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 sets out to repair Allison's garbage disposal but find themselves inside her bedroom fixing their lust for sex.

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

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 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.

After a bowling teammate quits before the championships, Gary rushes to find a replacement.

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 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.

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 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.

When Allison breaks up with Krandall, she begins showing up at Gary's house, forcing Gary to find her someone new.

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.

When Gary discovers that Allison is going to take the kids to their first concert, a not-so-friendly competition kicks off. Gary tries to out-do Allison by exposing the kids to other first experiences, such as Tommy's first shave and buying Louise her first bra.

Gary begins to feel threatened by Tom's relationship with Dr. Krandall, leading him to change the relationship he has with his son.

Gary freaks out after learning that Dennis has made plans for his marriage to his younger sister, after they begin dating.

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.