When Tom is unaffected by low scores on a career aptitude test, Allison decides that Gary needs to set a better example for their son. Gary calls an old buddy who works at a radio station, and ends up getting offered a job - an offer that Gary misinterprets.
After Allison's new boyfriend offers to take Louis to New York for his birthday, Gary tries to outdo him but shouting out a promise he could never keep.
Desperate to get the job as a radio sportscaster, Gary attempts to convice Sasha into listening to his demo tape, while Louise comes up with a way to protect Tom from the school bully.
Gary is determined to prove that he can handle a one-night stand without getting attached.
When the radio station's normal sports announcer gets arrested, Sasha agrees to let Gary take over, giving Gary his first big break. Meanwhile, it's her school's volunteer week, and Louise participates by making a video consisting of well-wishes for Uncle Mitch and the rest of his team in the Marine Corp.
Gary finds out that dealing with two careers and two kids is harder to do than he thought it would be.
After her new friend Sophia prefers Gary's company over hers, Allison feels jilted.
After making a disastrous attempt to prepare a Thanksgiving feast for Sasha, Curtis, Jack and the kids, Gary turns to Allison for help.
Gary tries to keep the secret of letting Louise attend a popular girls party from Allison, while Sasha contemplates having more than a working relationship with Gary.
Gary and Sasha's first date is interrupted by Allison, so Sasha starts to really notice the bad sides of dating a divorced man.
Gary and Allison take it upon themselves to probe into Tom's personal life when they think he is hanging out with the wrong crowd at school, while Sasha does her best to flirt with a professional surfer named Laird Hamilton.
Worrying that Tom may be hanging out with the wrong guys at school, Gary and Allison take it upon themselves to probe into Tom's personal life. Meanwhile, Sasha flirts with professional surfer Laird Hamilton.
Because his relationship with Sasha has gone to the next level, Gary must now decide if he should put his career on the line to date his boss or if it's not worth it. Meanwhile, Allison tries to teach Tom a lesson in responsibility.
After Sasha gives Gary an awesome Valentine's Day gift, he tries to outdo her by giving her the perfect gift. Meanwhile, Allison tries to bond with Tom and Louise.
In order to get Tom on the wrestling team after the original plan backfires, Gary challenges the coach of the team, a former high school nemesis, to a wrestling rematch.
Gary helps out Mitch to figure out what he'll do for a living when Mith returns from overseas. Meanwhile, Allison is hired as Curtis' and Charleen's wedding planner.
When Gary finds out that he and Allison's divorce papers were never filed, he uses the information to manipulate her into giving him his stuff back. Meanwhile, Allison's sister Rachael comes to town and gives Mitch a makeover.