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Every “Gilmore Girls” Love Interest, Ranked From Worst To Best

The amount of time Julia Pepperwood and I have spent discussing the “doability” (technical term) of Gilmore Girls characters is, frankly, embarrassing. It started with your typical Jess vs. Dean debates in high school and has since evolved into dissecting the pros and cons of EVERY male character over Gmail. You get the idea.

Since there is no official document to reference when having such debates, I’ve decided to create a definitive ranking for the world to use (I’m sure the Smithsonian will be calling me soon to request the original copy). Since Stars Hollow has dozens of characters, this list only contains the “love interests,” meaning guys Lorelei and Rory have dated, flirted with, married, etc. I also included the beaus of the Honorary Gilmore Girls, aka Lane, Paris, and Sookie, to reach a grand total of 24 men. Please feel free to tear this list apart with your own rankings.

24. Jason Stiles

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I HATE JASON. He’s nothing more than a rapacious little rodent. He doesn’t know how to have fun (he even trained his dog to be boring), is objectively unattractive, and generally lacks a soul. Let’s be real, Lorelei was only with him to get back at her parents.

23. Asher Fleming

asher

Pros: British, smart. Cons: Semi-pedophilic, deceased. NEXT!

22. Rune Belleville

rune_final

Bahahahaha. Oh Rune. I’m including him since he did go on one (disastrous) date with Lorelei. I wish he existed in real life, because I find him to be extremely entertaining. But if there’s one thing Rune is NOT, it’s doable.

21. Young Chiu

yiung chu

Poor Young Chiu. He starts out as Lane’s Korean fake-boyfriend, but then falls in love with her for realsies and becomes super clingy. We all know that clingy = turn-off. I’m sure he went on to have a very promising career in medicine, so I don’t feel guilty putting him in the bottom 5.

20. Airhead Todd

todd

ICYMI, Todd is the boy Lane had a crush on, until she discovered he’s a moron (an endearing moron, to be fair) during their double date with Dean and Rory. We can all learn a vital lesson here: If a boy’s favorite movie is Beethoven, he is not worthy of your love.

19. Hot TA

hot TA

Remember the TA that subbed for Richard after his heart attack? He was CRAZY hot, as indicated by Rory’s CRAZY awkwardness around him. Unfortunately, he only spoke somewhere around 20 words during his episode and then never appeared again, so I have no way of figuring in personality points. In order to make myself seem less shallow, I’ve ranked him relatively low.

18. Dean Forester

dean

I feel sorry for Dean, because the Gilmore Girls writers clearly had it out for him. They turned him into a stupid and violent idiot, when he was devoted and at least decently witty in the early seasons. But even when I keep that factor in mind, I still hate Dean. He was needy and manipulative pretty much from the beginning (breaking up with Rory when she wasn’t ready to say “I love you” springs to mind). And then there’s the obvious fact that he cheated on his wife. ALSO, did anyone else ever notice the serious sexual tension between him and Lorelei? I’ll pass on the Mrs. Robinson crap, thank you very much.

17. Zack Van Gerbig

zach

I really want to trust Lane’s judgment, but Zack doesn’t do it for me. I don’t think he’s capable of providing for me or even himself, seeing as he’s dumb to the point of being mentally ill. And his meltdown during Hep Alien’s big break was a major turnoff. Nice hair, though.

16. Robert Grimaldi

robert_final

Robert is attractive, although he’s a bit of a snob and sounds like Patrick Bateman when he talks. His role is small, but judging by his group of friends and what few lines he does have, we can assume he’s probably a total a-hole. I will give him major points for creativity—dressing up as Dead Extra #2 to a Quentin Tarantino-themed party is awesome.

15. Trevor

Trevor

To refresh your memories, Trevor is the boy who sits on the same side of the table as Rory when they go on a date, which just so happens to be one of my pet peeves. On the plus side, he’s very friendly and cute, albeit a bit boring. He deserves a solid middling position here.

14. Logan Huntzberger

logan

I don’t care how many “I’ve changed my ways” speeches he gives—I’ll always see Logan as an immature snoot face. That type of pretentiousness he oozes is deeply ingrained, my friends. But holy moly, is he cute. And loaded. And wicked smart … maybe even smarter than Jess (gasp!).

13. Doyle McMaster

doyle

I tend to get along with neurotic people fairly well, so I could see myself being Doyle’s friend IRL. And he actually has decent boyfriend potential—he’s devoted and supportive and funny—but I think that’s 99% because Paris is his perfect match. I don’t think I would have the patience as a girlfriend to get all of those lovely qualities out of Doyle. Plus, he’s crazy short.

12. Christopher Hayden

christopher

Christopher is hot, rich, smart, and proooobably Lorelei’s actual soulmate. But he’s also a huge baby and borderline alcoholic. If he could figure out a way to sort through his textbook daddy issues and overpowering fight-or-flight mentality, then yeah, he could get it. I mean, remember when he played Funny Face on the side of a barn for Lorelei? Swoon.

11. Henry Cho

henry

Henry is adorable AND on his way towards becoming a (rich) doctor. He put up with a lot of crap and secrecy in order to hide from Lane’s mom, so major points for perseverance. Yes, he does get fed up and asks another girl to prom, but there is a limit to how much energy you should be expected to put into a high school relationship, so I’ll let it slide.

10. Jackson Belleville

jackson

He may sleep with zucchini and wear a goobery hat, but Jackson is easily one of the nicest people in all of Stars Hollow. He has a teddy bear cuteness and is constantly proving his love to Sookie … except for that time he lied about getting a vasectomy. That knocks him down a few places in this list.

9. Max Medina

max medina 2

Max Medina is the ideal man on paper. He’s romantic and passionate, smart and attractive. It never totally worked for me in real life, maybe because Lorelei didn’t love him, so we weren’t supposed to love him? Or maybe it’s because he’s wonderful, but WAY too malleable? He’s a great guy altogether though, so I’m sure he’ll end up with a beautiful woman with whom he can discuss literature and whatnot.

8. Alex Lesman

alex

Alex is one of the good ones. He’s pretty dreamy and owns his own chain of coffee shops, so you’d probably never have to pay for a latte again in your life. Honestly, he’d have made it into the top 5 on my list if he wasn’t played by Bella’s dad from Twilight. I have trouble moving past that.

7. Marty

wayne1

Marty is really cute in a John Mayer sort of way, plus he’s quippy and has good taste in movies. And his Season 7 douchiness is entirely out of character, so I blame the writers for that one. My only qualm is that he’s kind of a Debbie Downer and can be self-deprecating to the point of awkwardness. I think once he grows up, gets a real job, and gains some confidence, he has the potential to be a real winner.

6. Peyton Sanders

jonhamm

Okay, Lorelei. If a man who looks like JON HAMM wants to take you on his PRIVATE JET to see a DAVID BOWIE concert, you go. And then you marry him, regardless of how “boring” he may or may not be. Any questions?

5. Tristan DuGrey

tristan

Tristan is kind of like Logan Huntzberger: The Early Years, except all of those negative qualities—snobby, rude, rebellious, etc.—were 10x funnier when Tristan displayed them than when Logan did. It’s probably because Tristan had a shorter stint on the show and never actually dated Rory, which allowed him to remain a sort of bad boy fantasy. Personally, I would marry a person named Tristan DuGrey in a heartbeat, because that ish is straight out of a romance novel.

4. Luke Danes

luke

It’s kind of annoying when a show clearly wants you to root for a certain couple, like Gilmore Girls did with Lorelei and Luke, but I still really like Luke Danes as an individual. He’s easily the most dependable person on this list, and there’s nothing wrong with a handsome man who knows how to cook. I do worry that his grumpy disposition would start to bum me out ’til death do us part, so he’d have to work on that.

3. Jamie

jamie

Jamie is kind of perfect, and Paris totally took advantage of him. I mean, he’s really cute. And smart and nice, I guess, but mainly cute. I’m not even going to dock points for his incessant phone calls and impromptu visit to Yale, because that’s just what needed to be done during Paris’ neglectful, Asher-snogging phase. Jamie, you can call me anytime.

2. Jess Mariano

jess2

Jess is brilliant, gorgeous, and a good kisser. He’s also kind of a dick, especially in the earlier seasons, but we can write that off to youthful rebellion. Because at the end of the day, you know he’s a good person. He learns to appreciate Luke AND is the one who convinces Rory to put herself back at Yale. Um, plus he goes on to write a book, which is sexy to the max. I’ve been #TeamJess since the beginning, and I daydream about him eventually ending up with Rory (or me, if she’s not interested).

1. Dave Rygalski

dave

Our #1 spot has to go to Dave Rygalski. He’s devoted without being a stalker, jumps through some serious hoops to be with Lane, and is just plain adorable (Adam Brody, duh). He also left the show abruptly to star on The O.C. attend college in California, so he never had to be cursed with a douchey storyline. Dave, you will forever be our favorite Gilmore Boy and the one Lane should have ended up with. Sorry, Zack.

davekiss oie_N09VpdjvuQql

And just to make sure I end on a high note, I present to you the greatest picture ever taken:

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14 thoughts on “Every “Gilmore Girls” Love Interest, Ranked From Worst To Best

  1. Oi, with the poodles already – I freakin’ love your list! My only real contention is that I would definitely up Max’s ratings to 4 or 5 (but, then again, I am a grad school literary nerd). Other than that, I’m so with you! And putting Dave and Jess in the top two – yep!

  2. lol don’t agree on a lot of these but fun reviews, I mean in know Jason had a lot of issues (I mean the dog was creepy) but you seriously put Ruuuuuuuuune ahead of anyone on the planet lol? And eeeeeeewwww Asher, Asher and Rune should have competed for last place.

    • I ALMOST put Asher in last place, because ew. But Rune just makes me laugh way too much to rank lower than Jason, who NEVER made me laugh. What can I say? I like ’em funny.

      Thanks for reading 🙂

  3. I’m always a Jess girl…from day one. Even after he broke her heart. I’ve always hoped that after leaving Logan and embarking on the campaign.trail and becoming some renowned political blogger and journalist that she ended up in Philadelphia with Jess. And he proposed to her by writing in the margins of a book. Jess is my #1. Also, I just realized I’m a huge 29 year old GG nerd.

  4. In my own world, it’s:

    1. Jess
    2. Luke
    3. Dave
    4. Jamie
    5. Marty
    etc.

    But, your rankings, and reasons for them, are generally very good. I would have put Zach higher on the list and Christopher lower…and Peyton’s “good points” are the same as Logan’s so…if he’s dull to the point of being painful to spend an evening with…no thanks! Also, though he’d be on the bottomish end of the list, you forgot Graham Sullivan, the guy Emily set Rory up with and whom she subsequently joined for the beginning of a pub-crawl. I always found it ironic how turned-off Rory was by him and his friends’ alcohol-soaked ways, considering how quickly she adapted to them with Logan and Co.

  5. Youre missing the dude from Lorelai’s business class (I cannot remember the name right now). The one who is much younger than Lorelai and the town gives her a hard time for it. He was cool enough (and with only one date, STILL better than Jason haha)

    I would also put Jamie and Luke before (so, better than) Jess. Just cause they were better partners to their respective lovers than Jess was.

  6. I’m now rewatching Gilmore Girls, interesting how the guys I liked so long ago aren’t interesting anymore.
    I don’t like Dean anymore, but I did when I was a teenager. Now I find him boring and needy. I found Max so… blah… before, and now I found myself rewinding his scenes with Lorelai, he is very hot 😀
    I’m still ok with Luke (the character), but I don’t like Scott Patterson he is a pretty weak actor considering the rest of the cast.
    The only think that hadn’t changed is the fact that I still hate Jess. Emotionally pretentious, immature, cowardly, whiny…. grrr… never had patience with guys who can’t say what they want and then act out. Just want to punch him every single time I see him.
    I still like Tristan maybe because we never really got to know him… but I don’t find Logan as fun or cute anymore.

    I think it’s great that the guys on the show were so different from each other. There is someone for everyone (to like) and it’s fun to rewatch the series and see how much You changed your preferences. 😉

  7. Oh my gosh yes totally I love that you have Jess and Dave in the top two and I totally agree about dean and Logan 🙂

  8. Okay, so I know I’m a guy commenting on the love interests of female characters, but I have opinions too. Lol. I’m the same personality type as Lorelai; agree with her about 98% of the time. So, I also thought Dean was a good 1st boyfriend. Not a good 2nd, and a horrible 4th. Jess was the bad boy. Good only for the rebellious period. Seriously, I laughed reading how he’s described because nobody talks about how Lorelai dislikes him and vise versa. How does that work out if he and Rory do get together? He treated both of them like dirt much of the time. Logan… he had his flaws, but was slowly becoming worthy of Rory. He went to Lorelai to ask for Rory’s hand. Would Jess do that? Anyway, I agree with your #1. 🙂 #2 would be Luke. Logan #3

  9. Tristan should’ve never gotten that high. Like he’s awful. I mean awful awful. I hate him. Remember the time he told Dean that he and Rory kissed at that party? AFTER Rory specifically asked him not to. What a dirtbag. He was so awful. I’d put him probably down there with Rune.

  10. #TeamDaveRygalski!!! Thank you for rating him so high, he’s always so unfairly underrated (which gets me peeved….) I think he is probably the best boyfriend of the bunch!

  11. I personally feel that Max should’ve been placed much higher. His whole storyline was basically derailed when the writer’s seemingly suddenly decided that Luke and Lorelei were going to be the couple standing at the end. In the beginning of the first season, we see Lorelei and Max break up because of the weirdness for Rory, despite their undeniable chemistry. Then, during their break, Lorelei has maybe a couple meaningful conversations with Luke and suddenly she’s smitten? It was all just a train wreck in the execution. Oh, and the interview scene…. That truly broke my heart. Don’t get me wrong, I love the Luke/Lorelei pairing in the later seasons, but I feel as if it were all executed poorly. Their entire early relationship was based off of comfortability. That’s not true love. I truly believe Max would’ve been the last one standing had he not been introduced in season one. He was underrated and under appreciated for what he was, someone who was crazy about both Lorelei and Rory. He truly wanted to be the man that they had never had in their lives.

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