It's Halloween and Charles helps the kids prepare for the night. He also helps out Buddy who is lacking confidence over a date and wants Charles to 'accidentally' run into the girl and learn what she likes.

Douglas discovers love when he meets a strange friend of Lila's named Enid. He likes her the way she is and gets upset when Lila tries to give her a makeover.

In an attempt to improve their relationship, Charles and Gwendolyn decide to see other people. This arrangement works well until Gwendolyn gets a date and Charles finds himself jealous.