Living Single - Season 5 (1997)

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.

A strange client helps Max believe in her ability to practice law.

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. They 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.

Synclaire is furious to learn that her coworker has stolen her act and used it for his one-man show. She backs down when he tells her a sob story about needing money to pay child support, but she later finds out he has no children and he receives alimony. Synclaire gets a chance to audition for a role as a renegade nun for a new tv series. Max reveals that The insemination took and she is now pregnant. Khadijah agrees to support her even though she feels Max behaved impulsively.

Overton notices that Max picked her sperm donor from the same clinic where Kyle previously donated, following a near-death experience. When Max describes the donor, Khadijah and Synclaire believe it matches Kyle perfectly. Overton checks Kyle's records and confirms that Kyle is the donor that Max selected. Max decides she is not going to tell Kyle. The gang throws together an impromptu New Years gathering and invite Kyle, whose visiting his family in Cleveland for the holiday. Synclaire gets the role of the renegade nun but is upset that the job is in California and ...