S4, E13: Stranded in Stars Hollow while his car is being repaired, Jess (recurring guest star MILO VENTIMIGLIA) keeps crossing paths with Rory--but he walks away from her every time. Luke tries to talk to Jess about Liz (recurring guest star KATHLEEN WILHOITE), Luke's sister and Jess' mother, who is dating someone new. However, Jess angrily tells Luke to stop interfering in other people's lives. Lorelai does a favor for Emily by attending a charity dinner and is pleasantly surprised when her secret boyfriend, Jason, arrives--and the unsuspecting Emily asks them to "pretend" they are a couple. Meanwhile, when Rory and Jess encounter each other for a third time, Rory tries to be the one who walks away, but Jess stops her and makes a shocking confession.