Ryan is excited to move out into his own home, but the latest conflict between his parents makes him question the timing. Meanwhile, it's the final Dew Tour Stop in Orlando, Florida and Ryan relies on his friends and family's support as he strives to earn the title of Skate Park Champion for the third year in a row.

Ryan thinks its time for Shane to get more into skating so Ryan enters him into the Damn Am, an amateur skate competition. Shane isn't to confident about it though. Ryan starts to get feelings for a girl named Kayla and tells her they should hang out sometime.

Ryan and Gretchen clash when her role as mom and manager blur together. Now that things are beginning to heat up with Kayla, Ryan isn't happy about leaving town for an event in Texas.

Ryan is overwhelmed by his burgeoning business empire and dislikes being the one waiting at home while Kayla is away on business.

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.

Ryan tries to mend fences with his father and spends quality time with Kayla, Taylor and Casey, leaving Tony feeling left out.

The dog Ryan decides to buy is really not helping to bring the family together.

Ryan decides to throw a holiday party and Gretchen wants to do it at the house. Unfortunately, hosting it at Gretchen's means Ryan's dad can't come and Ryan has no idea how he'll give his father the crushing news. Having heard that the divorce court case has finally been settled, Ryan renews his search for a home of his own.

Ryan's family and friends throw him a surprise 18th birthday party.

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

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.

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

The day has finally come when Ryan hears that his offer has been accepted on the house of his dreams. Once the reality hits, a new issue arises – should Tony be another roommate? At the invitation of Red Bull, Ryan says Auf Wiedershen to San Clemente for the Alpine delights of Austria. He brings Tony with him and takes advantage of their time away to weigh out their housemate compatibility. Unfortunately, while Ryan works to charm one of his biggest sponsors, Tony can't stop complaining at every given turn.

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.