Besides an on-again, off-again relationship with Rory's father,
Over seven seasons, Lorelai had some very serious romances, but she actually only dated seven guys, which is pretty surprising for the queen of single ladies in Stars Hollow. That being said we ranked all of her BFs from number seven down to the perfect man. Can you guess who it is? 7.
While she's excited to be engaged to Luke, the introduction of April makes their lives tricky and Lorelai sees the dream of being with Luke forever slipping away. At the end of season 6, Lorelai and Christopher sleep together and begin their relationship again.
Lorelai is forced to tell Luke that she slept with Christopher last night. Luke says nothing but drives away. At first, Lorelai and Luke remain somewhat detached but supportive after their break up.
Season 4: Rory Loses Her Virginity To Dean
Dean and Rory don't actually spend a lot of time around one another during season 4 of Gilmore Girls. Rory is busy trying to find her footing in college and Dean is navigating married life.
Lorelai did cheat on Luke because she said marry me now or never she didn't say the relationship was over. And Lorelai said several times Luke didn't want to marry her and Luke never said that he never wanted to marry her once in that entire series.
They go through everything together across the seven seasons and miniseries revival, and they have many incredibly romantic quotes that show why they were soulmates. Fans aren't the only ones who can tell from the very beginning of the show that Luke and Lorelai are meant to be together.
Lorelai Slept With Christopher When She And Luke Broke Up
The first time that happened was at the end of season 1, when Lorelai and Luke seemed to be flirting more than usual, only for her to be distracted by Christopher, who suddenly wanted to nurture his relationship with Rory.
Written In The Stars (S5, Ep 3)
Of course, this is their first date, and the first time they sleep together, which makes it an amazing episode for the couple, but it's also the episode where Lorelai accidentally clues the whole town in and they end up being discussed at the town meeting.
Logan Is Likely the Father of Rory Gilmore's Baby
During the events of A Year in the Life, Rory had been sleeping with Logan for a while.
There was so much wrong in their relationship that some fans labeled the couple toxic. After all, they did break up twice.
Longtime fans of Gilmore Girls will note that historically Rory had three prominent boyfriends during the original run: Jess, Logan, and Dean. But the game of “Best Rory boyfriend” is not a three-man race, so much as it is two men and a very tall baby.
He hands Lorelai a check in her name for $75,000. Instead of waiting just one week to learn Rory's tuition costs, Lorelai promptly gives most of the money back to her parents in repayment of a debt.
Lorelai's Jealousy Over Rory And Her Parents
Rory ended up having a lovely time and enjoyed her grandfather's company. This wasn't something that Lorelai was expecting and she took her jealousy out on Rory. Since Lorelai never had that kind of relationship with her dad, she hated that Rory was getting close to him.
Rory cheated on almost every single one of her boyfriends, except Jess. However, she did cheat on Logan with Jess — unbeknownst to him. During a fight with Logan, Rory went to Jess in Season 6, Episode 18 and kissed him.
By the end of the episode, it hit Lorelai that Christopher was right — she wasn't fully in their marriage. She and Christopher no longer fit in each other's lives and she wasn't over Luke. They agreed to end their marriage and focus on Rory as co-parents instead of as husband and wife.
And even though Luke and Lorelai do get their happy ending — it still bothers me that at the end of the sixth season, she slept with Christopher (David Sutcliffe) and then married him in season 7. Seriously, it has kept me up at night. And here's why. 1.
Dean Forester (played by Jared Padalecki) was Rory's first real crush, and despite the fact that they never officially dated while attending the same school, they were total high school sweethearts. He was the all-around wholesome boy who worked at Doose's Market in Stars Hollow and treated Rory like a total princess.
Luke: Was Always There For Lorelai Without Being Asked
One of the biggest issues Lorelai had with Christopher was how flakey he was. He left her when she was pregnant and he wasn't really helpful when Lorelai was raising Rory by herself.
Luke Danes was, by far, the greatest love interest any character on Gilmore Girls had. From the very first episode, the diner owner was clearly smitten with Lorelai. Lorelai had a few different love interests throughout the course of the series, but Luke was always her best fit.
Jamie's character is brought back when Paris begins to have an affair with a Yale professor, Asher Fleming, and Paris strings Jamie along, even though her heart belongs to Asher. Jamie comes to visit Paris at Yale on his birthday, and Paris breaks up with him, per Rory's advice.
The ultimate Gilmore Girls betrayal happened in the season 5 finale with an unexpected storyline that still feels like a gut-punch. Rory not only stole a yacht and took time off from college, but she betrayed her mother horribly by moving in with Emily and Richard. She always asked her mom for advice and leaned on her.
Rory quickly develops a crush on Richard's replacement TA and feels compelled to confess the attraction to Logan.