Steve manages an all-girl singing group called Jail-Bait, and books a gig for them that he hopes will revive his own show-business career.
As Steve is about to celebrate his fortieth birthday, he makes his students list their life goals. Steve finds a similar list he prepared 20 years earlier, only to discover he has achieved little of what he wanted. Meanwhile, as Steve learns Regina is dating multi-millionaire basketball star Jordan Maddux, a pregnancy test indicates Lovita and Cedric are going to have a baby.
Regina recruits Steve and Cedric to perform at a charity function to impress the snooty wives of her boyfriend's teammates, since she's having some trouble fitting in. Bullethead and Romeo join Lydia's new club, but their ideas on how to spend the organization's funds cause division among the group's members.
Steve, depressed and feeling jilted over Regina's impending nuptials, kicks his effort to get her back into high gear when he hears of their accelerated plans to elope. Meanwhile, Lovita tells Cedric to flirt with the female landlord of an apartment they want. Lydia discovers that she was adopted.