Posted by Tisha Mae Eaton @TishaMaeEaton
Verified Creator. I like a little bit of everything. Resident know-it-all of all things Disney
Tisha Mae Eaton

Gilmore Girls was a great show, with witty dialogue and episodes that were funny and heartfelt all at once. There was also a plethora of unforgettable characters, and none divided or united fans of the show more than Rory Gilmore's (Alexis Bledel) boyfriends. Everyone has a favorite boyfriend of Rory's. Dean (Jared Padalecki) was an adorable first boyfriend, though he became less favorable as the seasons went on, and Logan (Matt Czuchry) took her out of her element. But it was Jess (Milo Ventimiglia), in my opinion, who was the best suited for her. He helped her grow, and while he was a bit of a troublemaker, he really cared for her and met her on an intellectual level that he didn't let many people see. With the revival coming soon and in honor of it being Milo Ventimiglia's birthday, here is a look at some of his best moments on screen.

1.'Jess.... Ma'am.'

Jess is caught talking to Lane by her overprotective mother, who immediately runs over to demand who he is. Jess, being one of the toughest characters on the show, is nonetheless intimidated by the fierce little woman and immediately defers to her. Just one of those silly little moments that is overlooked but so good.

2. Outbidding Dean On Rory's Basket

While it was kind of a jerk move, this was one of those moments that was genuinely funny. Being competitive and wanting to win her back, Jess outbid Dean, Rory's current boyfriend, for her lunch basket and Jess and Rory have a picnic on a bridge by the lake. The whole episode was sweet, and was also when Jackson and Sookie got engaged so, you know, added bonus.

3. 'I Thought This Was The Uniform.'

Jess was always taking little jabs at Luke, his caretaker. This one found him teasing Luke about his constant plaid shirt and backward baseball cap. It was fun and those who loved Lorelai's little comments about Luke's rarely-changing attire appreciated this moment.

4. 'Welcome Home.'

After having disappeared for some episodes because of the car accident he and Rory got into, it was very satisfying to see him finally return in the Season 2 finale for Sookie's wedding to get a kiss from Rory and a proper welcome home.

5. When He Got Into A Fight With A Swan

Am I the only one who wishes that we could have seen this? At some point, Jess got attacked by a swan, and while I know it led to some tension between him and Rory when he was too embarrassed and lied to her about it, his discussion about it with Luke was funny. Plus, the whole mystery of what happened had viewers (ok, maybe just me) on the edge of our seats for the entire episode.

6. 'You Googled!'

After Rory decided to go to Yale in Season 3, one of the sweetest little moments between her and Jess was when he told her that he Google mapped the distance from Stars Hollow to Yale for visits. At 17-18 is there anything more romantic than thinking you'll be together forever? I think not.

7. Walking His Mom Down The Aisle

Even though Jess hadn't wanted to go to his mom's wedding due to her having been married so many times before, he showed up anyway to support and make her happy, walking her down the aisle to TJ. He put aside his own feelings and did something that was honestly very selfless, even if it seems as though it were just a little thing.

8. When He Finally Told Rory That He Loved Her

While it was a little too late by the time Jess finally was honest and confessed his feelings to Rory, it was sweet and kind of amazing to finally see it happen. She was the one person who always believed in him outside of Luke, and to finally see him say those three little words was so satisfying (and watching her run to him was great too).

9. Finding Out That He Had Published A Book

In Season 6, Jess reappears in Rory's life to tell her that he'd written a novel and that Rory is who helped him to accomplish it without realizing it, which is so romantic! He had clearly grown up since the last time that we saw him (all the way back in Season 4), and to see him so accomplished in his second-to-last appearance was a stark contrast to when he first showed up in Stars Hollow.

10. When He Convinced Rory To Go Back To Yale

Also in Season 6, Rory seemed to have lost herself before Jess reappeared, having a falling out with Lorelai, stealing a yacht, partying and dropping out of Yale. But after his return Rory decided to go back to school and finish, eventually becoming a journalist. Jess reminded her that she was better than the way she was acting, and that brought her back to reality, which is the greatest thing he ever did for Rory and something for which he should be thanked.

Jess was a funny, sarcastic, difficult and intelligent character, and I cannot wait to see what he has been up to since we last saw him. Make sure to catch up on the show by watching it on Netflix, and keep an eye out for more news on the revival!

Poll

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