My Favourite Gilmore Girls’ Guys!

Emily, Lorelai and Rory Gilmore stand at the graveyard

Gilmore Girls has always held a very special place in my heart. I’ve seen it countless times and it’s always as exciting as the very first time I saw it on television. A huge part of that excitement comes from the romantic relationships involved, and I thought it would be fun to look back and once again live vicariously through Lorelai and Rory’s romantic endeavours. Here are my favourite partners of theirs, and I’ll begin with Rory:

When Rory first started dating, it seemed that she would be the type to go from serious boyfriend to serious boyfriend. It wasn’t until college that she branched out and tried to date. She had a pretty serious crush on her college professor, went on the worst first date ever with a guy her grandmother set her up with, and used someone who genuinely liked her to make her boyfriend jealous at a party. Between all the fun, here are the few boyfriends that stood out amongst the others:

Dean Forester

Rory and Dean looking at each other mid conversation

I questioned whether I wanted to include Dean in my favourites. I’m sorry, but I did in the end because Dean was literally the best boyfriend ever. He was perfect in terms of loyalty, and romantic gestures, and listening. They loved to read the same books, they both love movie nights and going to the cinema, and Dean is open and accepting of all quirky characteristics that Rory and Lorelai share. What’s not to love about Dean?

Rory and Dean have their on again off again moments throughout Gilmore Girls, and in fact Rory loses her virginity to Dean while he is with his new girlfriend. I think this was a low moment for Rory, once she realised what she had done. But she was just doing what we all do at times when things don’t work out for us, instead of looking forward we look back at what we once had brief success in and suddenly feel like we need that back. Perhaps Dean was the best person for this to happen with for Rory. Dean is respectful and patient, and that’s who Rory needed at the time.

I think in a sense that I feel the same way about Dean that Rory does. He was the perfect boyfriend but he just wasn’t right for her. With Dean, Rory could have had the perfect normal life. But like Dean, it would of been a bit too boring for Rory. I feel guilty even saying that, but the only real excitement in the relationship came at the very beginning during the chase, and the fact that he was Rory’s first love. I’m glad that Rory found Dean because she knew how she deserved to be treated from that relationship, but I’m also glad she didn’t stay with him, because there was a lot more excitement to come her way.

Jess Mariano

Jess and Rory stare into each others eyes

Speaking of excitement! When Jess came to town, with every interaction I, and presumably everyone watching, just wanted them to be together already. They had such undeniable chemistry. Jess comes across as a classic bad boy who has a good heart once you get to know him, and Rory seemed to see it almost instantaneously. I think that Jess recognised Rory as a girl who wasn’t the typical girl that would go after him. She wasn’t a dumb blonde who wanted to make out and be bought presents but not actually have any real conversation. Instead she has a personality, she has interests, she is an intellectual and she knows how to stand up for herself.

Jess can relate to this, despite his careless image he too is an intellectual, he reads and has no trouble with school work. The only problem with Jess was that he was trying too hard to rebel. Rory and Jess could have been a perfect match had he had more passion about his future and tried hard to get somewhere. Instead he believed that it wasn’t worth anything and wasn’t willing to listen to those trying to help him, including Rory. In the end that seemed to push them apart.

Again, Rory and Jess reunited plenty of times throughout Gilmore Girls, and honestly their connection and chemistry never wavered. Even at the end of Gilmore Girls: A Year in the Life there is still a possibility that Rory could end up with Jess once they both figure their lives out completely. Jess has succeeded at that point, he wrote a book, he’s a published author, and Rory as a professional journalist could be the perfect pair to him. Sometimes all you need is perfect timing and that’s so hard to come across.


Marty and Rory lie on the couch in front of a pizza box

Let’s be honest, Marty (also known as naked guy) isn’t given a chance at all. Marty unintentionally introduces Rory to Logan Huntzberger and from that very moment Marty becomes almost invisible, especially as a romantic option. Rory is oblivious to just how in love with her Marty is and it’s awkward to watch. Marty could have been a great partner for her. He is fun and he loves food and he has his own quirky cooky side—he would fit right in with Rory and Lorelai! It’s sad that Rory doesn’t consider Marty as a viable option but honestly when you’re going after Logan Huntzberger, there isn’t anything that’s going to distract you from that.

Logan Huntzberger

Logan and Rory sitting at a dining table clapping

Now, I hear some whispers here and there that people may actually not be fans of Logan?! I find this shocking, and I find myself having to defend myself, because Logan is potentially my favourite romantic partner of Rory’s. First of all, nobody could dream of having a ‘how we met’ story that was that magical. To meet the most perfect looking man, who’s a member of a secret society, and be taken to a mysterious place in the woods full of lights and beauty—and that stunt with the umbrellas? That’s a life changing experience, and that bonds you together.

Logan always tried to do the right thing when it came to Rory. He became a one woman man because of how strongly he felt for her. He asked her to marry him because that’s what the next step would be in his world, and while it’s not Rory’s fault that she wasn’t ready, it’s not Logan’s fault that the relationship didn’t work.

I think the pair were wonderful together. They motivated each other and seemed to understand how they were feeling, and after a while they found a comfortable routine together. Rory and Logan are something written in the stars; their lives were simply taking them down separate paths.

In the finale of Gilmore Girls: A Year in the Life Rory announces to Lorelai that she is pregnant, and while we don’t know who the father is it’s safe to assume that it’s Logan’s baby. She has spent years secretly staying with him when she visits London, and this type of thing could give them both a clue and get them back on track to being together.

We will probably never know for sure who Rory ends up with but in my mind I picture her life with Logan.

Lorelai, Rory and Luke posing for separate pictures

Next let’s move onto Lorelai Gilmore and her collection of classically handsome men.

A few of Lorelai’s shorter relationships seem to disappear from my memory as soon as they’re over. Alex and Jason Styles for example were exciting in the beginning but Alex didn’t do anything memorable at all, and Jason pushed the boundaries of the moral and comes across quite unlikeable.

Perhaps the funniest part of Lorelai’s romance was being asked out by Kirk. What made it even more hilarious was that Kirk actually thought she may say yes. We can’t feel too guilty about laughing at Kirk considering it all worked out well for him, and it did for Lorelai too.

Christopher Hayden

Lorelai and Christopher kiss

I almost feel like I have no choice in putting Christopher into my favourites. He is the father and the high school sweetheart, and he rides a motorbike (they always do, don’t they?). Christopher is on paper fantastic for Lorelai and it would make perfect sense for them to be together, but it’s like Lorelai said, he is the man that she wants to want, but not the man she does want.

I think in the end Christopher offered her a safe kind of love, but for the longest time he was someone she couldn’t trust to even be around for the rest of the week. They had plenty of benefits, in that they had known each other for years, understood each other, had the same taste in music, could make each other laugh, had both escaped from the same way of life, and they did all that together. They were bonded, but a woman like Lorelai deserved more unfortunately, and Christopher seemed to know that.

Max Medina

Max and Lorelai look down at the engagement ring on her hand

I’ve come to learn that Max is often the favourite when it comes to Lorelai and her relationships. Max  is dreamy, and he’s an English teacher. What makes Max perfect for Lorelai I think is that he is accepting and patient. He didn’t even respond angrily seeing Lorelai after she basically ran out on their wedding the night before. Max would have loved Lorelai through most anything she could have done, which was proven when he still wanted her back after that event, and Lorelai knew that. Just like with Christopher it offered her a feeling of safety and security, and that’s the one thing she needed and couldn’t find where she was looking for it.

Max and Lorelai could have gotten married and lived a perfect life, with Rory too, and it would have been a fairy tale romance. Their wedding party was definitely a fairytale in itself, but like Christopher it just wasn’t right in her heart. He wasn’t the one. Which brings me to…

Luke Danes

Lorelai and Luke getting married

Luke is the one. Luke has always been the one, and we knew it since the very first episode when we first saw him and Lorelai pleaded with him for a cup of coffee. They have that chemistry that you can spot from another galaxy, and still recognise that they are destined to be together. It’s always the case in this situation that the pair are blind to their own romantic connection. It’s like Joyce and Hopper in Stranger Things. The mocking and the sarcasm and even insults come from frustration of being so deeply in love with the person but they don’t even see it. It was surprising in this case that Luke was the one to realise that he wanted Lorelai through a self help book. And the magic began right there when he took her to his sisters wedding.

Luke did some questionable things, and so did Lorelai. Luke hid the news of his daughter, and was rather insanely jealous of Christopher, which turned out to be justified when Lorelai slept with Christopher after an argument of theirs. But they came together despite everything. In Luke’s case, it’s not saying ‘he would do anything for her’—it’s genuinely saying ‘he did everything for her.’

Luke is the one because he is a father to Rory and loves her as his own, he came running whatever circumstance he was in when Lorelai needed him and never questioned when helping. He spent countless hours fixing things at the house and the inn and could be convinced to do anything when it came from Lorelai. He even built her huppah for her wedding to another man because he wanted her to be happy.

That is a relationship that is going to last a lifetime. I am so sure of that. Luke Danes is the man who finally got Lorelai Gilmore down the aisle.

Emily and Richard Gilmore


Emily Gilmore is the original Gilmore girl, and while she and Lorelai have had more than their fair share of troubles I think one thing that Emily set a perfect example for is how to have a long lasting marriage. Richard Gilmore married and loved Emily despite his mother’s disapproval, he supported his family financially and through working himself to the point of illness. Richard Gilmore is arguably the Gilmore guy we should all favour, as he is the most respectable man that I know.

Richard Gilmore is portrayed by Edward Hermann, a man who is somehow even more respectable than his character. Edward is a beloved member of the Gilmore Girls family who passed away in 2014 from brain cancer. You probably recognise Edward Hermann as Max in The Lost Boys, or as F.D.R in Annie, but Edward blessed 154 episodes of Gilmore Girls with his wonderful lively presence  and became a cast member that the show didn’t want to live without. He created an everlasting relationship with his on-screen wife, portrayed by Kelly Bishop. In fact, they thought so fondly of each other that Kelly was the only person invited to join his family during the final week of Edward’s life.

I want to express my love and gratitude for Edward Hermann and his portrayal of Richard Gilmore. Both men represent ambition, power, passion, love and humour too. I have spent time with both Richard and Edward through my television over years of my life and they have both made me laugh and made me cry. I adore them both. Richard and Emily paved the way for the future of Gilmore Girls romances and they had a marriage that proved inspirational to us all.

So, to conclude, the Gilmore Girls and their romances are quite a wild adventure, but when it comes down to it I believe Rory and Logan and Lorelai and Luke are those who are written in the stars, and they find their way back to each other in the end. I believe that in a universe where Gilmore Girls lives on, Rory and Logan find a way to live together openly and start a family, and he finally gets to give her that ring. And for Lorelai and Luke, I think they’re perfect staying the way they always have been.

Written by Abbie Sears

Abbie is an author for 25YL from the United Kingdom. She has a passion for meditation and travel. She loves concerts, drumming, playing indie games and binge watching shows.

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