Trying out a new shapelier bra Whitney gets more than she bargains for when she entices Alex with her enhanced look. After Roxanne calls it quits with Lance, she asks Mark to help pack up his stuff, but things become complicated when Mark decides to take advantage of the situation. Meanwhile, Lily and Neal begin discussing a pre-nup, but the conversation leaves them wondering if they should even get married.

When Whitney finds a box of stuff from Alex's old girlfriend in the basement, she confronts Alex about it. Not satisfied with his answers she turns to Mark and gets more information than she bargained for. Meanwhile, trying to be the perfect roommate for Roxanne, Lily only seems to make things worse. Later, Neal enlists Whitney's help to stage a post break-up run in with Lily hoping to make things less awkward.