The beloved Gilmore Girls revolves around the incredible relationship between mother and daughter duo, Lorelai and Rory Gilmore. As Rory matures, the relationship with her mother changes but the two are still best friends before anything else. Along the way, romantic relationships become prevalent not just in Lorelai and Rory’s lives but in the small town of Stars Hollow.
There were a handful of weddings throughout Gilmore Girls but there’s something special about the engagements. Each engagement was unique and specific to the couple, which is what made them so special. But which comes out on top? Could it have been Logan’s proposal in front of Rory’s friends and family or was it Zack’s quick proposal at the diner?
Dean & Lindsay
It’s not known how Dean proposed to Lindsay but it’s assumed that it happened after the fight with Jess at Kyle’s house. Perhaps he needed to smooth things over with Lindsay after fighting his ex-girlfriend’s new boyfriend? The proposal was suspect because the two were so young and there seemed to be an unnecessary rush.
Regardless of the time, Dean happily told Rory about their engagement but his dreams were dashed when Rory told him he was messing up. Getting married in a hurry just to appease your fiancée was not a good move, and Rory wasn’t wrong. The two got divorced not long after.
Luke & Nicole
Luke and Nicole didn’t last long as a couple and she wasn’t a large part of the series. All in all, it seemed like Luke was only dating Nicole so that he could stop thinking about Lorelai. At the end of the third season, Luke and Nicole went on a cruise. He came back uptight and more on edge than usual.
When Luke refused to tell Lorelai about his cruise, she jokingly asked if he proposed to her. And shockingly, he did. What’s more, he didn’t just propose to her — they got married! The captain of the ship married them on a whim, which made Lorelai want to crawl out of her skin. Not much is known about how Luke proposed to Nicole but getting engaged on a ship sounds more romantic than Dean's proposal.
Lorelai & Max
While most Gilmore Girl fans love Lorelai and Luke together, they can’t ignore her relationship with Max. The two met at Chilton, and even though Lorelai was hesitant about accepting Max’s coffee date, she followed through anyway. The two only dated for a short while but became serious fast.
Max and Lorelai were explosive together and didn’t communicate well. After a frustrating few days for the couple, Max lost his cool when he saw Luke in Lorelai’s house. He became green with envy and ended up telling Lorelai that they should get married. This was clearly done so that he felt secure in their relationship but the proposal was not pure, from a good place, or romantic.
Lorelai declined his offer because it didn’t feel real. However, the next day, the inn was full of 1,000 yellow daisies. The gesture was romantic, but was it perfect? Max wasn’t even there to greet her with the flowers. And when she called him, he didn’t let her speak, he told her that he loved her that she should think about it before answering.
Rory & Logan
As amazing as Dean and Jess were on their own, there was something special about Logan. He was Rory's first serious adult relationship. The two lived together and went through college and long-distance. Logan knew he wanted to marry Rory, so he popped the question in front of a room full of people at her Yale graduation party. Everyone was stunned by the gesture because they were both so young.
Rory didn’t know how to respond at first and pulled him outside to talk it through. She needed a few days to think about it, which kind of put a damper on the whole thing. However, it ended up being the right decision because Rory declined his proposal. She just wasn’t ready and wanted to focus on her career.
Lorelai & Chris
Lorelai and Christopher have known each other since they were kids. Their relationship grew closer and closer and they eventually had Rory. He was the one guy that Lorelai couldn’t quit. No matter how she acted, Christopher always understood and would always be around because of Rory. But when they were finally single at the same time, they decided to give their relationship another chance.
While the two were in France, the moment was so perfect that Chris asked Lorelai to marry him. She was flattered but felt it was too soon. Chris reminded her they’ve been doing this dance for 25 years and if not now, when? Lorelai accepted and the two got married in Paris off-camera. As fans know, the relationship didn’t work and Lorelai should have listened to her gut.
Lorelai & Luke
The night Lorelai picked up Rory from the police station was the worst night of her life. Her daughter had just stolen a yacht and was arrested for it. Things between the ladies only went downhill from there but the one consistent thing in her life that always made her feel better was Luke. After years of being with Mr. Wrong, Lorelai finally found her Mr. Right.
In the middle of Luke’s plan to save Rory from quitting Yale, Lorelai proposed to him. Seeing how much he cared for Rory was the cherry on top. Although they were in the diner and there was no kiss afterward, this proposal came from love on both sides. For once, Lorelai wasn't forced.
Lane & Zack
Lane and Zack were going strong until his jealousy got the best of him and he ruined their one chance at getting a record deal. They broke up and Lane moved back in with her mother. But without Lane around all the time, Zack began to realize what he gave up.
One night while Lane was working at Luke’s, Zack showed up and told her that his life was awful without her. He asked her to marry him in front of everyone and whipped out a ring to prove how serious he was. Lane was taken aback by the gesture and realized how much she loved him. With tears in their eyes, they embraced and kissed in front of the whole diner. Despite how some fans feel about Lane and Zack as a couple, this was a sweet proposal.
Sookie & Jackson
Sookie and Jackson’s engagement was unique because it was after an argument. Jackson was upset that Sookie didn’t want to move in together. But after they talked it over, they realized they were on the same page all along — they were just too scared to be honest about how much they loved each other.
While the two were enjoying a picnic, Sookie told Jackson she was ready to talk about living together but Jackson shot her down. Instead, he asked her to marry him. The look on Sookie’s face said it all. She was in love and shocked and excited all at the same time. It was one of the sweetest moments in the entire series.