After Overton's van breaks down, he buys a Lincoln from a police auction. Synclaire makes him get rid of it when Max tells them it once belonged to the mob. Regine invites her mother to dinner on a lonely Saturday. Her mother meets a rich man and dates him, but Regine feels he will dump her soon.
Kyle lands Synclaire a role as a clown sidekick on a popular kid's show. The star of the show is a 12-year-old tyrant who is rude so Synclaire tries to teach him respect. Overton still has not overcome his clown phobia. Khadijah accuses Regine of stealing her grandma's cookie recipe to win a baking contest.
Max and Kyle lie to their friends about out of town trips in order to sneak off to a hotel together. Regine is suspicious of them and is determined to find out if they are together. While Kyle is away, Synclaire and Overton cohabitate in their apartment to see what it would be like to be married.
The girls realize that their busy schedules are causing them to miss out on imports events in each other's lives so they plan a girls' night out. Kyle invites his boss to a fight party and Overton gets upset when Kyle's boss doesn't pay like everyone else.
Overton moonlights as a handyman in Max's building and gets her evicted when he accidentally reveals her illegal satellite hookup to her landlord. Khadijah, Synclaire, and Regine hire a housekeeper because they are too busy to keep it clean.
Max asks Khadijah to help her uncover an embezzlement scheme in City Hall. Khadijah's new reporter at Flavor has unconventional ways of getting information for his stories. Synclaire tries to help Overton cope with the Cleveland Browns move to Baltimore.
Kyle believes his brother, Damon, is throwing away his life by not having a steady job and sets his brother up for an interview with his firm. Damon thinks Kyle works too much and is not really enjoying life. When Regine refuses to plan Synclaire's bachelorette party, Max and Khadijah get Regine's high school rival, Ava, to organize it.
Kyle buys a one way ticket to London for Max in hopes that she will move there with him. A friend of Russell's, Tripp, moves in and takes Synclaire's room. Overton and Synclaire sail off on their honeymoon, but it is disrupted by a pushy activities director. The newlyweds finally get away from her only to find they are stranded on a deserted island.
Khadijah goes on a date with Cedric Ceballos of the Phoenix Suns. She gets so nervous before the date that she gets a headache, Max gives her four of what she believes ito be Aspirin, but it turns out to be tranquilizers. An older gentleman comes to Synclaire and Overton's new apartment, looking for the previous tenant, but they cannot bring themselves to tell him that she passed away.
Synclaire spends most of her evenings at rehearsal and leaves Overton feeling neglected. He goes out gambling with Tripp and Russell and end up gambling away money he and Synclaire set aside for a new bed. Regine's new relationship is complicated by her boyfriend's relationship with his dog.
Max's former law school professor and mentor, Clayton Simmons, comes to town for a lecture. Max has always had a crush on him and plans to make a move. Khadijah confesses to Synclaire that she once spent the night with Clayton and can't bring herself to tell Max. Regine throws out Tripp's date after she wears Regine's robe and uses her bubble bath. Tripp gets back at Regine by not showering and purposely stinking up her party after she cut his soap-on-a-rope.
Synclaire and Overton bring home a pile of classic records from the '60s and it gets the gang singing and dancing. Khadijah tries to get some work done and is annoyed by the loud music so she goes to the hallway, but she ends up falling asleep and dreaming she is in an old school singing group called the Flavorettes.
Regine interviews to be an event coordinator for a charity event. She tries to impress a handsome entrepreneur, Dexter Knight, by saying she will take 10% off the lowest bid. She quickly realizes the budget is much less than she hoped and must cut corners. Max has not given Overton and Synclaire a wedding gift so she gives them a blank check, they have a hard time coming up with an amount.
While traveling to a football game, Overton, Tripp, and Russell pick up a hitchhiker. She turns out to be wanted for robbery. Dexter asks Regine to move in with him and she accepts, but needs help from Khadijah on how to break it to her mom.
Synclaire auditions for a play only to realize all the female roles are taken. She dresses like a man and assumes the identity of James "Jimmy" Overton and wins over the directors. Overton is distressed by the fact that Synclaire has to keep up the appearance of Jimmy and he can't be affectionate towards her in public. Khadijah helps Tripp with a jingle and thinks she has what it takes to be a jingle writer.
Khadijah keeps dreaming of kissing Scooter in a hot tub. Max drags Khadijah to a new age retreat where she hopes to find her purpose and Synclaire tags along. Khadijah is shocked to find Scooter and the same hot tub from her dream at the retreat. The two discuss their relationship and work and decide to give it another try. Through hypnosis at the retreat, Max discovers she was a man in all of her previous lives. She realizes she must do something she could not do as a man; have a baby.