Gilmore Girls fans have been debating for years now on who they feel star Rory, played by actress Alexis Bledel, should have ended up in a relationship with when all was said and done. During the popular series that ran from 2000 to 2007, Rory had relationships with three main men: Dean (Jared Padalecki), Jess (Milo Ventimiglia) and Logan (Matt Czuchry), each of whom offered something very different to Rory. However, when Bledel was asked during an interview on Watch What Happens Live With Andy Cohen on who she feels her character should have ended up with, she gave a very open-ended answer.
"Jeegan?" she responded according to Entertainment Tonight, combining the names of all three men. "I can't single somebody out," she added. Fans will remember, Dean was Rory's first love that she met in high school. After several years together, Dean quickly became a fan-favorite as he treated Rory well and with respect. The two characters also had quite a bit in common. However, once Jess stepped into the picture when he came to stay with his Uncle Luke (Scott Patterson), Rory quickly second-guessed on whether she wanted to stay with Dean forever.
Jess had a bad-boy vibe and found himself getting in a lot of trouble around town. He also became unfavored by almost every person in town; he was quite the opposite of Dean. But that didn't stop Rory from being intrigued because while they were very different in a lot of ways, they both had an appreciation for books and storytelling, which is what piqued her interest in him in the first place. Breaking up with Dean to hop in a relationship with Jess was not something the townspeople of Stars Hollow, along with her mom Lorelai (Lauren Graham), were on board with. But she did it anyway.
By the time Rory found herself in college, she developed a new love interest with Logan, who was a guy that came from a lot of money and almost combined qualities of both Dean and Jess. Logan was great to Rory, but also enjoyed living on the edge, which gave her enough of what she found in Dean and added a little spontaneity to the relationship with qualities she found in Jess. For years, it's been an ongoing debate among fans on who she should have ended up with because she ultimately found herself single by the time the revival took place in 2016 on Netflix.
While Bledel couldn't give a definitive answer, both Padalecki and Ventimiglia had a few things to say about it with each favoring the other. The Supernatural star said he was team Jess, while the This Is Us star said he was team Dean. Fans may never know who Rory ended up with or if she found someone new, but the mystery of it all is also what remains the most intriguing.