Following repeated interactions in which Jen insists that they remain friends, the pair finally share their first kiss. Jen and Henry date for months before breaking up after the prom. They make up in the season finale. However, Henry breaks things off in season 4 after he begins attending a boarding school.

Does Jen get with Henry?

At the end of the season, Jen ends up choosing Henry, but Pitt exited the show because he reportedly felt the role wasn't challenging enough, so they wrote him off during the fourth season premiere, saying he broke up with Jen and went off to private school on a football scholarship.

Does Jen Lindley sleep with Henry?

Jen was courted by Capeside High's star freshman quarterback, Henry Parker and the two dated throughout most of Jen's junior year. Jen later entered a purely sexual "friends with benefits" relationship with Pacey; both agreed that there will be no emotion involved whatsoever.