Skip To Content

    I Ranked All Of Rory Gilmore's Boyfriends From Bad To Good And, If You Don't Agree With Me, You Can Argue With The Wall

    Rory had some amazing relationships and some REALLY messy ones.

    8. Dean Forester

    Dean leans over the bus seat in front of him to talk to Rory
    The WB

    Boyfriend Rating: -10/10

    Personality Rating: - ∞/10

    Ok, I'll be honest. I truly liked Dean for half of Season 1. But, as time went on, he became more and more toxic. Not only did he give Rory an ultimatum if she didn't say she loves him, but then he became overly possessive of her and jealous of Jess. Dean constantly tells her what to do, complains about the events she invites him to, and yells at her over the smallest things. He also breaks up with her in public TWICE. I honestly don't even know why Lorelai thought he was a nice guy after what he put Rory though. Plus, their immature relationship while he was married was awful.

    His best moment: There aren't too many. But, in Season 1, he asked her if he could kiss her, which was pretty sweet.

    His worst moment: There are too many to choose from. His public outbursts (and dance breakup), his rude comments, or his affair with Rory. However, I HATED his public breakup with Rory in Season 5 at her/her grandparent's party in front of Logan and his friends.

    7. Graham Sullivan

    A close up of Graham as he leans forward in his seat towards Rory
    The WB

    Boyfriend/Date Rating: 4/10

    Personality Rating: 4/10

    Graham and Rory went on one date so there's not much we can grade on. However, he seemed like a decent guy. He was kind for the bit we did see him with Rory. They did not have ANY romantic chemistry whatsoever. But overall, he was fine.

    His best moment: It was kind of him to invite Rory to the bar with him and his friends...but it was kinda awkward.

    His worst moment: You could tell that Rory was uncomfortable during the date and he didn't really do anything to make her feel comfortable.

    6. Paul

    Rory holds a bouquet of flowers while standing next to Paul as they're in front of her front door
    The WB

    Boyfriend/Date Rating: 5/10

    Personality Rating: 5/10

    As we all know and forgot, Rory had a boyfriend in The Year In A Life season. She and everyone in her life forgot he exists (me included). During this season, she keeps planning to break up with Paul, BUT it's no surprise that she always forgets to. We don't see too much to him, but when we do...let's be honest, it's quite boring. The fact the Rory wanted to break up with Paul for months (or however long) and he does it first, and over TEXT, was kinda funny and needed to happen. Their relationship was BORING!!

    His best moment: The breakup text. Considering we thought Rory was going to do it first and he beat her to it was hilarious.

    His worst moment: You can't really have a worst moment when you barely remember him. There I said it.

    5. Robert

    Robert wears a plain t-shirt with a blood stain on it and Rory wears a private school uniform and a long wig
    The WB

    Boyfriend/Date Rating: 3/10

    Personality Rating: 6.5/10

    Of course, since Rory only went on one date with Robert, there isn't too much to rate. However, their date was basically 60% of the episode. To start off, they had ZERO romantic chemistry and it felt awkward the whole time since Logan was on a date with another girl (they weren't dating/exclusive at the time). But, he didn't seem like a bad guy...on the date. This date shouldn't have happened tbh, especially since she AND Logan were jealous of each others' dates. They are better off as friends.

    His best moment: I guess his costume for the party. I mean, there's not much to grade here. But, there's also the fact that he, Logan, Finn, and Colin went out of their way to help Rory though a difficult time in the Fall episode in A Year In The Life.

    His worst moment: Not much him, but this date shouldn't have happened in the first place. It was boring, awkward, he kept talking about himself, and she and Logan low-key wanted to be there with each other instead of their own dates. But, at least we got a Rory/Logan moment!

    4. Trevor

    Rory and Trevor sit next to each other on bar stools in the midst of a crowded bar
    The WB

    Boyfriend/Date Rating: 6/10

    Personality Rating: 7/10

    I'm not sure if I could put this lightly, but this date SUCKED. It was so boring and uncomfortable. Since he was so sweet and nice when they were in class, I thought this date would go well. But, I was so wrong. I'm not sure if it was because it was Rory's first date since Dean or Jess or because of their personalities not hitting it off on a dating level. This date had potential, but just didn't work considering they were better off as classmates.

    His best moment: He was so nice. But, since we didn't see much of him, there isn't a best moment.

    His worst moment: Another worst moment that isn't so much him, but the date itself.

    3. Tristan Dugray

    Rory walks next to Tristan as they head inside of their private school
    The WB

    Boyfriend/Date Rating: 5.5/10

    Personality Rating: 7/10

    I loved Tristan (partly because I love Chad Michael Murray). He and Rory's characters had amazing chemistry and banter. They definitely had the potential to be a couple. Until his character moved away, he was in a good place with Rory. The enemies-to-friends-to-lovers trope worked really well with them. I also loved how he (and a few other of her romances) gave her a nickname. His nickname for her was Mary. They were a wasted potential and a part of me feels like he only teased her because he liked her. But, at least we got a kiss!

    His best moment: I love the party scene moment. No not the kiss (I loved their kiss), but their conversation and how they opened up to each other.

    His worst moment: I didn't like how he kept trying to get in the middle of her and Dean's relationship (even though I hate Dean).

    2. Jess Mariano

    A close up of Jess and Rory as they stand close together with their foreheads pressed together
    The WB

    Boyfriend/Date Rating: 9.5/10

    Personality Rating: 11/10

    Before you go to the comments to hate on why I put Jess at number two, let me start off by saying that I LOVE Jess. He was one of my favorite characters and I loved his relationship with Rory. He was ALWAYS there for her. The fact that he was the "bad-boy" from out of town and only cared about Rory makes him such a great character. He felt so guilty when they got into the car crash and was STILL there for her. He even encouraged her to write a book! Their friends-to-lovers trope was amazing. However, as much I loved them and Jess' character, the reason he isn't in the number one spot is because they're technically cousins after Luke and Lorelai got married. Also, he just left on her graduation day after a fight and never called or texted. Then he just showed up months later begging her to run away with him. However, don't get me wrong, Jess was a great boyfriend and character overall.

    His best moment: When he GOOGLED how far he and Rory were going to be when she went to college. Just so they can visit each other. Or when he fixed the sprinkler and un-did it so there wasn't a problem with Dean.

    His worst moment: When he left without saying goodbye to Rory. It was the one time I hated him. Otherwise, he was witty, smart, and sweet (when he wanted to be).

    1. Logan Huntzberger

    Rory and Logan stand holding hands while holding dark umbrellas
    The WB

    Boyfriend/Date Rating: 100/10

    Personality Rating: 20/10

    There are so many reasons why Logan is at the top of this list. Logan started off as a guy who just dates around with no commitments. But, when Rory admitted she didn't want to be casual, he was willing to be in a committed relationship for her. They had not one, but two meet cutes. Logan started off as a complete jerk, but his relationship with Rory makes you love him even more. He was always a great friend (and boyfriend) to her no matter the circumstance. His "Ace" nickname has also gained him points because it's so cute. Even when the two of them were broken up or in a fight, he was always there for her. Logan loved Rory so much he gave her a rocket to represent their love. They've been though it all and STILL made it though. From judgy parents, to multiple breakups, and almost death. They 1000000000000% belong together.

    His best moment: It's hard to pick just one. But, without a doubt, it's when he refused to show her The Life and Death Brigade because of sworn secrecy. But, since she wanted to learn about it so badly he did it anyways. "You jump, I jump, Jack" still gives me chills to this day!

    His worst moment: When he thought they broke up and slept with all of his sisters' bridesmaids. However, in his defense, he had never been in a serious relationship and didn't think they were still together. It was still kinda messed up because he didn't tell her, which is why it's his worst moment. BUT I still love him and Rory's romance and (to be cheesy) hope I can find a relationship like theirs one day.