Alan gives Lyndsey the option of choosing between him and Larry by proposing and Lyndsey turns him down. He goes to visit his ex-wife Judith and after they get drunk he proposes to her and she accepts especially after seeing the size of the ring Walden had given him. Walden sees how badly Judith still treats Alan and he tells Judith that she was the second person that Alan had proposed to that night causing Judith to break up with him. Meanwhile, Jenny is depressed that Brooke seems to be pulling away from her. After advise from Walden, she decides give Brooke a romantic gesture. She sets herself up in an S&M situation in Brooke's bedroom and gets discovered by Brooke and her parents.