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 gives Shane a brotherly push to tap into his hidden potential as a skater by entering him into an amateur skating contest. Ryan finds himself anxiously watching his brother compete and questions if this was the best idea. Meanwhile, a friend of Taylor's recently separated from her boyfriend, causes Ryan to see her in a whole new light.

Since turning pro at age 14, Ryan Sheckler's career has been managed by his mother, Gretchen. Lately Ryan has become frustrated by the blurred lines between his mother's two roles and it's been causing conflict between them. What's a kid to do when his mom is his manager? Now that things are beginning to heat up with Kayla, Ryan isn't happy about leaving town for an event in Texas. Once again, he fears that his career may get in the way of yet another budding romance.

The Sheckler empire is expanding by leaps and bounds and there are a lot of concepts and language that Ryan is expected to understand. It all may be a little too much for the 17-year-old budding businessman. Even with having his hands full growing a business, Ryan finds his mind constantly drifting to thoughts of Kayla – the girl who puts him in the unusual position of being the one waiting at home while she’s 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 searches for a way to reconnect with his father and squash the silly arguments they keep having. Having just come off a trip to the Dominican Republic, Ryan is ready to spend some quality time at home, especially with his new girlfriend, Kayla. Dates and double dates abound as Ryan hangs out with Kayla, Casey and Taylor, leaving Tony to feel like a fifth wheel.