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.

Gary is determined to prove that he can handle a one-night stand without getting attached.

Trying to juggle two kids and two careers, Gary overextends himself.

To prove that men are not only interested in only beautiful women, Gary dates Louise's favorite, but plain school teacher.

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.

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 discovers that he and Allison's divorce papers were never filed, and he uses this information as a way to reclaim some of the things Allison kept. Allison's sister Rachael gives Mitch a makeover while she is in town visiting.

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.

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.

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.

When Mitch returns home from overseas, Gary tries to help him figure out what he'll do for a living. Meanwhile, Curtis and Charleen hire Allison as their wedding planner.

After her new "friend" Sophia prefers Gary's company over hers, Allison feels jilted.

Gary buys a boat to help Tom impress a girl, but his scheme does not go as planned; Gary must turn to Allison's boyfriend for help.

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.

Gary and Sasha's first date is interrupted by Allison, so Sasha starts to really notice the bad sides of dating a divorced man.

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.

Gary turns to wrestling in order to settle a fued between him and the wrestling coach, after he fails to help Tom make the team.

Gary must deal with the news that his ex-wife is engaged to another man all while trying to balance single fatherhood and a new relationship of his own.

Gary and Allison decide they need to make some new boundaries and distance themselves from each other after he undressing in front of her.

Gary realizes that if he can stop paying spousal support, he can buy Tom lots of toys. He sets about trying to encourage Dr. Krandall to set a date.

Gary makes a threat to show Allison's racy photographs he received from her on their first anniversary to everyone, when she refuses to give back his pool table he bought for her as a gift.

Gary is afraid that Vanessa and Allison's blooming friendship will mean doom for his relationship with Vanessa once Allison sets up a gloomy impression of him. Gary wishes all the former women in his life will make friendships elsewhere.

Gary and Allison have hit that point where their relationship moves ahead, by meet each others friends. But neither felt like they had made a great impression.

Gary ends up in Vanessa's doghouse after finally taking her on a real date, but brings her to a restaurant that he used to frequent with Allison.