Though it always felt as though Luke and Lorelai were endgame, it was always a whirlwind game of what would happen romantically with the youngest Gilmore Girl. Over the course of Gilmore Girls ' Rory Gilmore had three significant boyfriends, each boyfriend marking a different side of her, and a different time in her life. So considering how open-ended the series finale was, we can only imagine how Rory's life would have been if she'd ended up with Jess, Dean, or Logan.
That said, I want to be perfectly clear that I didn't do this to weave a bunch of happily every afters for your favorite couple. Rather, I looked at where we left these pairings off, where the relationship looked like it was going, and retconned back to the point of break-up if necessary. So, these are strictly my scientific educated guesses of what would happen, with only... minimal bias. If you need to believe it would work out with your favorite pairing, well — that's what Fanfiction.net is for.
In any case, enjoy these three theories of what would happen if Rory ended up with one of these studs.
What if Rory ended up with... Dean?
Though Rory's life and times at Yale put a strain on their relationship, she trudged on awkwardly with Dean, eventually putting the nail in the coffin with an unexpected pregnancy in her senior year. Dean wanted to avoid another quickie marriage, the couple mutually decided to raise their daughter together-but-separately — as a couple, but not husband and wife. Things became difficult on that end, with Dean juggling freelance construction jobs, and Rory working on her mommy blog and staying home with their brunette daughter, Lei-Lei. Lorelai IV, technically.
Lei-Lei, for the record, is an insufferable brat and straight-C student, who proves that rocky mother-daughter relationships skip a generation with the Gilmore girls. This wayward child, their lack of funds and Dean's affair with Miss Patty, has deeply estranged them. One day Rory wakes up and realizes she's donning funky wrap dresses and 4-inch heels, being touted as the "hot young mom" at Stars Hollow High.
"Oh god, I've become my mother," she realizes, secretly more upset than she'd ever admit.
It could be worse, though. No matter how terrible things are, staying in Stars Hollow allowed for the constant support of Lorelai and Sookie, and it kept her close with Lane, who made her own bad decisions at the age off 22. In fact, every once in a while a girls night in is order: They watch kitschy old films and share a bottle of wine, lamenting the way their lives turned out.
"Whatever happened to Dave Rygalski?" Rory slurs one night.
"Zack's still Facebook friends with him — apparently after he moved to California he really made it big," Lane slurs back, spilling merlot all over her sweater.
What if Rory ended up with... Logan?
Though she knew she'd have to sacrifice some of her ambitions, Rory accepted Logan's proposal. After all, this was a man who inspired her more adventurous side, so by making this journey with him, wouldn't she be embarking on another adventure? Yes and no.
Rory had to plan her wedding while following around the Obama campaign, and though the stress was enormous, it initially seemed worth her efforts. Their first year of marriage was a whirlwind of trips to Monaco and Bali, with Rory returning to Connecticut looking perpetually tan and glowing. But, in time, the honeymoon was over, and a pallor clouded over Mrs. Huntzberger.
Logan started going on business trips solo. Rory worked as an editorial assistant for The Advocate until the recession took it's toll and she was laid off. Since then, tensions have been high between the two, and though they handle high society functions like pros, they always go home and have some melodramatic fight.
Glasses are shattered. 4-letter words are thrown around. (SAT words are also thrown around, because Rory has to prove that she's well-educated.) And, the next day, Rory meets Emily for brunch and Emily still wonders why Rory isn't giving her great-grandchildren yet.
"It's not like you're doing anything else," she muses, while Rory massages her temples, on the verge of a migraine.
What if Rory ended up with... Jess?
Jess and Rory reconnected in 2010 at the Union Square Barnes and Nobles in NYC, where Jess was doing a book signing for his second full-length novel. Suffice to say, it did well... not Stephen King well, but you know, well enough where a movie deal was being worked out with an independent production company. Rory was doing well, too... not Christiane Amanpour well, but well enough to have a stable job as a reporter for New York Magazine's Vulture. The timing seemed right, so they decided to grab a coffee and catch up. They've been together ever since.
Of course, it's not easy. Two writers trying to make rent for a brownstone on the Upper West Side? No matter how many Random House book parties they attend, or how many Twitter followers Rory gets for her rapid fire quick wit, there are some months where, yeah, Rory has to dip into the Richard and Emily fund. Sometimes Rory's poor impulse control shows itself, like when she brought home a Scottish Terrier to love. Sometimes Jess's temper comes back, like when Rory brought home a Scottish Terrier to love.
But they make it work, because their relationship was worth the wait. The duo and Black Francis (yes, after the Pixies' frontman) live a very happy life.
Images: CW (1) Getty/Mary Grace Garis (3)