Max and Khadijah grow weary of Regine's spineless boyfriend, John, so they joke about sending him a letter from Regine asking him to set her free. Max follows through with the plan, and Regine is devastated when John breaks up with her. Max and Khadijah go to John's house to explain the joke and ask him to take Regine back. They also suggest that he stand up for himself occasionally, rather than letting Regine walk all over him. Before John can come to the apartment to make up with Regine, she brings home her new boyfriend Keith, an artist who was painting a mural at the television studio. John arrives with flowers to tell Regine that their relationship is over, and begins pursuing Max. (He believes she sent the letter because she wanted him for herself.) Kyle's new girlfriend, Kimberly, begins coming on to Overton every time they are left alone together. Kyle refuses to believe this, but Kimberly freely admits to it when he confronts her on the roof. Kyle orders her to leave, and a be

Kyle receives a promotion, but becomes extremely disenchanted after realizing that he is no longer allowed any contact with clients; the entire job consists of attending meeting after meeting. When Kyle is asked to speak before a church youth group, a young man who has followed his career closely suggests that he use his creativity to make his job more interesting. Kyle proposes an intermediary position, in which he would be involved in middle management, yet still work with clients. He must take a pay cut, but feels it is worth it. Meanwhile, Max tests Regine's claim that she doesn't mind when Keith paints portraits of nude models by volunteering to pose. Regine finally admits her jealousy, and Keith agrees to work with her to put her mind at ease.

Tag: Rev. Taylor tries to sneak out of Overton's lecture while kids sleep.

Laverne is very impressed with Keith at their first meeting, but things take a turn for the worse when Ms. Hunter catches Keith and Regine in a romantic interlude on the roof a few days later. (Max, who observed the entire encounter from her apartment, documents it for the neighborhood newsletter.) Regine cannot get her mother to speak to her, so she comes down to her favorite bingo parlor with Khadijah to confront her. Laverne explains that Regine's behavior reminds her of the time that Regine was conceived in the bleachers during a Mets game. Regine assures her that she has control of her life, and there is no reason to worry. When one of Laverne's bingo cards is a winner, she and her daughter celebrate with a shopping spree. Overton decides to pop the question to Synclaire. He spots the perfect ring, but must negotiate with the eccentric old man who presently owns it.

Tag: Overton and Ray take a ""chopper"" ride.

Regine is outraged when Keith ignores her at his opening (aside from asking her to change a light bulb in the bathroom). He refuses to defend her when an art critic comes on to her. Russell tells the man to take a hike. After her friends point out that Keith has always seemed aloof, Regine goes to his loft to confront him. She threatens to break up with him unless he begins to take their relationship seriously, but Keith says that he cannot change. Regine comes by the Flavor offices to meet Khadijah for lunch, but she has to cancel. Russell agrees to give Regine a ride into town, then forces her to stop at his aunt's house for lunch. She cheers up after eating a delicious meal and dancing to lively reggae music. Regine begins consulting self-help books for tips on how to land the right man, but finds herself thinking about Russell more than she would like to admit. Kyle and Max go to war over the right to park in a spot in front of the building. When they get into a collision, they bot