Ashley brings us into his very tiny apartment, who he is now sharing with his pregnant girlfriend and her mother. He visits his former bandmate, Jacob Underwood, in his nice home and they remember the times they had in O-Town.
Ashley and his girlfriend Tiffany are moving into their new home. Ashley confronts his producers for not being supportive of his decisions for his music career and that their relationship has shifted.
Ashley and Tiffany find out that they're having a premature baby and the doctor suggests she gets bed rest. She leaves the house and Ashley gets worried when he tries to call her but only gets her voice mail.
Dan Miller visits Ashley because he is in town doing a tour. They find out the show is cancelled and they are crushed. They watch their O-Town and reminisce their days. Ashley has a garage sale to try to make some money. Tiffany surprises Ashley to celebrate his 24th birthday. Another O-Town member, Erik-Michael Estrada, comes as well
The big day arrives, and Tiffany, Ashley, and mom all head to the hospital to welcome the new baby. After a hard labor, the new parents welcome a bouncing baby boy named Lyric, only a few days after Ashley's birthday.
Ashley proposes to Tiffany.
Ashley and Tiffany take a night out on the town for the first time since Lyric's birth with a few friends. Tensions mount in a crowded bar when a guy starts a fight with Ashley. The fight turns physical outside, and Tiffany steps in.
The ladies of the house sit Ashley down, and formulate a "Chore Board" for him to follow, he agrees to follow the board, without being told. Trevor shows up, and the guys take a wild night out on the town, and a wasted Ashley passes out with Trevor's help, without doing his chores. Ashley's manager schedules an open mic night at a local club
Ashley is out of sorts with all of the stress that he is under, so Tiffany surprises him with a visit from his mother. His managers offer the couple a weekend in Las Vegas, all expense paid, so the couple persuade mom to watch Lyric. Before the limo even pulls away from the curb, Ashley double dares Tiff in front of their friends to go ahead and marry him in Vegas.
As the first season comes to an end, Ashley is putting the finishing touches into his new album. He's come along way since O-Town and starting on the new album, but he still has several things to accomplish. With the new single, "Let U Go," coming out soon, he learns he must go on a six week radio promotional tour; Tiffany isn't thrilled about this because she and Lyric can't go with him. This causes tensions between Ashley and Tiffany