Jonathan arrives in Beverly Hills on New Year's Eve 1995. Susan picks him up at the airport and brings him to her dorm. He comes to the New Year's Eve party at the After Dark where he smugly declares to Brandon Walsh that he is in love with Susan and is going to win her back. Although he mentions liking Brandon's writing for The Condor, Jonathan straight up tells Brandon that he is irrelevant to Jonathan and Susan's relationship. At midnight as 1996 rolls in, Jonathan kisses Susan and she briefly kisses him back.
As the details unfolded of Jonathan's and Susan's relationship, it became known that they broke up because Susan had an abortion after Jonathan got her pregnant. Jonathan was pro-life and did not approve of her decision. Jonathan was a skilled pilot and took Brandon Walsh, Steve Sanders, and Joe Bradley on a test flight. However, Joe had some issues with his heart after going on the flight and passed out, which cut short any future trips into the air.
In an attempt to get rid of Jonathan, Valerie Malone set him up with her old friend, Ginger LaMonica. The two concocted a deal to make Susan jealous, which ended with Susan punching Jonathan in the jaw. Jonathan continued to hang around trying to break up Brandon and Susan, but was ultimately unsuccessful. He later left town.