Riley plans to break up with Fitch, but then receives the news that Fitch is dead. She meets Fitch's dad, Winston Douglas, who asks her to deliver the eulogy at the funeral and tells Riley that Fitch planned to propose to her. Meanwhile, Ben realizes he might be in love with Megan, but she thinks things are moving way too fast. Tucker embarks on his "Tucket" list of things to do before he dies and Bonnie schemes to catch the eye of Fitch's wealthy dad.

Ben's feelings are hurt when Riley wants to talk to Danny and not him about her bar exam woes, but she finally confides in him that she has taken the test three times without passing. Determined to support his friend, Ben tries to convince her not to give up on her dream of becoming a lawyer. Meanwhile, Bonnie finds out that Amy has taken a pregnancy test and struggles to keep the secret, while Danny tries to win over Amy's father, who clearly dislikes him.