The King of Top Tens, David Letterman ended his 33-year
In seven season of Gilmore Girls, Lorelai and Rory Gilmore broke many hearts and got their hearts broken as well. Lorelai got engaged multiple times and married once, and Rory had serious boyfriends, casual dates, and a few relationships that fall somewhere in between. Read on for all of Lorelai and Rory’s potential love interests on Gilmore Girls.
Dean Forester – Rory’s high school sweetheart and her first boyfriend
Played by – Jared Padalecki
Dated – From Season 1 thru Season 3, they dated and then broke up. In the Season 4 finale, they hooked up and dated through Season 5 episode “The Party’s Over.”
Memorable Moment – For their three-month anniversary, he plans a special evening for him and Rory, which ends with him giving Rory a car he fixed up and telling her he loves her for the first time.
Max Medina – Rory’s teacher at Chilton and Lorelai’s fiancé
Played by – Scott Cohen
Dated – From Season 1 off and on, shortly after Rory starts at Chilton, through the beginning of Season 2 when Lorelai runs off the weekend of the wedding.
Memorable Moment – Max proposes to Lorelei in a grand fashion and sends her a thousand yellow daisies.
Christopher Hayden – Rory’s dad and Lorelai’s high school sweetheart
Played by – David Sutcliffe
Dated – Lorelai and Christopher wanted to be together, but they couldn’t get their timing right. It seemed like something could really happen in Season 2, but in the Season 2 finale, it was revealed that his girlfriend Sherry is pregnant. He chose to stay with Sherry. Eventually, he and Sherry break up but share custody of their daughter Gigi. At the end of Season 6, Lorelai and Luke break up, and she sleeps with Christopher. They date in Season 7, and on a trip to France, they spontaneously decide to get married. Their marriage does not last, though, and they split up later on in the season.
Memorable Moment – Before Sherry’s pregnancy is revealed, Lorelai and Christopher have a very sweet, romantic time at the inn leading up to Sookie’s wedding.
Rune – Jackson’s perpetually crabby cousin
Played by – Max Perlich
Dated – One horrifying double-date with Sookie and Jackson, possibly the worst double-date in history, until the incident with Dean, Luke, and a Bop-It.
Memorable Moment – The ill-fated double-date gets off to a terrible start when Rune complains loudly about Lorelai’s height and her “big ears.”
Peyton Sanders – An acquaintance of Richard and Emily Gilmore who meets Lorelai at an auction
Played by – Jon Hamm
Dated – For only one episode. He is so dull that Lorelai immediately regrets agreeing to a date.
Memorable Moment – They adorably bid on a last glass of wine at the auction bar.
Alex Lesman – Friend of Sookie’s former co-worker and Lorelai’s boyfriend
Played by – Billy Burke
Dated – From Season 3 episode “I Solemnly Swear” when they meet at an adult education seminar through “Swan Song” when they go to New York City with Sookie and Jackson.
Memorable Moment – After seeing a musical during their excursion to New York City, everyone tries awkwardly to find something nice to say about the show before all happily agreeing that it was awful.
Jess Mariano – Luke’s nephew and Rory’s second boyfriend
Played by – Milo Ventimiglia
Dated – From the middle of Season 3 until he disappears at the end to visit his father out in California. He shows up again in Season 4’s penultimate episode “Last Week Fights, This Week Tights” and asks Rory to run away with him. He shows up again a few times before the end of the show and has become a successful published author.
Memorable Moment – Rory runs into Jess after she drops out of Yale, and he tells her that she is making a huge mistake with both leaving Yale and dating Logan.
Jason “Digger” Stiles – Richard Gilmore’s business partner and childhood acquaintance of Lorelai
Played by – Chris Eigeman
Dated – From near the beginning of Season 4 until the end of Season 4 when Lorelai decides not to reconcile with Jason and kisses Luke.
Memorable Moment – When Lorelai has a sleepover and realizes that he really has her dream apartment with a few caveats, mainly Jason’s overly trained dog Cyrus.
Marty – Friend of Rory at Yale
Played by – Wayne Wilcox
Dated – Never, but Marty always had an unrequited crush on Rory which turns creepy in the show’s final season.
Memorable Moment – The first time Rory and Marty meet, Marty is naked in the hallway, and he can’t find his way home.
Trevor – Classmate of Rory at Yale and Rory’s experiment in casual dating
Played by – David Clayton Rogers
Dated – Only one awkward date which included conversation about dinner mints with residual urine on them and uncomfortable drafts.
Memorable Moment – Trevor catches Rory’s attention by agreeing with her during a class debate.
Logan Huntzberger – Classmate of Rory at Yale and son of newspaper giant Mitchum Huntzberger
Played by – Matt Czuchry
Dated – Midway through Season 5 after Rory and Dean break up, Rory and Logan start dating non-exclusively, which distresses Rory more than she would like to admit. He doesn’t agree to date exclusively until Rory threatens to break up with him, and they date all through Rory dropping out of Yale and getting back into Yale. They also break up briefly when she finds out at Logan’s sister’s wedding that he slept with the whole bridal party. They finally break up in Season 7 at Rory’s graduation from Yale when he proposes and she says no.
Memorable Moment – There was the time he encouraged Rory to steal a boat, and the time he bought her forgiveness by hiring the coffee cart for her personal use. Also, there were all the times he called her “kiddo” and that one time when he was totally horrible and mean to Rory in front of a friend she hadn’t seen in years. Let’s face it, Logan Huntzberger was almost always the worst. Just check out their very first meeting.
Luke Danes – Owner of Luke’s Diner
Played by – Scott Patterson
Dated – From the beginning of Season 5 through the finale of Season 6. At the end of Season 5, Lorelai proposes to Luke, and he accepts. They break up in the finale of Season 6 when Luke refuses to elope with Lorelai.
Memorable Moment – During their first date, Luke shows Lorelai a horoscope that she gave to him on the very first day they met.
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