Much has been said about the recent news that all three of Rory's previous love interests will be returning for the Gilmore Girls revival. Whether you are Team Dean, Team Jess, or Team Logan, you can't help but be excited about this. Who doesn't love a good love quadrangle? Let's take a moment to dissect these men and their relationships with the youngest Gilmore.
Dean Forester: In essence he was the quintessential first boyfriend. He chased her, doted on her, and loved her unconditionally. It was a fairy tale beginning. He was new in town, incredibly tall, handsome, and a gentleman. But fairy tales don't last. Soon he began to show his clingy and jealous nature like when Rory decided to throw herself into philanthropic endeavors to increase her chances of getting into Harvard. Eventually he apologized for yelling at her (in public no less, something he did quite a few times actually), but it just proved his insecurities with Rory and himself. He blamed their failing relationship on Jess, but in reality it wouldn't have lasted anyways. That is proven by their horrible reunion in season four. It also showcased his not-so-great character (cheating on his wife should have been a red flag for Rory).
Jess Mariano: You either really loved him or really hated him. I wholeheartedly loved him and still do. A lot of people peg him as the stereotypical bad boy who just came in, broke Rory's heart, and left. This description is wholly inadequate and kind of false. Yes, he was the bad boy from New York who smoked, cut class, and pulled pranks on the town (and you're lying if you say the fake chalk outline wasn't funny). He was also incredibly intelligent, funny, and not to mention gorgeous. He was the only one of Rory's boyfriends that matched her intellectually and personality-wise. For goodness sake, he was the one who got her back on track at Yale when no one else could because he understood her better than anyone else. He never asked her to change herself, only pushed her to be the best version of herself possible, and she did the same to him. They just never had the right timing.
Logan Huntzberger: He was a great college boyfriend...sometimes. When he wasn't sleeping with bridal parties or jumping off mountains drunk, he was actually a pretty decent boyfriend. He offered Rory a place to stay when Paris kicked her out, she never had to worry or want for anything, and he broadened her horizons and gave her experiences she never would have had without him. But instead of just broadening her mind, he ultimately changed her personality - not for the better. She adopted his party lifestyle, dropped out of Yale (because of Satan himself - Mitchum), and worst of all stopped talking to Lorelai. Despite repeatedly proving that he couldn't be trusted, Rory stayed. But I think we all applauded when she turned down his proposal and chose to focus on her career instead. Now that was the Rory we all knew and loved.
We have waited years to knows if Dean's marriage ever worked out, Jess wrote anymore books, and if Logan actually succeeded in his business endeavors or just ran back to Mitchum. My prediction? Dean's marriage ultimately failed and he's still bumming around Stars Hollow or they're still married but completely unhappy and he cheats more than he's faithful. Jess went on to write more books, his publishing company grew, and he visits Luke on a regular basis. Logan succeeded in his business endeavors, has a seemingly perfect marriage with a Barbie wife, but he drinks and parties more than he's at home.
