The Fates of Rory’s Boyfriends – Revisited

Before the Netflix revival of Gilmore Girls (A Year In The Life) came out, I wrote a post where I speculated the fats of Rory’s boyfriends. Shockingly, it was titled The Fates of Rory’s Boyfriends. I know. I’m so original. I thought that since now A Year In The Life is out, I should revisit the post and see if my predictions were correct!

Now, some of the boys that I speculated about weren’t featured in AYITL, so we can just assume that I am 100% right about them, right? Good, glad that we all agree, and I’ll just skip over those guys. As for the others that were included, I think I wasn’t that far off!

Dean – Oh Dean. Your future is not so bright. After breaking up with Rory for a third time (outside of Richard and Emily’s male Yale party, remember?), life was not kind to Dean. It wasn’t bad, just not awesome. He stuck around Stars Hallow for a little while (still living at his parent’s house and all) but he finally moved to the neighboring town of Woodbridge, where there seemed to be more opportunities for a young person who is kind of good at carpentry. He got super into Crossfit and has a man bun right now. He tried to rekindle things with Lindsay after a few years had gone by, and they were together for about 8 months, but she broke it off again when she realized he would never truly be over Rory. He is currently still single, but has “dated” every girl in his Crossfit box at least once. Revisited: So I wasn’t completely right about Dean… Although my guess could have totally happened, we don’t know! I was happy to see that he was happily married with kids, though.

Jess – I say yes to the Jess! (Gilmore Guys reference there, for any other Gillies reading!) Jess lived in Philadelphia for a while, working for the small publishing group and continuing to write in his spare time. He has published a book of essays and a full-length novel, which became marginally popular and is currently being made into a movie. Jess eventually moved to New York City where one of his essays is being produced into a play (it’s off off Broadway- don’t worry, Jess did not sell out.) He sees Rory from time to time when she is in the city, and they always enjoy catching up as old friends. Revisited: I was partially correct when it came to Jess! He became successful (in that he isn’t homeless) and has matured, and it was made pretty clear that he and Rory kept in touch every now and then over the years. One thing did become very clear in the revival tho… Jess is WAY too good for Rory! Go get someone better!

Logan – Logan won’t let a break up get him down! He did go to California like he planned, and had a fun time while there. He sold back the engagement ring and used that money to pay for a weekend in Vegas with Colin and Finn to drown his sorrows celebrate being a bachelor. He is rising in the ranks at his job and has merged his company with his family’s making himself a business tycoon. He has been engaged once, but called off the wedding when he realized that his bride-to-be was more interested in his family money than him. He is currently dating someone but has no desire to settle down for a while. He keeps an eye out on Rory’s career (from a distance) and had someone offer her a job at one of his family papers in NYC. Revisited: So I was kind of right here… Logan is still kinda slimy and is obviously doing well in his professional life. Clearly he is not ready to settle down (even though he is engaged) since he is cheating on his fiance with Rory. Boo.


Doyle – While Doyle and Rory weren’t actually interested in each other, he did awkwardly kiss her that one time and that means he gets added to this list. Doyle did follow Paris to her grad program and followed her again when it was time for her residency. They got married and Doyle likes to joke about that drunken kiss whenever Rory comes to visit them and their kids. (Paris does not like those jokes, tbh). Revisited: Doyle and Paris DID get married!!! But now Doyle and Paris are splitting up. Womp womp. I really like to think that they figure out a way to stay together, because Paris and Doyle are the best!

Tristan – Military school was very good for Tristan. He shaped up and began to see the potential in him that Rory always knew was there. He went to college at Dartmouth and kept waiting for Rory to join Facebook so that he could send her a friend request. He finally tracked her down and sent a quick note to say thanks for believing in him, which she thought was very nice. Tristan got a job at his father’s company, lives in Connecticut, and married a nice society girl who is also in the DAR. He ran into Rory once when she was back in Hartford visiting her family and they said they would keep in touch. She gets a Christmas card from Tristan’s family every year, but that’s about it. Revisited: So we didn’t actually get to hear from Tristan, and we didn’t even see the REAL Tristan (lame actor stand-in….psh) but the fact that he came back for the alumni day at Chilton means that he probably lives close by, so I’ll assume I’m right about him.

Robert (Logan’s friend that took Rory to the Quentin Tarantino theme party) – Robert thought all of his dreams were going to come true. His parents died early (sad for them, but Robert was always kind of awful and didn’t mind) and left him all of their money, which he then blew through within 2 years on vacations and building a giant mansion. He now shares this giant mansion with 42 roommates just to pay the bills. Revisited: We actually see him again! We see that he is still just as ridiculous as ever. If he hasn’t blown through all his money yet, then he will soon if he keeps being crazy with the Life and Death Brigade boys.

So while I didn’t get everything right, I didn’t get everything totally wrong, either! I like the way the characters turned out on A Year In The Life, but I also like the fake lives I gave them, too.


5 thoughts on “The Fates of Rory’s Boyfriends – Revisited

  1. I want to hear your take on Marty! I have a friend who loved Marty the best (even though he dated Lucy and lied about knowing Rory). Whatevs…I’m Team Jess for life…even if he is TOTALLY too good for her.

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