Gilmore Girls: Lorelai’s Boyfriends Ranked

On Gilmore Girls, Lorelai really didn’t date that much. She had a few casual boyfriends and a couple of serious ones but, other than that, it really seemed that she spent a lot of her time on the series being single. Now that we’ve seen the revival and we finally got the ending that we all wanted for Lorelai and Luke, we’re ranking Lorelai’s boyfriends on the show from worst to best!

6. Peyton Sanders

Lorelai only went on one date with Peyton Sanders, so he wasn’t exactly a boyfriend; however, she did have to jump through hoops to get that date after meeting him at an auction. She wound up getting his name and number from her mom Emily, which was pretty much the first sign that this date might not be worth pursuing. After the date, Lorelai complained to Rory that he had no personality and no sense of humor and the only reason he remained in the storyline was because her parents got upset with her for rejecting him.

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5. Alex Lesman

Lorelai and Alex were never that serious. In fact, their relationship seemed like something Lorelai did just to pass the time while she waited for Luke to make a move. Their relationship also wasn’t very memorable. The only slightly memorable part was when she prepared for their fishing trip by having Luke teach her how to fish. This had us thinking…why isn’t she just dating Luke?

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4. Jason “Digger” Stiles

Lorelai’s relationship with Jason Stiles had disaster written all over it. Their parents were enemies; Jason was in business with her father; and Jason didn’t like to share a bedroom during their sleepovers, so she had to sleep in his guestroom. Even though Jason and Lorelai shared a similar sense of humor and they’re both a little off center, their relationship ended in disaster when her father screwed him over by going back into business with his conniving father and Jason threatened to sue Richard.

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3. Christopher Hayden

Lorelai and Christopher had a lot of history but, unfortunately, a lot of that history wasn’t good. Whenever he would come back into Lorelai or Rory’s life, he would end up flaking out on them. Lorelai and Christopher had that one opportunity in season two when they could have been together, but he ended up leaving Lorelai because his ex Sherry was pregnant. Even though Lorelai and Christopher did end up getting married in season 7 (which didn’t make a lot of sense), their brief union more or less proved that she always belonged with Luke.

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2. Max Maedina

Max Medina was super nice, but he was also really bland. Even though he proposed to Lorelai and they were planning to get married, it all fell apart when she realized that she didn’t love him the way he loved her. After their breakup, they ended up seeing each other again when he came back to Chilton after teaching a course at Stanford. Lorelai wasn’t able to just stay away from him – until he explicitly told her to. Still, he was really sweet. He just wasn’t the guy for Lorelai.

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1. Luke Danes

It was pretty obvious from the first episode of Gilmore Girls that Lorelai belonged with Luke. While all of her other boyfriends were lacking, Luke was the one who was always there for her. When they did finally get together, it was obvious that he had been pining for her since they met years earlier. Luke and Lorelai did have their problems though – one of them being her parents and the other being his hesitations after he found out that he had a daughter. In the revival, they finally get their happily ever after, which is what fans have been waiting for since the first season.