Sorry "Gilmore Girls" fans, but there will never be a Jess and Rory.
Most "Gilmore Girls" fans will probably agree that Jess Mariano is the most suited boyfriend for Rory. They match each other intellectually. They share the same interests and both are voracious readers. However, being together was never in the cards.
First, because of the marriage of Luke and Lorelei, Jess and Rory are technically cousins-in-law. Meaning, they are family now. Just imagining Luke and Lorelei and Rory and Jess as married couples gives off an immoral vibe. It is like twins marrying twins
Second reason is that they are both writers. While we thought that Jess will lead a Jack Kerouac's "On The Road"-kind of life, he ended being a successful writer. However, sometimes two people sharing the same profession do not always match. Think Sylvia Plath and Ted Hughes. There will be a constant power struggle like who is more successful or whose books sell more.
Lastly, if rumors proved to be true that a "Gilmore Girls" spin off will be in the works. Milo Ventimiglia may not be able to participate since he is busy being the husband of Mandy Moore and the father of the Big Three in NBC series "This Is Us".
"Gilmore Girls" creator Amy Sherman-Palladino got the whole gang together for a special reunion, but the screenwriter pulled a major cliffhanger just when we thought that we will get our happy ending for the "Gilmore Girls".
The last scene of the Gilmore Girls revival closed in a cliffhanger revealing Rory is pregnant. While many fans are hoping that Jess is the father , it is implied that baby is Logan's. However, Logan is engaged to a French heiress, Odette, and he intends to marry her because of his family obligations.