It would be creepier if Howard was so out of touch with pop culture that he didn't know half the women on the brackets.
Gary: Stacy Keibler or Kate Beckensale?
Howard: Who is Kate Beckensale?
Gary: Kate Upton or Meghan Fox?
Howard: What was Kate Upton in?
Gary: Miranda Kerr or Kaley Cuoco?
Howard: I don't know either one.
I would be more creeped out if I wasn't so embarrassed that I used to think Howard was on the cutting edge of pop culture. In fairness to Howard, Kerr is married to Orlando Bloom and he is too big to ever appear on the show.