My girlfriend and I have been together five months. She's wonderful and beautiful. She lost a lot of weight before we met but still doesn't have a very good self-image and calls herself a "fat chick" all the time. She wears a lot of makeup, which I don't care for. I try to emphasize how beautiful she is and that she doesn't need so much makeup. She dismisses me and says people will be staring at some barely noticeable blemish or something.
I find her so much sexier without the makeup and I want her to feel good enough about herself not to need to cover up. Should I let it go? Do I have any right to ask her to do things differently because I find it more attractive?
Answer: By tiptoeing into the makeup issue with your girlfriend, getting deflected, and factoring in evidence of her shaky self-image, you've demonstrated that you: know she's fragile; are wary of controlling; aren't one of the disarming, charismatic few who can say, "Ugh, take that spackle off, you're way too pretty for that" - and get away with it; and not in the kind of solid, trusting relationship that allows the less charming among us to speak so freely. Your relationship may get there, but it's not there now.
And you won't get there if you treat the makeup as a surface issue. It runs as deep as her insecurities, which you can't help her with unless she lets you. For that you need patience, sympathy, acceptance (makeup and all) and time.
What you're essentially asking is whether your girlfriend will ever accept and trust herself enough to accept and trust what you give her, be it a genuine compliment, constructive criticism, or love. It's a question I can answer only with another question: Are you dedicated, eyes open, to sticking around to find out?