Jay is a smart, confident reporter-in-spe, who is going into his sophomore year at Northwestern. He works as an intern at CNN and was the former editor of The Blaze. He is also a member of the Republican Party and is spending the summer covering the RNC in Houston for CNN.
Jay and Andrea worked together on the Blaze and have reconnected and start dating at the beginning of summer 1992. He meets the gang when going to The Peach Pit to take Andrea Zuckerman out on a date to see Batman Returns. He and Andrea go on dates and Andrea is surprised to learn that Jay is a republican, as she is a "card-carrying liberal", but it doesn't deter their romance in any way. Jay asks Andrea to join him in Houston for the summer, where he has gotten Andrea an internship at CNN as well.
They were falling for each other with Brandon Walsh watching on with jealousy. However, after Andrea formed a relationship with a young deaf boy, Cameron Shaw, she decided she couldn't leave him behind and turned down the internship. Jay left Beverly Hills to got to Houston, but agreed to a long-distance relationship with Andrea. At Christmas he broke up with her in a letter, which led to a very brief kiss between Andrea and Brandon.
- Jay sensed something between Andrea and Brandon, and actually asked Andrea if her decision to stay in Beverly Hills for the summer had something to do with Brandon.