For the month of December – in honor of Dressember – I’ll be blogging everyday! Thoughts on anything from fighting for justice to feminism, from dresses I’m wearing to books I’m reading, and everything in between. 

I’ve told you why it’s the best show in existence, I’ve explained why I’m obsessed with Lorelai. But let’s be real – the question everyone discusses when Gilmore Girls is over is who does Rory end up with??

I feel like we see Rory date every girl’s dream (which is probably what makes the show so addicting): the kind, sensitive one who happens to be the cute jock, the mysterious bad boy who happens to love classic literature, and the rich playboy who happens to fall for only her. Swoon. To all three. But with three so very different guys, who is Rory’s Mr Right?

Sidenote: this is my final Gilmore Girls themed post, for those of you who were wondering when I got hired by the CW to promote a ghost of TV’s past… (or the WB for all you original GG fans out there!)

Via foreveryoungadult.com (who’s similar analysis I totally disagree with, but is interesting)

Dean?
Um, no. Just no. When they dated in high school, Dean was kind and caring. He helped out around the house and hung out on the couch with Rory and Lorelai. He even stepped way out of his comfort zone and took Rory to her fancy Chilton dance. Sweet, sweet boy. But he was also a pushover, too clingy, and (how do I put this nicely?) not on Rory’s level. When Jess was winning Rory over behind his back, Dean basically sulked and let it happen. What?!
And then sweet Dean becomes idiotic Dean and marries a girl (who seems like a rebound) right out of high school. He finds himself in an unhealthy, manipulative, too-much-pressure not-enough-communication marriage and what does he do? Run to Rory. An emotional affair leads to an actual affair, and Dean’s marriage is over – with Rory in the middle of it. (Not diminishing Rory’s part to play in it all – she was way out of line.) Not only is Dean emotionally immature and unable to voice his needs, he allows life happen to him – rather than going out and making things happen. Definitely not the kind of man Rory needs.

Jess??
I have so many friends who are Team Jess. Too many friends. That’s because – as with every bad boy – people are obsessed with his potential and not his reality. What we want to focus on: his mysteriousness, his love for books, his feelings for Rory. What we want to ignore: he lies (a lot), he fails high school, he has anger issues, he’s flaky, he only thinks about himself, he treats Luke like crap, he treats Lorelai like crap, he treats Stars Hallow like crap, annnnd he treats Rory like crap.
When you grow up, you realize that bad boy is really just short for “bad boyfriend”. Jess messes with Rory’s emotions – while she’s dating Dean and even when she’s finally with Jess. He flat out refuses to do anything that doesn’t interest him – dinner with her grandparents, Chilton events, Stars Hallow celebrations. You know, those things you usually bring a boyfriend to. He’s MIA basically all the time, until he’s actually literally MIA and FLAT OUT LEAVES WITHOUT SAYING ANYTHING. Are you kidding me!? Messed up on so many levels – but especially to someone as amazing as Rory, who you fought so hard to get?? Ugh. Grow up, Jess.
[Which, he eventually does! He writes a book. He makes something of his life. He apologizes to Luke. Future Jess has potential, and Rory sees that! But she also runs to him when things with Logan are weird, which isn’t healthy. Future Jess is a million times better than high school Jess… but still doesn’t mean he’s the one for Rory.]

Logan?!
Logan is tricky – because you start out completely hating him, and then you find yourself starting to think he’s actually endearing and thoughtful, and then by the end you aren’t even sure what Rory should decide! One thing is for sure: when Rory turned him down (which, who proposes out of no where?? Have a timeline conversation, buddy), and he ended things on the spot, it was obvious she made the right choice. Don’t try to force an ultimatum on a girl on her graduation day!
Logan comes a long way, that much is obvious. He cares enough about Rory and about keeping her in his life that he makes a lot of personal changes – that’s admirable. But that doesn’t necessarily mean he’s worth it. He’s incredibly immature, he loves playing the victim, and he never takes responsibility for his actions. Rory put up with so much while she was with him, and although relationships do require compromise and sacrifice it seemed like she was the one doing both. Rory deserves way better.

Soo… who?
Call me a conspiracy theorist or crazed fan or obsessive, but here’s what I personally think happened: She doesn’t end up with any of them. Rory went on the campaign trail. She probably helped Obama win, let’s be real, because she’s Rory. She got hit on all the time and everyone wanted to know who the new, young, beautiful, brilliant girl was, but she wasn’t having it because she was still grieving her break up with Logan. (He tried to win her back a few times with extravagant gestures, she got really upset over it all and finally told him to STOP. 3 months later he’s married to a trophy wife his family had waiting all along.) Rory considered dating future Jess, who had matured a lot, apologized for the horrible person he was, and captured her attention again. But she realized that, great person he is, the attraction was built on high school romance, which isn’t sustainable. They find themselves as two completely different people, and a relationship clearly wouldn’t work out. She swore off men for a while (which Lorelai and Luke encouraged, obviously), traveled the world as the journalist she always wanted to be, and finally settled into her dream job (NY Times, duh). She ends up meeting an older Yale alum, who’s intelligence attracts her above anything else. He has the social graces of Logan (without the arrogance), Jess’ ability to question her and push her into new ways of thinking, and Dean’s kindness. He takes her on surprise adventures but also on weekend trips to Stars Hallow, he proofreads her column but also let’s her have her spotlight, and he loves her for all her Rory-isms. That’s the kind of man who (barely) deserves Rory Gilmore.