1. Jess
Jess made some (read: a lot) of bad decisions. He antoganized Dean, Rory's then boyfriend, which led to a very humiliating public breakup. When he finally got the chance to be with her, he screwed it up by trying to have sex with her and then getting into a fight with Dean about it. He skipped town, and only when he heard Rory was moving on did he come and confess his feeling for her. And then (yep, you guessed it) he left again, only to return for his mother's wedding and an improptu visit to Rory's dorm at Yale. He then asked her to leave school, throw her life away, and come with him to New York. True, her response probably left him heartbroken, but he kind of deserved it. And it isn't just his decisions that are lacking in sensitivity. His general attitude towards the world at large needs some serious work. He tends to be moody, grumpy, and unnaproachable, which is only enhanced by his whole, "I am a bad boy, woe me" look. However, Jess does have some good points. His appearance, for one, far outweighs any of Rory's other boyfriends. His height matches her's much better than Dean's, and he manages to wear the leather jacket without making it look too forced. Jess is also incredibly smart. He matches Rory intellectually and manages to challenge her in ways that Dean never could. Eventually, he even wrote a book! Jess really could have been the perfect partner for Rory... If he had gotten himself together when he had the chance.
2. Dean
Oh, Dean. Honestly, I really pity him. He was always really jealous of both Tristan and Jess, which led to many fights and disagreements. Rory did treat him badly, but instead of slowly healing and moving on, he got married to Lindsey, a sweet blonde house wife, who also didn't deserve what she had coming. But let's go back a couple seasons to the first ever episode of Gilmore Girls, when Dean first came into the picture. From the beginning, he was always sweet and supportive. Their relationship lasted 2 years, while Jess' in comparison ended after barely 5 episodes. However, Dean was always a little more ready than Rory for a serious relationship. After dinner for their 3 month anniversary, Dean took Rory out to a car, which he had been BUILDING HIMSELF. That takes serious commitment, something which Jess seriously lacked. Unfortunately, their relationship kind of failed after that. Dean told Rory he loved her, and when she hesitated for a split second, he broke up with her. Rory was heartbroken, and even worse, he was barely civil to her after the breakup. After they got back together, things turned weird. Dean changed from the sweet boy we had learned to love to a jealous teenager who rarely let Rory out of his sight. He insisted accompanying Rory to all her rehearsals for the school play and became protective to the point of being ridiculous. I think, by the end, we were quite relieved when Jess came along. But Dean wasn't done there. After being married (at 19, I might add) he dragged Rory into his relationship and made her "the other woman" by having sex with her. Rory, being the nice, stand up person that she is, asked what happened the Lindsey, and Dean lied, saying that they had broken up. This put Rory in a horrible position. However, Dean never did anything to hurt Rory directly. Moving on to Dean's appearance: to be frank, it wasn't the best. He was always wore baggy clothes: his leather jacket fit him terribly, unlike Jess'. He grew out his bangs into curtains that almost covered his eyes, and grew a sort-of moustache. However, he was handsome in a tall, lanky sort of way.
So, who is it? Show your opinion in the poll below!