If there was one couple on Gilmore Girls you could put in a yearbook, it was definitely Rory and Dean. These two met in high school and were cute as a button until their love story ended (although they did rekindle a little something-something when Rory was in college). Still, the competition for the title of Best Gilmore Girls Boyfriend is fierce (it’s probably even more controversial than your political party of choice), and in the wake of all of Rory’s former suitors returning for the Gilmore Girls: A Year In The Life revival, it's worth remembering where Rory and Dean ended on Gilmore Girls .
I’ve always been torn on Dean. He was nice in some aspects, and as Lorelai says in the series, the "perfect first boyfriend" for Rory, but I was never a fan of his borderline patriarchal mindset. The whole Donna Reed thing always put a bad taste in my mouth — Dean had these views that women should strive for nothing more than to care for their families, and even though Lorelai and Rory raged against his machine when he brought it up, Rory still changed into a Donna Reed costume to cook him dinner at the end of the day. I always felt like Dean’s kindness overshadowed the fact that he was still pretty controlling. Even so, Rory and Dean did get back together for a blip toward the end of the series. Let’s see where they left off.
Rory leaves Stars Hollow High School very early at the beginning of Gilmore Girls, but not before meeting Dean. Their courtship is fairly easy and nice — you know, normal high school stuff. First kiss, first dance, etc. The two date for most of Season 1, but Dean goes a little too hard, too fast and freaks Rory out. He restores a car for her and tells her that he loves her, and Rory says she needs more time to process this. They break up and both sulk around Stars Hollow, and, as young sweethearts often do, promptly get back together. This time, Rory is able to respond with “I love you, you idiot.”
Things are going just fine until Luke’s nephew, Jess, shows up. He and Rory have instant chemistry, and as Jess and Rory start spending more time together as friends, Dean gets more and more jealous. Dean thinks Jess is no good, and Jess thinks Dean is a square. Dean is distraught that he might be losing Rory, but Lorelai gives him the advice to back off and make Rory miss him. After the 24-hour dance marathon, Dean knows that Rory has feelings for Jess, and the two break up in a very public, very ugly way. Sigh. Rory and Dean later try to be friends, but once he starts dating Lindsay, it’s awkward. Even more awkward is when Lindsay and Dean get engaged and Dean admits to Luke at his bachelor party that he’s still in love with Rory and would rather be marrying her. But Lindsay and Dean get married anyway.
Rory is at Yale, but she and Dean get close again, and as that’s all happening, Dean’s marriage begins to fall apart. Wonder why. Probably because Dean was spilling all of his marital secrets to Rory and Lindsay found out. At the opening of the Dragonfly Inn, Dean and Rory almost lock lips. They are interrupted, but just when you thought it was safe to go back in the water, Dean and Rory have sex (it's Rory’s first time). Oh boy. Lorelai comes in at the end of it all and is not pleased with her daughter for having sex with a married man. Rory is convinced that Lindsay and Dean will split (because that’s what he told her), but oh honey, no. Rory and Dean then try to talk about their tryst and end up having sex again.
Rory knows that what she is doing is wrong, writes Dean a letter to break their affair off, and unfortunately, Lindsay finds it. Lindsay and Dean split, and Rory and Dean give their relationship another go. This time, though, Rory is at Yale and Dean is working four jobs and it just doesn’t work. Lorelai also doesn’t approve of the relationship, so that doesn’t help. Rory and Dean finally end things with help from Richard and Emily, who arrange a party to help Rory meet a new, suitable beau. Dean takes one look at the men at the Gilmore house and knows he doesn’t belong. They break up again, and we don’t see Dean and Rory together for the rest of the series.
Images and press from the set of Gilmore Girls: A Year In The Life indicate that Dean is indeed back for the revival, but if his time will be spent with Rory remains to be seen. Personally, I think he’ll make an appearance just because he’ll be in Stars Hollow, but there’s no reasoning with the heart.
Images: Warner Bros. Television; Giphy (3)