I have a very good friend who I have known for about 15 years. We drifted apart a bit over the years with me being in the States (she lives in Germany), but we're still pretty close. She's in her 30s and has been complaining a bit lately that all guys she meets only see her as a friend and don't want to get romantically involved. She has been a single forever and I know she'd really like to have someone special in her life. Here's the deal: she is a very smart, funny, great person with a huge heart, but she's a total tomboy. And to be honest, not in the cute way. She has had the same unflattering haircut since I've known her (she's had it all her life). She grew up in the country with brothers and I think her parents simply always sent her out to play with the boys, get a haircut at the same place, etc. Now, I like her just the way she is, but I have been contemplating telling her the truth about her looks. It's not that she is ugly, at all, she would be adorable with a different, longer cut and some style. I am only thinking about intervening like this because she has expressed unhappiness about her situation. I wouldn't want her to change for anybody, but, at the same time, I feel like someone should tell her that she looks like a 16 year old boy (not that harsh, of course). Am I completely out of line? Should I just stay quiet? I know that looks aren't everything, but at the same time, they are important.