Riley plans to attend her family reunion in Orlando, but since she hates to fly, she decides to take the train instead. Ben realizes this trip is the perfect opportunity to rekindle their romance and volunteers to tag along. However, when Riley thinks he's only after one thing, Ben manages to convince her that his feelings are genuine. Can she bring herself to trust him with her heart once again? Meanwhile, Tucker has the chance to be Mary Hart's co-host and asks Bonnie for help with his audition tape. But when Mary decides to give Bonnie the job instead, Tucker is forced to play dirty in order to eliminate the competition.