It's finally time for Ryan to move into his own home. Gretchen has been working diligently to get Ryan's affairs in order, but Ryan fears that his mom is taking over and his creative say will go unheard. After an argument between the two of them, Ryan comes to realize that his mother is actually working so hard as a way to distract herself from her emotions regarding her firstborn leaving the nest. Meanwhile, Gretchen reveals her recent split with boyfriend, Bruce, and Ryan is surprised when his dad shows concern.

Ryan tells Taylor that they need to take a break in their friendship while he travels to Los Angeles for interviews.

After Ryan's best friends Casey and Taylor called it quits, Ryan works to figure out how he'll keep his close-knit support group together. With Casey acting jealous, it makes it hard for Ryan to hang with Taylor and the two guys get into a fight. After working so hard taking meeting after meeting, Ryan will finally see the fruits of his labor: his line of t-shirts in stores!

Ryan is anxious about buying his first home and gets serious with Casey about figuring out their future as roommates. Meanwhile, the pro skater learns from Taylor that she and Casey have decided to go their separate ways. Ryan tries to console Casey but for some reason Casey won't open up to Ryan and Ryan tries to figure out how best to be there for his friend.

Ryan and his dad experience the single life after ending their relationships.

Ryan tries to win back his former girlfriend Cambria at the winter formal dance, and tries to figure out with which of his newly-divorced parents to spend Christmas.

After unsuccessfully trying to salvage his relationship with Julia, Ryan gets an offer from Taylor to be set up with one of her girlfriends. Also, Ryan and Shane get to meet their mother's first boyfriend after her divorce.

Ryan's family celebrates his little brother Kane's eighth birthday, but confrontation ensues when his recently-divorced father brings his new girlfriend to the party.

Ryan makes time for his little brother Kane, and they spend the day together. However, Ryan could be creating a problem when he becomes interested in a buddy's former girlfriend.

Ryan has the girlfriend he's been looking for within reach, but does he move forward with making the commitment? Meanwhile, important sponsor Plan B has another skate trip booked for the athlete in the Dominican Republic. When Ryan discovers Kayla's birthday falls on a day he's gone, he's forced to choose between honoring his professional commitment and being there for his potential girlfriend's birthday.