Gary's ex-wife has gotten engaged and he finds himself trying to navigate fatherhood and his own new love interest.
When Gary changes clothes in front of Allison, they realize that they are acting the same way they did when they were married. They decide that they need to create some new boundaries in their relationship.
Gary realises 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 threatens to reveal the risque photographs Allison once gave to him, if she doesn't return his pool table.
When Allison and Vanessa start being good friends, Gary tries to break them up so Allison doesn't taint Vanessa's impression of him.
Gary decides it's time to get to know Vanessa's friends after Allison throws a party to meet all of Krandell's friends, but both fear that their first impressions didn't go over as well as they could have.
Gary takes Vanessa out on a real date to a very special restaurant, only to find out that it is the same one he and Allison used to go to quite often.
Gary and Allison pretend that they are still married when attending their friend's vow renewal ceremony, after much begging from Allison. However, Gary has a hard time following through once he gets there after he is tempted by a beautiful new divorcee.
Gary and Allison butt heads over where to host Thanksgiving. Allison tries to have everyone over her house including her parents, whereas Gary wants to have everyone at his house for his first Thanksgiving as a single dad.
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 decides to create a new bond with his son after seeing Krandall getting on so well with Tom.
Gary decides to prove men don't only want to date pretty women by dating Louise's regular looking teacher.
After Allison accidentally floods the first floor of Gary's house, she allows him to temporarily move back in with her.
Gary starts to panic after he and Dennis' sister start spending a lot of time together, and share a brief kiss, which prompts her to start to smother Gary and Dennis to start talking about the two of them getting married.
Gary learns a lesson about never mixing family with business when he gets faced with an audit from the IRS and needs to lean on Allison's brother for financial support.
Much to Allison's anger, Gary uses his 'veto', that he and Allison get to use once a year, to stop Louise from taking Chinese lessons because he feels she has to many extracurricular activities. But when Gary signs Louise up for golf lessons, Allison ends up using her veto.
Gary, annoyed with how much time Allison is spending with him at his house after breaking up with Krandall, plays match-maker and tries to find her a new boyfriend.
When Gary's bowling team makes the championship, he tries to motivate them. But when one player quits the team right before the championship game, Gary struggles to find a replacement.
Gary is forced to become the adult when his half-brother Mitch moves in with him after returning from the war and causes him to lose control of the kids and the house.
When Gary fixes Allison's garbage disposal, he and Allison find each other in the bedroom repeatedly.