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The cult favorite show, Gilmore Girls, is known for its mature and layered take on mother-daughter relationships. As a show from the aughts, this nuanced portrayal was rare and therefore beloved.
But even though the central focus was on the ‘Gilmore Girls’, the series also branched to portray teen life, single parenthood, womanhood through generations, and their sometimes wholesome and often complicated relationships with men.
Set in the small, fictional town of Stars Hollow, the backdrop is cozy, and for those who have forgotten who the duo end up with—in the original series and the Netflix revival—let it be known that while Lorelai ends up with Luke, Rory doesn’t end up with anyone.
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More details on the dating history of Lorelai Gilmore in Gilmore Girls
Starting with Lorelai, the strong-headed single mom has dated a few men during the course of the show. Her first boyfriend is Rory’s father Christopher Hayden, who Lorelai breaks up with, to single-handedly raise Rory. But he keeps coming back, once during season 2, and once during season 7—when they end up marrying. But it soon ends in divorce.
Apart from Christopher, Lorelai dates Max, with whom she has an on-off relationship throughout season 1. Eventually, Max proposes to Lorelai at the end of the season, but at the start of the next season, Lorelai runs away and practically ends her relationship.
She then briefly dates Rune, Paul, Peyton, and Alex. And has a bit of a complicated run with Jason that causes a break-up due to business and family misunderstandings.
Ultimately, fan-favorite Luke is an ever-constant presence in Lorelai’s life and even grows close to Rory. From the first season of Gilmore Girls itself, a bond is shown between the two, but it is only in season 5, that they start dating. Yet, their first engagement doesn’t last long when Lorelai gets to know that Luke has a daughter which complicates their relationship.
It is only in the spin-off, A Year in the Life, that Lorelai takes the plunge to marry Luke in the last episode after living together for nine years.
The love life of Rory Gilmore in Gilmore Girls
Rory, on the other hand, has three major men in her life—Dean, Logan, and Jess. And also had a few brief encounters with characters like Sean, Paul, Robert, and Tristan.
To begin with, Rory and Dean start off on a good note in season 1, but soon, Dean’s obsessive side creates trouble when Jess comes into the picture. He also does some questionable things that prompt the viewer to forget about him quickly.
Jess and Rory’s relationship also has its difficulties as Jess is portrayed as the emotionally unavailable guy. He also creates rifts between Rory and Dean when they are dating and ultimately lies and runs away without informing Rory while the two are still a couple. Yet, in the later seasons of Gilmore Girls, the viewer meets a more mature Jess, but by then, Rory has moved on to Logan.
Finally, with Logan, Rory feels more connected and the two are intellectually compatible. Yet, when they start dating in season 5, Logan doesn’t want to commit initially. And even he has his faults, like when he wants Rory to leave her place for him. Ultimately, he does propose to her in season 7, but Rory turns him down.
In A Year in the Life, we see Rory and Logan having a sexual relationship with each other, even when they both have other partners. And when Rory ends up pregnant, she decides to raise her child single-handedly —just like her mother—and ends the show being single.
Relationships are the cornerstone of Gilmore Girls and viewers are welcome to go down memory lane and refresh their favorite characters’ romantic moments by going through this list.
