If there’s anything “Gilmore Girls” fans love, it’s debating Rory’s best boyfriend. With the revival taking place 10 years since we last left Stars Hollow, it’s likely Rory will have finally chosen between her three guys. Weekend makes a case for each.
No matter how strongly many “Gilmore Girls” fans may feel about Jess and Logan — and, by comparison, how little they care for Dean — there’s no denying that Dean Forester was Rory’s best boyfriend.
All Dean ever wanted was to love Rory, and he did it well. The boy built her a car, told her he loved her, and in true Rory fashion, she broke up with him. They promptly got back together after she realized her mistake, resulting in one of Rory’s best moments of the entire show — “I love you, you idiot!”
Rory and Dean have always been on the same wavelength. Jess avoided committing to Rory for far too long, allowing her to pine after his emotionally unavailable broodiness. Logan prioritized his own relationship timeline, continually pushing Rory for too much, too fast.
Dean is the only person who’s hit relationship milestones at more or less the same time as Rory — or if she hasn’t been ready, he’s been willing to wait.
Admittedly, being so in-sync hasn’t always worked. When neither party in a relationship is ready for another long-term relationship, it’s pretty much doomed to fail.
We all know the catastrophe that was their third attempt together, but Rory and Dean share equal blame in that. Rory has always had a bad habit of playing with Dean’s feelings, and he’s never quite been able to extinguish the torch he carries for her, even when he’s already committed to another woman.
Timing is everything for this couple. Maybe 10 years later, now that both of them have had a chance to grow up and move on, they can finally make it work for good. Rory was always the less emotionally mature one in their relationship, although Dean clearly wasn’t ready for the marriage that he forced himself into.
A decade is a long time, and if anything is for sure, it’s that Dean is still in love with Rory. We know that he’s important to her — he was her first real boyfriend, her first real love. If this revival is truly going to bring everything around full circle, maybe it’s time these longtime lovers finally got another shot.
On the surface, Jess Mariano has a lot working against him. Rory’s second boyfriend was a controversial choice from day one. He stole, fought, vandalized and made an enemy of just about everyone in Stars Hollow. He won Rory away from loyal, lovable Dean, accidentally broke her wrist in a car crash, dropped out of school and left Rory without warning.
Jess was certainly a troubled teenager, but his life turned around for the better as soon as he met and fell in love with Rory. They had an insane amount of chemistry, especially compared to her lukewarm relationship with Dean, and their time together seemed like the first time that Rory really knew what — and who — she wanted.
Jess and Rory had more in common than any of Rory’s other friends. No one loves books or punk music more than the two of them, and Jess was the only true intellectual match that Rory ever really found.
That said, it’s when they were at odds with each other that Jess and Rory’s real potential came to light. Rory challenged Jess to be a better person, and he was at his most likable when he felt he had to do his best to please her.
Later in the show, when Rory dropped out of Yale, was dating Logan, stopped talking to her mother and moved in with her grandparents, only Jess was able to snap her out of it. Rory had reached Jess when no one else could. He proved he’s able to return the favor.
Where Rory’s other boyfriends tended to get worse as the show went along, Jess only matured and improved.
Ten years later, who knows what Jess will be up to? Last we saw him, he was a published author and owned a bookstore in the city. We know he’ll end up in Stars Hollow at some point in the revival, but it’s anyone’s guess as to why.
Anyone who has watched “Gilmore Girls” knows that Rory is far from perfect — she can be immature, naïve and selfish. Likewise, Jess can be rude, short-tempered and altogether hard to take. But together, they’re at their best. Rory is a better person with Jess, and vice versa.
We all know Dean was the perfect first boyfriend and Jess was the perfect bad boy, but Logan is the winning combination of spicy bad boy and perfect fit for Rory.
Logan came into the picture as Rory was just starting to get settled into Yale University, with high hopes for her journalism future. The prospect of the highly unrated relationship with Marty, also known as naked guy, always seemed like an interesting contender.
However, that never became a reality because once Logan graced the same halls of Yale falling into the same scenes as Rory, there was no chance for poor naked guy — regardless of the leftovers he would bring to her dorm room after his catering gigs.
Logan comes from a good family full of connections, and although this may seem shallow, it is important to know. Rory is extremely low-maintenance, and we love her for that, but she deserves the best life possible, and Logan can make that happen out of his unconditional love for her.
There are the drawbacks to Logan, including his immaturity in serious situations, his ability to be a “butt face miscreant” when he isn’t thinking straight, and we can never forget that time he allowed Rory in a lacking mental state to steal a yacht.
Regardless, Logan’s wit, intellect and ability to make Rory smile makes him the perfect fit for her.
Logan not only pushed Rory to be the best version of herself, Rory got to accept all aspects of her life. This includes both her small town Stars Hollow life and her posh Hartford grandparents’ world.
Although his proposal may have been premature, Logan’s intentions were always genuine. He wanted the best for Rory, and he had the ability to make her happy in ways Rory didn’t know existed.
This blonde-haired beauty can win the hearts of so many girls, but we all know the only girl that can win his is Rory.
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