Gary Unmarried follows the life of a recently divorced couple sharing custody of their kids while starting new relationships.
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.
When Gary disrobes in front of Allison, they realize they're still too familiar with one another. Determined to put some distance between each other, they set up new ground rules for their post divorce interactions.
Gary pushes Allison's fiancé to set a wedding date when he realizes that their nuptials will mean the end to his alimony payments.
Gary wants Allison to return his pool table and threatens to show off some racy photos she once gave to him if she refuses.
Allison and Vanessa's growing friendship is making Gary nervous because of its potential to color Vanessa's impression of him. To stave off any embarrassing revelations, Gary urges the women in his life to look elsewhere for female bonding.
Gary and Allison's new relationships reach a milestone: meeting the friends. But neither feels confident in the first impressions they made.
Gary honors Vanessa's request to go on a real date, but ends up in the doghouse when he takes her to the restaurant he and Allison often patronized.
As a favor to Allison, Gary pretends they're still married when they attend a friend's vow-renewal ceremony. But the plan goes awry when Gary finds himself attracted to a fetching guest.
It's Gary's first Thanksgiving as a single father, but with Allison hosting her own gathering, the exes find themselves competing for guests.
Gary tries to outdo Allison when he learns she is taking the kids to their first concert. He counters by planning to share significant life events with them such as helping Tom with his first shave and purchasing Louise her first bra.
Gary's plan to improve his son's physical education grade through a series of father and son sports seems only to drive Tom into a closer relationship with Dr. Krandall.
Louise pressures Gary into dating her favorite teacher, Miss Plummer, just after he's arranged a date with her hot substitute teacher, Miss St. James.
After Allison accidentally floods the first floor of Gary's house, she allows him to temporarily move back in with her.
Gary starts dating Dennis' younger sister, but he freaks out after learning that Dennis' plans for the couple's future involve marriage.
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.
Gary and Allison disagree on what kind of extracurricular activities Louise should be involved in. He wants her to take golf lessons, while Allison wants her to learn Chinese.
Gary plays matchmaker for Allison, whose breakup with Krandall has her hanging out at Gary's more than he would like.
Gary asks Allison to fill in a vacancy in his bowling team in order to win the trophy, but she's feeling put out because she wasn't asked to join when the team was formed.
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.
Both Gary and Allison are dismayed to find their frustrated libidos mean they can't keep their hands off each other.
Gary tries to inspire his lackadaisical son Tom by pursuing a career in sportscasting. A call to an old buddy at a radio station results in a job offer, but Gary is surprised when he learns what they actually hired him to do. Meanwhile, Mitch takes Louise dancing.
When Allison's new boyfriend Howard offers to take Louise to New York for her birthday, Gary gets in over his head and promises Louise an unrealistic gift.
Desperate to get the job as a radio sportscaster, Gary attempts to convince Sasha to listen 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 himself in over his head as he tries to balance handling two careers and his kids.
Allison's feelings are hurt when she realizes her new friend Sophia prefers spending time with Gary over her.
Gary tries to prepare an elaborate Thanksgiving dinner for Sasha, Curtis, his father and the kids, but he fails miserably and seeks Allison's help to save the day.
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 tries to help Tom impress a girl by buying a boat, but he gets in over his head and must seek help from Allison's boyfriend.
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.
Gary tries to one up Sasha on Valentine's Day with the perfect present. Meanwhile, Allison makes an effort to spend quality time with Tom and Louise.
Gary tries to get Tom a spot on the wrestling team by challenging the coach, who also happens to be his high school nemesis, to a match.
Gary tries to help Mitch find work after he returns from abroad. Meanwhile, Allison gets a job as Curtis and Charleen's wedding planner.
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.
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