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Along the way, both of the titular Gilmore Girls find and lose love — so who does Rory date? Thankfully, the show got a Netflix revival in — "A Year in the Life," spread across four seasonally appropriate 90 minute "episodes" — to clear up some lingering questions about Lorelai and Rory's respective romantic prospects, but there are still some mysteries about who Rory ends up with after the revival comes to a close.

With that in mind, let's go over all of Rory's boyfriends on "Gilmore Girls," look at the timeline, and see where she ends up in the final, autumnal installment of "A Year in the Life. Just as soon as she's all set to leave Stars Hollow High School for Chilton Academy, Rory literally bumps into Dean, a tall and ostensibly handsome boy new to the small town — and sparks fly right away.

Despite going to different schools, the two start dating early in Season 1 of the series, but break up abruptly on the night of their three-month anniversary when Dean tells Rory that he loves her and she doesn't say it back. They reunite in the season finale and date through Season 2 and break up in Season 3 after a new boy comes to town and captures Rory's attention more in that shortly , but unfortunately, they reunite in Season 4.

Why is their reunion so unfortunate? In that season finale, while Lorelai celebrates the opening of her very own inn, Rory and Dean sleep together for the first time ever even though he's married, causing a major rift between Rory and Lorelai when the latter comes home and finds them getting dressed. Dean and Rory try to date for a while, but it doesn't work with her at Yale and him in Stars Hollow; eventually, they realize that they come from different worlds and want different futures, and they finally break up for good.

In Season 2 of "Gilmore Girls," Jess Mariano — the nephew of local diner owner and Lorelai's future boyfriend Luke Danes, played by Scott Patterson — comes to live with Luke in Stars Hollow, and despite Jess' decidedly bad attitude, his obvious intelligence and undeniable good looks charm Rory pretty quickly. The problem is, she's still dating Dean — who hates Jess — so aside from a spontaneous and surprising kiss in the Season 2 finale, Jess and Rory mostly keep their distance from each other.

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Rory and Jess don't really waste any time; a few episodes later, they're definitively dating. Milo Ventimiglia left the series at the end of Season 3 — despite the fact that one of the season's final episodes, "Here Comes the Son," is a backdoor pilot for a Jess-centric show that was clearly never picked up by The WB — so Jess and Rory break up , but Jess returns a handful of times.

In Season 4, Jess briefly returns to Stars Hollow, tells Rory he loves her, and begs her to run away with him only to get turned down , and after that, the two fall out of touch for quite some time. Thankfully, Jess shows up when Rory needs his wisdom the most in Season 6; upon finding out that Rory dropped out of Yale, Jess is furious with her and criticizes her for wasting the opportunity and her potential.

Thanks in large part to Jess, Rory ends up returning to Yale, and she goes to see him in Philadelphia to thank him for his support. The two share a kiss, but because Rory is still in love with someone else, the situation doesn't go any further and the two leave things on good terms.