Random Love Interests on Gilmore Girls (13 items)

• (#1) Luke Danes

  

  The original lumbersexual, Luke was the grouchy diner owner who pined for Lorelai for years before they finally got together.

  Pros: He made her an ice rink, a chuppah, AND coffee every morning, he gave her money for the Dragonfly Inn, he was the closest thing Rory had to a father figure, he was always there for both of them.

  Cons: He let their relationship fall apart.
• (#2) Dave Rygalski

  

  
  He was in a band with Lane and he was her first kiss. AND he read the whole Bible just to impress Mrs. Kim. Seth Cohen, who?

  Pros: He's a musician who loved music as much as Lane, and he was willing to pretend to be in a Christian band so Mrs. Kim would like him.

  Cons: He left Stars Hollow (to go to The O.C.). 
• (#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.
• (#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.
• (#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."
• (#6) Doyle McMaster

  
  

  
  Paris's paramour was just as quirky as she was. Despite their ups and downs, they made it work.

  Pros: He genuinely loved and supported Paris and he was a good friend to Rory.

  Cons: As Paris and Rory's editor, he was less endearing than annoying.
• (#7) Zack Van Gerbig

  

  Zack: The passionate songwriter and Lane's clueless, yet well-meaning boyfriend.

  Pros: He always tried to do right by Lane and her mom, he was just as passionate about music as Lane, he was a responsible dad and husband.

  Cons: He started out as kind of a womanizer, and he needed to be told what to do more often than not.
• (#8) Max Medina

  

  He was Rory's professor at Chilton and Lorelai's first fiancé.

  Pros: He seems like an all-around good guy, he proposed with a thousand yellow daisies, and he got along with Rory.

  Cons: They were never quite the right fit, they had no chemistry, and he could never really compete with Luke.
  
• (#9) Dean Forester

  

  Ah, young love. Dean was the cute guy at Stars Hollow High School who eventually became Rory's first boyfriend.

  Pros: He was a perfect gentleman, he built her a car for their anniversary, he was Lorelai-approved.

  Cons: He was kind of boring (especially when compared with bad boy Jess), and he later cheated on his wife with Rory.
• 

  (#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.
• 

  (#11) Marty

  

  Rory found him lying naked in the hall of her dorm and he lived in the friend zone forever after.

  Pros: He's a good, down to earth guy who was always kind to Rory.

  Cons: He ended up with Rory's college friend, Lucy, and lied about knowing Rory.
• (#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. 

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