Gary comes to terms with the news of his ex-wife's engagement, while trying to navigate fatherhood and a new love interest of his own.
When Gary tells her about his sex life with his new girlfriend and then shows up and her house to use the hot tube while she's out, Allison decides they need new boundaries. Meanwhile, Tom has troubles with his new girlfriend.
When Gary thinks of all the toys he can buy once he stops paying spousal support, he tries to encourage Dr. Krandall to set a date.
When Allison refuses to return Gary's pool table since he gave it to her as a gift, Gary threatens to show everyone the racy photographs Allison gave to him on their first anniversary.
Gary tries to convince the two women in his life to stop being such good friends, fearing that Allison will taint Vanessa's impression of him.
When Allison throws a party to meet Krandell's closest friends, Gary decides it's time to meet Vanessa's friends as well, but both fear that they didn't make the best first impressions.
When Vanessa asks Gary to take her on a real date, he tells her that he's taking her to a very special restaurant just for them, which Vanessa discovers was the same restaurant he and Allison used to frequent.
Allison convinces Gary to pretend they are still married for their friend's vow renewal ceremony, but Gary struggles to keep their secret when he is tempted by a gorgeous new divorcee.
A territorial battle breaks out between Gary and Allison when Allison tries to have everyone celebrate Thanksgiving at her house, and Gary tries to lure the whole family to his house for his first Thanksgiving as a single dad.
When Gary learns that Allison plans to take the kids to their first concert, he gets concert tickets for the night before. This leads to a battle of "firsts" with both parents rushing to expose Tom and Louise to new experiences first.
When Gary feels threatened by Tom's relationship with Dr. Krandall, he goes to great lengths to change this dynamic and bond with his son.
Gary asks Louise's less attractive favorite teacher on a date in an attempt to prove that he doesn't only date pretty women. However, he finds himself double booked since he already asked out her other more attractive teacher.
When the first floor of Gary's house is accidentally flooded, he is forced to temporarily move back in with Allison. Walter is jealous and eventually Alison realizes that she is not ready to get married.
Gary panics when he and Dennis' younger sister, Anna, start spending time together and after only a week, Dennis starts talking marriage.
Gary learns the lesson of never mixing business with family when he is forced to lean on Allison's brother for financial guidance after he is faced with an audit from the Internal Revenue Service.
Much to Allison's dismay, Gary vetoes Louise from taking Chinese lessons fearing she has too many extracurricular commitments, but when he tries to enroll her in golf lessons, Allison pulls out her veto.
Gary tries to find a Allison a new boyfriend after she starts spending too much time at his house.
Allison starts showing up at Gary's house everyday following her breakup with Krandall, which forces Gary to play matchmaker in order to find her a new love interest.
Gary tries to motivate his bowling team when they make it into the championships, but instead finds himself searching for a last-minute replacement when one team member quits.
When his rambunctious half brother, Mitch, returns home from the war and decides to move in, Gary quickly loses control of his kids and his house and is forced to play the role of a grown up.
When Gary stops by Allison to fix her garbage disposal, their deprived love lives gets the better of them and they find themselves in Allison's bedroom.
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