10 Most Romantic ‘Gilmore Girls’ Episodes, Ranked
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The month of September is flying by, pumpkin spice is back on the racks, the weather is slowly getting cooler, and before we know it, the leaves will be falling, which means that Gilmore Girls season is upon us. (For many of us, it’s already here.)
Just in time for the national holiday, October 8, aka the day “I am an Autumn,” is proclaimed by Richard Gilmore (Edward Herrmann) in Season 1 Episode 6’s “Rory’s Birthday Parties.” So, grab your pizza, popcorn, Red Vines, and coffee, duh, to get back in the Stars Hollow atmosphere.
The heart of the series is, of course, mother and daughter duo Lorelai (Lauren Graham) and Rory Gilmore (Alexis Bledel). Still, through the seasons, they experience their fair share of dates, crushes, love stories, and breakups, making romance an important part of the Gilmore Girls story.
There’s only one way to celebrate the most fall-ish show to (possibly) ever exist: plan out a full rewatch of the now 24-year-old show. Yes, it actually premiered in 2000. We’re all just getting old. But, if you don’t have any time for that, take a look at our ranking of the show’s most romantic episodes across seven seasons.
Gilmore Girls, Seasons 1-7, Streaming Now, Netflix
10. "I'd Rather Be In Philadelphia" (Season 7, Episode 13)
The two leading ladies’ main lovers showcase their devotion in this sad episode. Richard Gilmore is once again in the hospital, and while Emily Gilmore (Kelly Bishop), Lorelai, and Rory are waiting, Luke Danes (Scott Patterson) and Logan Huntzberger (Matt Czuchry) are doing everything they can to provide the care they so desperately need.
Logan tries to borrow a helicopter, Luke is helping out by running errands, and Emily’s caring demeanor never falters.
In good times and bad, your partner should always be there. Like a warm hug on a winter’s day, seeing the two men go out of their way to comfort the Gilmore girls is a relief.
It’s definitely not the most romantic atmosphere, but it’s the lasting effects that allow you to feel held and protected by the onscreen adoration.
9. "Partings" (Season 6, Episode 22)
This addition to the list is rather bittersweet. Yes, it shows how much Rory loves Logan, but it also talks about the reality of a changing relationship. The two unlikely lovers have allowed the other to be fully entrenched in the other’s heart, yet something had always been off.
Was it the different kind of upbringing they had? Logan’s acknowledgment of wealth while Rory acts as if she comes from a completely different world? Rory’s good girl act combined with Logan’s bad boy charm? Or could it possibly just be that Logan moving across the pond is going to throw a wrench in their long-term plans?
During the goodbye party that Rory throws, all of this is brought up and makes the couple question where they’ll be in just a couple of months. Knowing they won’t have the summer romance they wanted, Rory will have to do with her mom and Paris Geller (Liza Weill), will that be enough until they can be reunited again?
8. "Lorelai Out of Water" (Season 3, Episode 12)
Charlie Swan (Billy Burke) makes an appearance in this playful episode, but he’s not the one who makes this so swooonworthy.
Notice how we didn’t even mention his actual name in the series, Alex. Billy Burke will forever be known by his Twilight character and that’ll just have to do.
It’s actually Dave Rygalski (Adam Brody) and Lane Kim (Keiko Agena) who steal the show. The in-love teens are scheming to go to prom together. To do so, they must convince Lane’s mom, Mrs. Kim. This plan hasn’t worked yet in the span of this episode, but his trying is all that counts. This allows the viewers to see what a great guy Dave actually is.
Could he possibly even be the best boy to show up onscreen?
Their relationship didn’t last too long as Dave went on to go to college in California (aka to rebrand as Seth Cohen on The O.C.), but it will forever be cherished within the fandom.
The shenanigans that ensue in the span of 40 minutes were a prime example of their budding love.
7. "They Shoot Gilmores, Don't They?" (Season 3, Episode 7)
Sadly, Dean Forester’s (Jared Padalecki) worst day is also on this list. No, not the day he was caught cheating on his wife Lindsey (Ariel Kebbel) or even when they got a divorce. It is instead the day he realizes that he has lost Rory to Jess Mariano (Milo Ventimiglia).
Although the writing had been on the wall for a while, it isn’t until the danceathon comes along that Dean gets the full picture. Heartbreaking as that may be, Jess and Rory get together, something the showrunners had been teasing from the minute they appeared onscreen together.
Dean is the great starter boyfriend, but Jess is the one who complements Rory the most during that period of time.
6. "Wedding Bell Blues" (Season 5, Episode 13)
After a rough few months, Emily and Richard finally get back together and decide to renew their vows. Lorelai’s parents are difficult at times and steeped in their own ways. But they are nothing short of “couple goals” anyway.
Seeing them apart is heartbreaking as the two just suit each other perfectly. Thinking of the time Emily sternly tells Richard that she’ll be the first to go is a tearjerker and a half. Having them get back together before it’s too late is even better.
Both parties have their faults, yet the celebration of their love is one of the most important dynamics in the series.
5. "Last Week Fights, This Week Tights" (Season 4, Episode 21)
Lorelai and her most compatible beau, Jason Stiles (Chris Eigeman), have broken up. Luke just got divorced, and they can finally share a moment together again.
What does this entail? A dance. Where? Oh yeah, at Luke’s sister Liz Danes’ (Kathleen Wilhoite) wedding to TJ (Michael DeLuise).
The renaissance-fair duo has an eclectic event that takes place in the middle of the town square, and the gazebo becomes the focus of another pair’s love story. Jess’s quirky mother and the charming man-child have a nice ceremony, but it’s Luke and Lorelai who steal the show in this episode.
4. "Love and War and Snow" (Season 1, Episode 8)
There are many moments in Gilmore Girls’ first season that capture the feeling of awkwardness, excitement, and giddiness of having a deeply intense crush. But none of them compare to when Lorelai first spots Max Medina’s (Scott Cohen) broken-down car in Stars Hollow.
The first fall of snow has always been like a secret little gift to Lorelai from the sky, or so she thinks. To have Max there during this must be a sign from the universe, right?
The mother and teacher duo are smirking and giggling the entire night while getting burgers, going to the movies, and walking along the picturesque streets. Not much happens, but it is one of the most purely cute dates in the show.
3. "You Jump, I Jump, Jack" (Season 5, Episode 7)
During her time at Yale, Rory slowly descends into a light version of a brat-fueled legacy of privilege and wealth. The beginning of that is quite cute.
The official start is often said to be when Rory investigates the Life and Death Brigade, otherwise known as Logan’s secret fraternity.
The 1930s wear, not answering questions with the letter “e” in it, and the lavish tents sure make a great setting. So when the “You jump, I jump, Jack” quotable line comes along, the writing is on the wall, and everyone knows that Rory and Logan are meant to be.
In omnia paratus, right?
2. "I Can't Get Started" (Season 2, Episode 22)
This is a jam-packed episode, because not only do Sookie St. James (Melissa McCarthy) and Jackson Belleville (Jackson Douglas) get married, Lorelai and Christopher Hayden (David Sutcliffe), Rory’s dad, rekindle their old flame, and most importantly, Rory and Jess have their first kiss.
Enemies to lovers is an often-used trope, so it makes sense that Gilmore Girls has their fair share of this, too. Rory and Jess might not have been the textbook definition, but they sure fit that description on that faithful day at the quaint wedding.
To this day, a big chunk of the fandom is obsessed with the pairing of the younger Gilmore and the misunderstood, novel-reading bad boy. The lead-up to this event might not have been the best for Dean, however, none of us truly care when Jess is part of the equation.
This should’ve been Sookie and Jackson’s moment, but alas, the start of the blossoming relationship between Rory and Jess proves to be of more cultural importance.
1. "Love, Daisies and Troubadours" Season 1, Episode 21
Another Lorelai and Max episode makes the cut. It’s even crowned to be the most romantic of them all!
After getting together and breaking up, the twosome decides that they can’t really be without each other. Max even has a more permanent idea — what if they get married?
Lorelai kind of agrees but wants it to be a grand adventure, not just a spur-of-the-moment decision.
Luckily for her (and us), Lorelai gets what she deserves: a dozen (or actually way more) daisies in the most romantic proposal of the series.
Alas, they don’t last, but we’ll forever have this episode.
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