Dean was a pretty awesome first boyfriend for Rory Gilmore on Gilmore Girls . He built her a car, watched TV with her and her mom, was a total sweetheart, and, even better, he looked like Jared Padalecki. What's not to love? Sadly, the older Rory got, the less compatible Rory and Dean became. She was on the Ivy League fast track, while he married young and decided against college altogether. When they did reunite, it was a total disaster for the both of them. Their lives diverged after that — Rory went on to have other loves and adventures, and Dean just sort of disappeared. Of course, outside of the show, that's because Padalecki was (and still is) busy playing another iconic The WB/The CW character, Supernatural's Sam Winchester. As a diehard Gilmore Girls fan for life, though, I can't help but think of every crazy possibility for Rory's love life — and, weird though it may sound, I sort of really think Sam Winchester and Rory Gilmore would have been magical together in some amazing alternate universe.
(I'm going to blame those gorgeous Gilmore Girls reunion photos featuring Padalecki and Alexis Bledel's adorable faces so close together for my sudden epiphany.)
Their relationship would have been complicated for sure. I mean, he's a hunter, she's a Gilmore. They have very different lives — but they are also both smart, talented people who put family first. Sam has had his ups and downs what with all the various demon possessions and all, but at the end of the day, he's a solid guy. And, like Dean, he looks like Padalecki.
I think Rory and Sam would have made an excellent pair, and here's why you should too:
They're Both Crazy Driven
Sam bounced around his entire childhood, but he was committed to going to college the whole time — and he worked his butt off to make it happen. He was on his way to law school before a certain yellow-eyed demon killed his girlfriend, and even now, he is committed to being the best hunter he possibly can be. His commitment would woo Rory, who is similarly unstoppable when she sets her mind to something. This is the woman who knew she would go to an Ivy League school when she was still in diapers, after all.
Sam Would Be Rory's Intellectual Equal
There is nothing more valuable to someone who talks as much as Rory than to have someone in her life who can keep up. Sam would totally be that person. He knows dead languages and obscure facts, and his wealth of arcane knowledge would be something Rory was totally into. Their brainy conversations would be the best kind of nerdy foreplay.
Family Is Everything To Sam And Rory
Are there two people more committed to their families than Rory and Sam (besides Lorelai and Dean)? I don't think so. They would both immediately understand why the other was so close to their family, and love each other more for it.
Sam Would Make an Excellent Long Distance Boyfriend
Logan offered Rory a "normal" life with a house and her own lemon tree, but she didn't want normal — she wanted amazing. For Rory, that meant hitting the campaign trail as a journalist. Her life is destined to take her all over the place, just like Sam's. Neither one of them would demand the other settle down because long distance living and occasional hookups would fit into their transitory lifestyles perfectly.
Rory Likes A Project
Ignoring Dean for a second, Rory loves guys who are emotionally damaged. Jess, Tristan, Logan — to some extent, they were all projects. They opened up Rory's world and she made their's a little more secure. Sam has some serious feelings of inadequacy and guilt that he needs to work through. I'm not saying it's healthy, but that would definitely be like catnip for Rory... as long as Sam didn't wallow too much, because Rory so would not have time for that.
They Would Make A Good Team
Sam and Rory would balance each other out in all the right ways. She would bring some much-needed lightness to his life, and he would expose her to a whole new world. Just imagine them consulting on stories and cases together. Rory would be a cooler version of Kolchak, and Sam would always have her back because he is incredibly loyal.
So, now that I've convinced you all, I ask: Who do I need to call to make this happen?
Images: The CW; Giphy (5); missmegrose/Tumblr
