Every Proposal on Gilmore Girls Was Absolutely Unhinged
This show was rich in couples, swimming in conflict, and desperately lacking in healthy communication. Which made for some batshit marriage proposals! Let's go:
Christopher to Lorelai in Season 1 ep. 15: Christopher Returns
In Christopher's first appearance on the show, he rocks up to Stars Hollow on his motorcycle at the end of the previous episode, out of the blue, and in this one archetypes are made clear: he establishes himself as the irresponsible deadbeat single dad to Lorelai's hardworking, mature yet still fun single mom. They have a weird dinner with everyone's parents where his parents, Straub and Francine, are shown to be even more uptight and awful than Richard and Emily can be. A lot of fighting and yelling and relitigating past choices ensues. Then Lorelai and Christopher go off to have emotional, nostalgic sex on her childhood balcony, and off the strength of that, he walks into her kitchen the next morning and blurts out that he wants to marry her so they can be a "real family". They barely see each other. They know hardly anything about each other's current lives. This is the first time he's visited the town they've been living in since Rory was a child and yet. A marriage proposal. Naturally, she turns him down, but we have not heard the last of Christopher Hayden.
Max to Lorelai in Season 1 ep. 21: Love, Daisies and Troubadours
This relationship was used mostly to discuss Lorelai's commitment issues, the difficulties of dating as a single mom, and have her fight allegations of her being promiscuous (which are not true, she can be very sexually conservative) by having her do something risky like try to date one of her daughter's teachers at the stuffy private school that also exists in her parents' world. So despite them having okay chemistry, they haven't really dated much and broke up after two months before getting back together shortly before the night of the proposal. Max comes by the house to pick Lorelai up and finds Luke there getting his toolbox and relaying the news that Rachel broke up with him (because she has a basic level of intuition and picked up on his feelings for Lorelai). Max and Luke have a very cringy dick measuring contest, Max (in possession of similar intuition) assumes Luke and Lorelai dated at some point but it's not season 5 yet so she's not legally allowed to admit she's into Luke. They argue, Max expresses frustration that their relationship can never seem to get off the ground, and what does he propose as a solution? Yoking their lives together in blessed matrimony. Lorelai is justifiably frustrated and tells him that's not how you propose, that a proposal is supposed to be special and grand. She lists "a thousand yellow daisies" as an example how to truly pop the question and the next day Max arranges for that famous logistical nightmare romantic gesture at the inn, then says some flowery bullshit on the phone and because it's the season finale and emotions are high, Lorelai accepts. Though later, right after her bachelorette party, she runs away and calls off the wedding. They meet a couple more times for closure, and then the relationship is truly dead.
Jackson to Sookie in Season 2 ep 13: A-Tisket A-Tasket
Sookie and Jackson's budding relationship has actually been pretty nice to watch up until this point. They have a fun balance between awkward but cute flirting and comical bickering about produce. But there's something in the area's water supply that makes people unable to clearly express their wants and needs in a romantic relationship so when Sookie doesn't respond how Jackson wanted her to to him saying his lease was up and asking her what she thought, he sulks. The sulking manifests itself in him not bidding on Sookie's basket at the bid a basket auction so she confronts him to see what's up and they actually manage to have a decent conversation about what moving in together would mean. And that could've been a nice ending for that storyline. But shacking up together? Out of wedlock? Impossible. So at their picnic for two, Jackson fakes Sookie out and says he doesn't want to talk about moving in together any more... because he thinks they should get married. Sookie, reeling from that whiplash, accepts, and since the rules of TV beta couples states they must move faster than the main will-they-won't-they couple at all times, they get married, stay married, and continue struggling to effectively talk through big life decisions,with some admittedly nice moments in between.
Lorelai to Luke in Season 5 ep 22: A House is Not a Home and Season 6 ep 1: New and Improved Lorelai
Lorelai and Luke are in kind of a weird place at the moment, with Luke upset with Lorelai for considering selling the Dragonfly to a corporation owned by one of her father's contacts, which would have her traveling and consulting instead. While she's not too serious about it, she's enjoying being courted by the company, but this is in complete disregard for the giant house Luke bought without telling her or the kids he's thinking about having that he also hasn't discussed with her so it's causing problems. This is forgotten however with the news that Rory wants to take time off from Yale after receiving some rare negative feedback, and that Richard and Emily are letting her stay with them after just telling Lorelai they would help her force Rory back into Yale. So when Lorelai walks into the diner lamenting the fact that Rory is making a decision independent from the vision Lorelai had for her life, and Luke comes forth with a nonsensical plan to, again, force Rory back to Yale, Lorelai is touched that she finally has someone on her side. And since she's a veteran of the season finale marriage proposal, she celebrates having her partner agree with her by asking him to marry her. He accepts in the next season's premiere with no hesitation, but eventually their tendency to hide things from each other to not ruin their relationship.... ruins their relationship. Shocking.
Zack to Lane in Season 6 ep 16: Bridesmaids Revisited
Zack is on a bit of a redemption tour after ruining Hep Alien's showcase in front of a major label by throwing a tantrum about Brian potentially writing a song for Lane. This random burst of jealousy sends him on a power trip that has him throwing out their set list and screaming at his band mates until a fight breaks out and the band and him and Lane split up. But when he sees Lane in the music shop some time later putting up a flier advertising her drumming services to other bands, the thought of her daring to potentially continue living her life without him spurs Zach into action. He convinces Brian and Gil to get the band back together and they're in if Lane's in. And his way of getting Lane back is to walk into Luke's while she's working, go off on some tangent about how he doesn't feel good, and propose in front of a huge crowd of gossipy small town people. Lane must have smacked her head on some antique furniture that day because although she at least stops to ask if he's thought about this, when he presents her with the pawn shop ring he got that "belonged to like an Elk or a Moose or something", she accepts and walks right into marriage and babies land and right out of development that would make sense for her character or be interesting.
Christopher to Lorelai in Season 7 ep. 7: French Twist
Ever since Lorelai walked out of her fraught engagement with Luke and into Christopher's bed, he has taken the reality of a woman coping with feelings of rejection by hooking up with the man she keeps stashed in the background for occasions such as these, and spun it into an elaborate romantic tale of two star crossed loves who waited their whole lives to be together. And when Sherry who, guided by the hands of karma, previously abandoned Gigi leaving Christopher to raise her on his own, writes a letter saying she's totally fine now trust her and wants Gigi to spend a few months with her in Paris, Christopher invites Lorelai along for a big romantic gesture trip. They spend most of it jetlagged, but Christopher remembers he's super rich now (as opposed to just being regular rich like before) and he bribes a restaurant to open early for the two of them. Lorelai, basking in the romance™ of it all, confesses her love, and Christopher pounces on that and starts in on a whole speech. Basically, even though he said he'd be willing to wait for Lorelai to fall in line with his vision, he doesn't feel like waiting any more. Lorelai, sensing where this is going, suggests they wait, as they've only been really dating for a couple of months. She also brings up Rory, figuring she'd want to be up to date and present any big changes. But Christopher waves those perfectly valid concerns away, stresses how long they've known each other, insists that they're meant to be, and fate has brought them together. And then comes out with it and asks her to marry him. Which are very intense words for Lorelai, an emotionally vulnerable woman who just broke off an engagement because her fiancé seemed overly hesitant to actually get married, to hear. We don't see her accept, but there's a scene of them returning home where he calls her "Mrs. Hayden" (as if she would ever change her name), and their marriage immediately began to fall apart like wet tissue paper.
Logan to Rory in Season 7 ep. 21: Unto the Breach
It's the end of Rory's time at Yale, and on the heels of her New York Times fellowship rejection, rejections from other newspapers across the country, and the fact that she rejected her one job offer for better things that did not come, Rory's future is wide open and unstable. On the other hand, Logan is completing his character transformation from irresponsible party animal trust fund kid to hardworking and responsible trust fund kid, accepting a job offer for an internet company in San Francisco. The question emerges: How will the young couple handle this next phase of their lives? And when Logan shows up at Lorelai's house in the previous episode, he comes with a solution. He wants to marry Rory and take her to California, and he wants Lorelai's blessing to propose. She gives it, though not without trepidation, and Logan does propose. In the middle of the graduation party Richard and Emily are throwing for Rory, he gets up in front of everyone and takes out the ring. Rory is caught completely off guard and takes him outside to talk about it, where he reveals that he got the job, picked out a house for them to rent, researched newspapers where she could apply to work, and even planned activities for them to do in their spare time. The original plan being that she would say yes to his proposal without knowing all this and walk blindly into her new, pre-arranged West Coast life. But Rory needs time to process the idea of marrying Logan immediately after college, and on the day of her graduation, she declines. Logan decides if he can't marry her, there's no point in being with her at all, and the two go their separate ways, to eventually meet again in a years long affair, for some reason. Though I barely acknowledge the revival.
Honestly, the only proposal that truly makes sense is Lorelai's to Luke in the revival but I won't discuss it here because a) again, the revival basically doesn't exist to me and b) they should've married during the original run of the show.
