After performing stand up about being newly single, Sherri (Sherri Shepherd) accepts an offer from Doug (Chris Williams), an old friend who has had a crush on her for years. Sherri finds herself in a predicament about telling Dr. Gregg about her date with Doug, but she ultimately admits to him that she'd like to date other people. Things take a turn for the worse, however, when Doug reveals he's not over his last relationship and has a complete emotional breakdown. Meanwhile, in order to get some old timecards signed, Donna (Cindy Caponera) seeks something in return from Angie and Summer.