My roommate is a beautiful soul. Her wardrobe, not so much. She wears cheap, often tacky dresses (most of them with a “geeky” theme like Star Wars, Dr. Who, etc) all the time. Many of them are full-length ball gowns with petticoats underneath. Her employers appreciate her hard work and dedication, but I’ve noticed they never take her very seriously and she’s never been put in charge of the department she was trained to take over. I adore her geekiness and think style is personal and subjective, but I know not everyone else sees it that way. Her last boyfriend ended things after she wore an R2-D2 gown to his sister’s black-tie wedding, even after he begged to buy her a new dress. She rarely gets a second date. I have tried getting her to try on other clothes, but she seems uninterested. I think it’s entirely possible the outfits are a shield for her insecurity. I believe there is someone out there who will love her the way she is, but part of me wonders whether it’s time to sit her down and be honest because it’s holding her back professionally and romantically and she doesn’t seem to understand why. I’m worried I’ll lose my friend. Should I butt out or speak up?