With Gilmore Girls ending its run in 2007, the already popular show gained viewers from the next generation when it moved to Netflix in 2014. With the increased popularity of the show, more polarizing opinions have formed than ever before. One controversial topic is the iconic discussion of who Rory Gilmore’s best boyfriend was in the series. 

Rory Gilmore had her fair share of boyfriends throughout the show’s run. As she moves from Stars Hollow High School to Chilton High School and finally, to Yale University. 

Starting with Rory’s first boyfriend, Dean Forester, or the so-called perfect boyfriend. In the beginning, viewers love him and how he and Rory met. People expected them to be the high school sweethearts, but what would a show be without a plot twist? 

Towards the end of season two Dean’s true personality starts to show with character traits like jealousy, manipulation, and control. Yes, I understand he’s a teenage boyfriend, but he made it very difficult for Rory to be open without him yelling at her. And much later in the show, let’s not forget about how he cheated on his wife with Rory and then got mad at his wife. I rate Dean Forester a solid 3/10. 

While Rory was attending Chilton, she met Tristan Dugray. Yes, Rory and Tristan never officially dated, but he was a crucial part of her beginning time at Chilton. Tristan was the original bad-boy character. The only problem was he hid his huge crush on Rory with insults and nicknames. Rory deserves better than someone who constantly calls everything she does weird. I rate Tristan Dugray a 5/10. 

Next, we have Jess Marino, Rory’s most iconic boyfriend. Jess brought out a different side in Rory that the audience had never seen. During the time they dated, Jess was supportive of Rory and never put her dreams down. They could talk to each other about their favorite books and movies. Overall, Rory and Jess could relate to each other on a different level. However, some issues happened during their relationship like when Jess left to go to California to start a new life, but didn’t tell Rory. Jess didn’t care to tell anyone and completely ignored him and Rory’s relationship. In the end, it all worked out as Jess went his own way, matured, and then came back and was still so proud of Rory and fully in love with her. The sad thing is, that Rory had moved on with her life and met a new person. Jess was the definition of the right person at the wrong time. I rate Jess Marino an 8/10. 

The next boyfriend is someone everyone thought Rory was going to marry until she declined his proposal. Rory met Logan Huntzberger during her time at Yale University. Logan taught Rory how to loosen up a little and live her life to the fullest. 

 When Rory needed a home, he opened his doors to her. Yes, Logan could be a little arrogant but he always had Rory’s back and never left her side no matter what. 

In season five episode seven, “I Jump You Jump Jack.” Logan taught Rory the YOLO lifestyle and pulled out a different side of Rory. Logan was her healthiest relationship and I rate Logan Huntzberger a 9/10. 

Throughout Rory Gilmore’s life, she had many boyfriends—all with different personalities, backgrounds, and a different effect on her. After watching the Gilmore Girls series, I’ve established that Rory and Dean were toxic, Rory and Tristan could have been so cute, Rory and Jess were soulmates, and she and Logan would’ve lasted forever.