In Season 5, Episode 7, Vince and crew show up to Vince's latest gig... a modeling job for Dolce & Gabbana. Vince and Natahsa really hit it off at the party and everyone notices, including jealous Frederick "Freddy" Lyne. Meanwhile, Ari is at Alan Gray's funeral and when he approaches his boss, John Ellis (Alan Dale), about smoke jumpers, he gets offered a job as the studio head.
Back at the photo shoot, Natasha is replaced with a new model and Eric gets some very positive attention from Raina, who it turns out is just looking for E to be her manager. Freddy reveals he wasn't jealous of Natasha, he actually wanted Vince. Vince then quits and gives up the $1 million pay check. John Ellis continues to try and convince Ari to leave his agent life and sends him the world's finest watch and an invite on his private jet to Geneva.
Vince gets his own invite on a jet by Natasha and her beautiful friends as the guys go to join them on their photo shoot. Vince and Ari end up leaving on seperate jets out of the same hanger in Van Nuys. Vince congratulates Ari on his new job but says he would have liked to have finished what they started. What will Ari choose?