Gary Unmarried

Gary decides to call up his old friend Curtis who works at a local radio station, and is thrilled that he is offered a job, thinking he is going to become the next sports newscaster. Allison asks Gary to set a better example for the kids when Tom is happy with his low scores on a career aptitude test. Louise is escorted to her first dance class by Gary’s brother Mitch.

When Allison’s new boyfriend Howard, who happens to be very wealthy, offers to take Louise and her friends to New York for her birthday, Gary gets in over his head and promises Louise an unrealistic gift.

Gary tries to get Sasha to listen to his demo tape in the hopes she will let him become the new sportscaster. Meanwhile, Louise protects Tom from a school bully.

Gary, Curtis and Mitch decide to have a boy’s night out and go to a single’s club. While there, Gary is determined to prove to his friends that he can handle a one night stand without getting attached.

When the radio station’s sportscaster is arrested, Sasha needs to replace him and give Gary his radio debut. Meanwhile, Louise makes a video of well-wishes for Uncle Mitch and his Marine Corp. unit as a part of her schools volunteer week.

Gary finds out that dealing with two careers and two kids is harder to do than he thought it would be.

Allison gets upset when her new friend Sophia prefers spending time with Gary than her.

Gary has to put his tail between his legs and go running to Allison, after he fails to properly prepare Thanksgiving dinner for his family and friends.

Gary’s hands are full when he allows Louise to attend a party with the "popular" kids at the skate ranch and is keeping it a secret from Allison. Meanwhile, Allison grounds Tom for using profane language. Sasha decides to go shopping with Gary when Louise asks for clothes.

Sasha wonders whether dating a married man is worth the hassle, after Allison gets in the way on their date.

Gary helps Tom impress a girl by buying a boat. He begrudgingly has to go to Allison’s boyfriend for help when it doesn’t go as he had planned.

Tom begins mixing with people Gary and Allison don’t approve of, so naturally they have to pry into his life. Sasha becomes fond of pro surfer Laird Hamilton.

Allison teaches Tom a life lesson about being responsible, and Gary and Sasha get more serious so Gary worries about the repercussions of dating his boss.

After receiving a great Valentine’s Day gift from Sasha, Gary tries to top his gift for her. Meanwhile, Allison tries, and fails, to bond with Louise and Tom.

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

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.

When Gary finds out that he and Allison’s divorce papers were never filed, he uses the information to manipulate her into giving him his stuff back. Meanwhile, Allison’s sister Rachael comes to town and gives Mitch a makeover.