Dave's fling begins turning into a relationship he doesn't want; Jane tries to help Alex find a roommate.

Max agrees to dress up as Santa for Penny's charity event. Jane accidently gives housekeeper Gita the envelope stuffed with money for their big Xmas getaway to Turks & Caicos, instead of the $200 Christmas tip she had planned. Dave cashes in all the homemade coupons Alex gave him as gifts from past Christmases.

Dave has a surprising reaction when his shrink starts dating Penny. Max and Jane's fight over a sweater leads to a strange competition, and Alex and Brad bond when they discover a shared interest.