All of Lorelai Gilmore’s Boyfriends, Ranked—Who Is Your Favorite?

When it comes to Gilmore Girls fans, “passionate” isn’t a strong enough word. From 2000 to 2007, Lorelai felt like a friend, Rory felt like our little sis, Sookie was our confidante, Luke was the object of our affections, and overall, Stars Hollow felt a little bit like home. With that in mind, every time our girl Lorelai had a new love interest in her life, we felt personally invested! Was he going to match her energy? Her sense of humor? Her spunk? While there were certainly a few that didn’t get our stamp of approval (ahem, Rune), there were definitely a couple of goodies! Here, take a look at Lorelai’s boyfriends, ranked. Who is your favorite?

7. Christopher Hayden

It’s safe to say that Lorelai and Christopher had a history that went far beyond any of the other love interests that made their way in and out of her life. After all, he’s the father of Rory! In spite of this and much to the chagrin of the Christopher supporters out there, he simply wasn’t the one. His unreliable nature and ability to string both Lorelai and Rory along time after time made his presence in the show all-too-frustrating—proving that some things are better left in the past. 

6. Peyton Sanders

Though Peyton was merely a blip in the world of Lorelai’s love life, he makes this list solely for the fact that he was played by none other than Jon Hamm! As was most often the case, Lorelai’s forays into the world of her parents very rarely worked out in her favor, and Peyton was no exception. 

5. Paul

Another blip in Lorelai’s love life was Paul, a man she met while attending business school. Although a short-lived fling, his importance as her first romantic endeavor post-Max Medina made him an important one in her journey. 

4. Alex

Alex was brought to life by the hunky Billy Burke, and the chemistry he and Lorelai shared was something we loved seeing. They shared common interests and seemed to really hit it off, but fans were sad to see it eventually fizzle out. Oh, what could have been!

3. Jason (Digger) Stiles

To this day, many fans still stand behind Jason “Digger” Stiles as being a great match for Lorelai. He matched her sense of humor, the duo had great chemistry and they both came from the same world of privilege while maintaining similar outlooks on it. Things eventually went south for the two, but the Jason sympathizers out there still stand behind him!

2. Max Medina

Max was one of Lorelai’s most serious partners, the couple meeting at Rory’s school as he was a teacher there. He proved to be reliable, sensible, mature and committed, but ultimately, Lorelai wasn’t ready for the type of commitment he was looking for. 

1. Luke Danes

This one shouldn’t come as a surprise to anyone, as any true Gilmore Girls fan knows Luke and Lorelai were endgame from the start. The lovable grump always knew Lorelai’s heart and was there for her and Rory through it all. We all wish we had a Luke in our lives. 

Looking for more entertainment stories? Click through below!

I Got To Ride on Taylor Sheridan’s ‘The Road’ Tour Bus With Contestants—and You Can Too!

Gloria Estefan, 68, Shares the 7 Life Lessons That Keep Her Joyful and Creative (EXCLUSIVE)

Martha Stewart Dishes on Gardening’s Benefits and the One Flower She’d Never Plant