Winning Isn't Everything is the 5th episode of Young Americans.
Scout (Mark Famiglietti) is excited about uniting Bella and his father (Kate Bosworth, guest star Beau Gravitte) during Parents Weekend, while Jake (Katherine Moennig) must hide her charade from her mother (guest star Laura Sheaks); Will (Rodney Scott) reaches out to his father.
Scout visits Bella. When he returns to work, he drops his cell phone. Bella answers an incoming call from Senator Calhoun. Later, Scout tells Bella their father is coming to the Regatta and suggests she meet him, but Bella declines. Meanwhile, Jake (Jacqueline) receives an email from her mother, informing her she will be coming for the weekend. She rushes to tell Hamilton, who says if her mother finds out, Jake will be kicked out of Rawley and he will never get to see her again. Will meets Senator Calhoun, then brags to his mother how impressive he is, but she sticks up for Will's father. Hamilton is mesmerized when he sees Jake in a dress. Scout tries to convince Bella to meet their father again, but she refuses to meet him.