's my question: Can improving your appearance be a worthwhile investment in your confidence and happiness, even if it means sacrificing a significant amount of financial security?

Today I was waiting for the elevator at work with my work crush. He made a comment that I always look like s*** at work, and have sad/crying looking eyes. I told him it’s just my eye shape. I know I am overly sensitive about things and I’m pretty sure he isn’t calling my features ugly just the condition I’m in. Like if I had bad skin, messy hair, sweating, sick, etc. He isn’t lying but I keep rethinking the moment and it lowered my self esteem. And to think I thought there’s a chance he liked me since it’s always awkward between us. What do you guys think I should do?