When a friend of Gavin's a writer shows up and tells Gavin that he wrote his book and he comes to Gavin looking for support because Gavin's the only writer he knows who's been published. He wants to know how to deal with all the hype. And when he goes on how promising it is, it makes Gavin feel bad because he hasn't written in a long time. So he tries to write again.
When an iPod is found in the bookstore and when Gavin looks at the songs in it and sees that they're songs he likes, Skylar makes him think that the owner could be his soul mate. When a young woman comes to claim the iPod, Gavin asks her out and just when things are getting heated, her parents arrive and she reveals how old she is.
Skylar offers to clean out Gavin's closet and among the things she chooses to throw out is his cowboy boots. Katrina is pining after a guy who comes in regularly and when she can't find the courage to talk to him. Skylar decides to throw a Western theme party which has Gavin fuming cause she threw out his boots.
After Katrina and Stuart spend the night together, they go in to work and are not sure what to do about it. Gavin is concerned how this could affect the business, because technically, they are her boss and what happened could be construed as harassment.
When Gavin learns he has to go to the hospital for minor surgery, he freaks out. He tells Stuart where his will is, just in case. Stuart looks at the will and is shocked to discover that Gavin is putting his wife in charge of the bookstore. He asks Gavin to let him take care of the bookstore but Gavin doesn't think Stuart can handle it. At the hospital when Gavin is being sedated he utters something to Skylar.
When Harold's daughter comes to introduce her new boyfriend. Harold doesn't exactly warm up to him. And rightfully so, the man's a hypnotist and he uses his ability to get Skylar to make out with him. And when Gavin sees this, he doesn't know what to do.
Gavin gets engrossed in online poker game. That's when his ex-wife shows up telling him he has to take their son for a haircut for his interview at the school they hope to get him in. But Gavin had already agreed to do it tomorrow and is doing so well at the game, he lets Skylar take him. But when they come back, the style he chose is not exactly what they hoped he would get. So Gavin dreads telling his ex what happened because he knows she won't approve of him choosing gambling over their son's welfare. And when a guy sits in Harold's chair, he tries to get him to ...
Gavin and his ex-wife bring their son to the school for his interview and they're worried that the haircut he got might not make a good impression on the head master. So they bring Skylar along who was the one who brought their son for his haircut to explain. But when the man meets her he can only think about hooking up with her. Later when they go to his place, he makes a move which she rebuffs. And when Gavin and his ex hear about it, they're worried this ruins their son's chances.