He later returns in "Live to Fight", where Jessica seeks him out in order to protect herself, as she requires an attorney whom she can trust wholeheartedly. After helping Jessica by having Mike destroy an incriminating piece of evidence against her, Jeff decides not to be her attorney anymore; however, he hints that they may renew their relationship once this case is done and over with.
He encounters Jessica again in "Borrowed Time", where he expresses the fact that he is still interested in her; however, he tells her that he is moving to Chicago and knows that Jessica would not come with him, as she wishes to stay in New York and revive her firm. However, when Jessica steps down from the firm in "P.S.L.", she asks to come to Chicago with him and he accepts.