Random Love Interests on Gilmore Girls (13 items)

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  (#10) Tristan Dugrey

  

  The Chilton bad boy who harbored a secret crush on Rory.

  Pros: Um, he looked good in the Chilton uniform?

  Cons: He constantly teased Rory and dubbed her "Mary," poking fun at her good girl persona, and he came on to her while she was with Dean.
• 

  (#4) Jackson Belleville

  

  Sookie's produce-guy-turned-husband may have been the sweetest man on the show.

  Pros: He was a devoted husband, father, and produce man, he was a loyal friend to Lorelai and Rory, he slept with his vegetables to protect his crop.

  Cons: He never got the vasectomy Sookie wanted him to get... so she ended up pregnant.
• 

  (#12) Christopher Hayden

  

  Lorelai's high school boyfriend was not exactly the most present person in the lives of his daughter and baby mama.

  Pros: He's Rory's father, he's always loved Lorelai, and he tried to make it right when he finally had the means to support the family.

  Cons: He was never really there for the girls, he tried to break up Lorelai and Luke at one point, he left Lorelai when his girlfriend got pregnant (that's no easy situation, but you don't just up and leave like that), and he was a cool high school boyfriend but never really grew out of that high school mentality. 
• 

  (#13) Jason “Digger” Stiles

  

  Lorelai's short-lived romance with Digger ended with him asking her to choose him over her family, so needless to say, it didn't end well. 

  Pros: He and Lorelai had some history (summer camp) and he seemed to make her happy... for a little while anyway.

  Cons: Literally everything about him was wrong for her, he made her sleep in a separate room because he was a light sleeper, he didn't have a great relationship with his family, and he eventually ruined his relationship with Lorelai's parents. 
• 

  (#5) Logan Huntzberger

  

  Rory's college sweetheart was sometimes a great foil, but other times an entitled jerk. He did propose in the end, but the ever-ambitious Rory rejected him.

  Pros: He's adventurous, charismatic, and witty, and he genuinely cared for Rory and was there for her (most of the time).

  Cons: He drank too much, he was irresponsible and cocky, and he slept with other girls while they were "on a break."
• 

  (#3) Jess Mariano

  

  The bad boy with a brain swept Rory off her feet.

  Pros: He loved books as much as Rory, he set her straight when she decided to take time off from Yale, and he could be considerate and caring.

  Cons: He had commitment issues, he was irresponsible and disrespectful at times, and he up and left Stars Hollow without saying goodbye.

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