All of the times Jess comes back in Gilmore Girls (and what happens)

Ever since he made his first appearance in season 2 episode 5, “Nick & Nora/Sid & Nancy,” Gilmore Girls fans have been head over heels for Jess… and Milo Ventimiglia. Luke’s troubled nephew arrives in Stars Hollow to live with his uncle, and the unruly teen quickly makes his mark on the quiet small town. He especially catches the eye of Rory Gilmore.

The apparent connection (and attraction) between Rory and Jess causes some problems in her relationship with Dean, leading to their eventual breakup in season 3 during the dance marathon. After the fact, Rory and Jess officially start dating by the season’s Thanksgiving episode, but they don’t live happily ever after. Actually, their relationship is far from a fairytale.

In the penultimate episode of season 3, Jess travels to Venice, California to spend time and potentially move in with his father. The episode operated as a potential backdoor pilot for a potential Jess-centric spinoff series called Windward Circle set in California, but The WB didn’t pick it up to series. Regardless, Jess leaves town and leaves Rory heartbroken.

While the dust settles from their breakup and Rory gets her bearings at Yale, it doesn’t take long for Jess to return in the fourth season. Ventimiglia appears in four episodes of season 4, two episodes of season 6, and two episodes of A Year in the Life. Here’s a quick refresher to what happens each time Jess makes a comeback on Gilmore Girls.

Season 4 episode 12: “A Family Matter”

Jess first returns after season 3 in the middle of season 4. His return trip to Star Hollow involves getting his car back and coincides with his estranged mother landing in town, too. Liz (Kathleen Whilhoite) ends up back in her hometown for her high school reunion, and it’s the beginning of a very long family reunion for Luke. Later on in the episode, Lorelai and Rory discover Jess sleeping outside in his car in the cold after an argument. Luke ends up letting him inside to sleep.

Season 4 episode 13: “Nag Hammadi Is Where They Found the Gnostic Gospels”

In the following episode, Jess tries to avoid Rory while waiting for Gypsy to repair his car, but the exes keeping running into each other until they finally hash it out. Rory runs from him in the street but stands to face him as he tells her that he still loves her. She doesn’t have a chance to respond before he’s off again. It’s an interesting and unexpected moment that stays with Rory.

Season 4 episode 20: “Luke Can See Her Face”

Toward the end of the season, Jess comes back to Stars Hollow for Liz and TJ’s wedding, and when he discovers Luke’s self-help book on tape, he pokes fun at his uncle. However, Jess takes some wisdom from the book and seemingly realizes that he hasn’t been treating Rory in the way that he should have, especially if he actually loved her and wanted to get back together.

Season 4 episode 21: “Last Week Fights, This Week Tights”

In the following episode, Jess attempts to make good on this new realization and tracks Rory down at her dorm at Yale. He asks her to go away with him, which ironically goes against what he later tells her in season 6. (But the whimsy of young love, you know?) Around this same time, Rory had been reconnection with Dean. She turns Jess down in favor of Dean. This might be a hot take, but Rory shouldn’t have been deciding between her high school boyfriends in college.

Season 6 episode 8: “Let Me Hear Your Balalaikas Ringing Out”

After a total absence in season 5, Jess reappears about midway into season 6, just in the nick of time to talk a little bit of sense into Rory. No one had gotten through to her about leaving Yale and living in her grandparents’ world, but seeing Jess working with a publishing house in Philadelphia and writing a novel knocks something loose. Also, Jess and Logan tangle over dinner, which is telling, too. Still, “Why did you drop out of Yale?!” is an iconic quote.

Season 6 episode 18: “The Real Paul Anka”

When the publishing house Jess works with has an open house, he invites Luke and Rory (and also April) to visit. Jess thanks Luke for everything he did for him and even repays a debt, and it truly showed the full evolution of Jess. After the open house, Rory and Jess share a kiss, but she admits she loves Logan, even if she’s mad that he cheated on her. Jess doesn’t appreciate being caught in the middle, but still offers to let her use the kiss to get even with Logan. And that’s the final appearance of Jess in the original seven seasons.

A Year in the Life episode 3: “Summer”

Even though Milo Ventimiglia was busy with his Emmy Award-nominated role on NBC’s This Is Us, he made the time to make a few cameos in A Year in the Life. Jess isn’t in the first two episodes, but he finally arrives in the third episode to help Luke save Liz and TJ from a vegetable cult (naturally). Of course, he reconnects with Rory, and it’s said they hadn’t seen each other for four years, so potentially sometime in 2011 or 2012. During a conversation at the Stars Hollow Gazette, where Rory now works, he inspires her to write her life story.

A Year in the Life episode 4: “Fall”

In his next revival appearance, Jess visits Luke at the diner. He’s none too pleased that his uncle’s once cell phone-free establishment now has wifi and a sea of screen-obsessed customers. Jess further displays his growth and maturity by helping Luke with personal issues, and on his way out, he unplugs the wifi. King!

In his last scene in A Year in the Life’s finale, he’s at the Gilmore house helping Luke with wedding things when Rory informs him with excitement she’s started writing her book. Luke notices the renewed connection, but Jess insists it’s history. But that look before he leaves… He’s still got it bad for Rory after all these years.

All seven seasons and the revival miniseries of Gilmore Girls are available on Netflix!