Ask the Little Bald Bastard

Dear Little Bald Bastard,
  I'm thinking about having your profile tattooed to my ass...which is your best side?
  What's better, dating someone below your potential so you get to walk around feeling superior but still have to wake up every morning next to them, or date far above your potential, get to wake up to THAT, but have to walk around feeling inadaquate?
- Love, Slight Taller Man with Hair
Dear Slightly,
  - My best side is generally whichever side you can't see. Although all you'd really have to do is have a pair of sunglasses drawn on your ass. I'm sure the resemblance to my face would be remarkable.
  - If you're going to do it, why not do it right? Who gives a shit if you feel inadequate? I feel inadequate enough when I look at myself, let alone at somebody else. If you can secure yourself the pleasure of going home to an attractive partner, go for it. Just be honest with yourself. If you're going to feel so outclassed that you're unable to keep from crying anytime someone flirts with your partner, forget it. Your self-doubt might lead you into the kind of jealousy that always seems to result in a restraining order.