It is almost impossible to watch Gilmore Girls and not have an opinion on Rory's three major boyfriends. Team Dean, Team Jess, and Team Logan are all passionate about their pick of the guy most worthy of the awesome Rory Gilmore, but I want to put the big picture to the side for the moment and focus on which one of Rory's boyfriends was the most romantic. I am taking my own Dean, Jess, and Logan feelings out of the equation and instead focusing on the big gestures each guy used to woo Rory.
Romance is a huge part of the Gilmore Girls world. When you exist in a universe where a man will send you 1,000 yellow daisies or build an ice skating rink in your front yard to get you back together with snow, you really have to go big or face not winning over the heart of a Gilmore woman. While Lorelai's boyfriends were all epic in the grand gesture department, Rory's partners were no slackers either.
Granted, romantic gestures are not the best indicator of what will make for a long-lasting relationship, but building someone a car from scratch will almost always lead to swooning. It's time for Dean, Jess, and Logan's most romantic moments to be compared so the world can finally know which one of Rory's boyfriends was the truest romantic.
When it comes to first boyfriends, Dean was a serious catch. Not many 16-year-old boys would make their girlfriend a hand-crafted bracelet, never mind build them a car. These were Dean's two big grand romantic gestures, but they were by no means the only times he got super romantic. Dean is also the guy who volunteered to watch Rory browse for books, the one who picked her up from a crappy date long after they broke up, and the one who learned to dance for her, even though he was nervous about it.
Dean was big on romance throughout his relationship with Rory, and his style was as earthy as he was. His gestures were grounded in things he could make with his hands and the emotional support he could offer. It was never about flash with Dean; it was about substance.
Jess' romantic gestures were uniquely Jess-esque. For instance, the first major gesture he made and the one that piqued Rory's interest was when he stole her copy of Howl and filled it with annotations. He followed this gesture up with destroying the best snowman so Rory and Lorelai's Bjork snowperson would win the competition. Jess continued the bad boy brand of romance by ending Rory's tenure as the face of censorship in Stars Hollow by switching out wholesome movies for less than wholesome movies at the video shop, bringing down the short-lived Rory Curtain.
It wasn't all debauchery with Jess, though. The boy could do good, old-fashioned romance as well. He bought Rory's picnic basket of grossness, he came back to Stars Hollow for her, and he declared his love for her in an impassioned plea for the two of them to runaway together. Of course, his best romantic moment will forever be waking Rory up and reminding of her drive and ambition after she dropped out of Yale. Also, let the world never forget he turned off the sprinklers for her and then turned them back on again.
Ah, the illustrious Mr. Huntzberger — if ever there was a go big or go home romantic gesture kind of guy, it was Logan. He was the man who taught Rory about the in omnia paratus way of life. He talked her into jumping off a tower with him, and he gave her an intricate Twilight Zone-themed puzzle to solve, which she called the most romantic thing anyone had ever done for her, although after talking to Logan the gesture itself seemed a little emptier than he intended.
Logan's best moments of romance were the simple ones. When he stayed up all night to help Rory get the Yale Daily News out on time, hearts everywhere melted. And they melted again when he confessed that he preferred Rory over London no matter what Samuel Johnson said. Logan was also the man who was wise enough to ask Lorelai for permission to ask Rory to marry him, rather than her father.
While some of Logan's biggest gestures never felt quite right, the moments when he allowed himself to be vulnerable proved to be the most romantic moments of them all.
And The Winner Is...
Dean's brand of romance was sweet and down to earth while Logan's tended to be grand and over the top, but Jess Mariano found that Rory-specific romance sweet spot. He read books for her, he destroyed snowmen, and he restored her faith in herself. All three guys had big hearts, but Jess was the king of romantic gestures both big and small.