Jimmy and Jill have been together on-and-off, but they still have feelings for each other. Jill proposes a way she and Jimmy can get back together. However, Jimmy’s friends and parents worry restarting this relationship may derail his future.
However, things have changed and they are happy together. In the fifth episode of the series, Jill proposes a romantic week away before he leaves for Alaska. On the other hand, Pags receives a letter from Brooklyn Law saying that he did not get in. He cancels his date with Juliana because he believes Juliana won’t like him if he isn’t going to law school.