TV Boyfriend Smackdown: Dean vs. Jess vs. Logan from 'Gilmore Girls'

(The WB)

Welcome back to the TV Boyfriend Smackdown! We pit two (or three) of television’s most eligible — and fictional — bachelors against one another, and discuss their merits with regard to three major categories: attractiveness, personality, and potential for capital-D Drama. Based on our spirited debate, we’ll declare a winner, but fear not: you’ll have a chance to weigh in as well.

This week, we’re pairing up Jess, Dean, and Logan from Gilmore Girls. Beware of spoilers here — if we’re going to judge thoroughly, we’re going to judge on everything that’s happened so far and we can’t be held responsible for your inability to Hulu or Netflix in a timely manner (especially because Gilmore Girls ended in 2007). Let the smackdown begin!

Dean Forester
Lindsay's Take: Ugh, Dean. I fully admit I'm not a fan of Dean. He’s not going to win this if I have anything to say about it. Rory and Dean got together when she was in high school, and it was sweet for a while. Until, that is, she met Jess. But should Rory have held out for Dean to take her back?
  • Attractiveness: Dean is cute in an early-aughts kind of way. Floppy hair, kind smile, tall. Works at the grocery store. Whatever. He’s not the hottest guy in your high school class, but he’s the guy next door who is cute and friendly and wants to take you to the sock hop (coughcough*boring*coughcough).
  • Personality: Dean’s courtship of Rory was cute in the beginning, and then he went full-Fatal Attraction (well, okay, not really, but go with it) on her. He won’t be ignored, that Dean. He wanted commitment, and Rory just wasn’t ready. Rory finally came around, and then Dean was jealous of Jess. Oy. So far we have jealous and obsessed, folks. Then, when Rory N’ Dean Part Two: Stars Hollow Boogaloo came up, a married Dean (poor Lindsay) took Rory’s v-card, said he was leaving his wife, and then didn’t. Jealous, obsessed, cheater, liar. Need I say more?
  • Possible Drama: Dean needs to dial it back on all levels. He’s just too much: he was too into Rory, and then he was too jealous with Rory, and then he was too excited to take her virginity when he was married. He’s the Nice Guy who gets friendzoned and claims not to know why, but it’s really because he’s not that nice. Sorry, I’m not sorry.

Jess' Take:
  • Attractiveness: Sooooo turn-of-the-millennium cute. I mean, that hair wasn’t just floppy, it was like, floppy floppy. Dean definitely had the boy-next-door appeal, and if I were Lorelai, I’d trust him to take Rory out on the town based on wholesome looks alone. (Except maybe not after that time Rory and Dean fell asleep at Ms. Patty’s. Oops!)
  • Personality: I was into the leather jacket when Dean first appeared, but looking back, it didn’t him...and I mean both size-wise and personality-wise. Dean was pretty vanilla all the way, topped with a dose of cloying overbearing-ness. If Dean could’ve sliced Rory open and made a home inside her, I’m pretty sure he would have. Graphic and gory, but true. Boy was obsessed, jealous, and insecure. Not a great combo.
  • Possible Drama: Back away from the pretty blue-eyed girl, Dean. I get that Rory was his first love, but hot damn, Dean was way too into her. He obviously never really got over Rory (hello, cheating on his wife?) and it led to plenty o’drama. My advice? Do not engage.

Jess Mariano
Jess' Take: First and foremost: I solemnly swear that my love for Jess Mariano has nothing to do with our shared first name. I’m better than that, I promise you, Smackdown readers. Jess and Rory had a rocky start, found their groove after a while, and ended up friends...ish. So let’s assess!
  • Attractiveness: Of all Rory’s suitors, Jess was the best-looking. Period, end of sentence. That floppy hair, teasing smirk, eyebrows that meant business, and arms that somehow showed off how he could not only hold up a heavy hardcover novel but also rebuild a car engine. Yum. Jess wins in the looks category, for me.
  • Personality: Okay, fine, Jess had a bad attitude. I’ll admit that. He had authority issues, daddy issues, and his dogged pursuit of Rory (while amusing because it bugged Dean and Dean bugged me) got a little invasive at times. When a girl shoots you down, Jess, sometimes you gotta walk away. I get that Rory was kind of torn between him and Dean, but until she gave him some kind of legit signal of interest, getting in her business to that extent is not okay. Saving graces: Jess was extremely well-read, smart, eventually became a published author, and, most importantly, really did love Rory freakin’ Gilmore. 
  • Possible Drama: Jess is exactly the kind of guy who’s easy to fall for but hard to be with: a bad boy you think you can fix. His “bad” was more like “Stars Hollow bad," though. He never got into heroin or shot someone or did anything CRAY like that. Still, there was plenty of drama to go around when it came to Rory and Jess’ relationship: petty theft, a crashed car, random disappearances and reappearances, and never really being able to commit? All Jess’ fault, sadly. But I'd still date him.

Lindsay' Take:
  • Attractiveness: Jess is admittedly so much more of my type that the other guys. I always did like brooding, after all (hence the eternal love for Ryan Atwood). Dark, brooding, wearing a Mavi jean jacket (don’t front, you had one), always with a book in hand. Hot. Agree with Jess (my Jess). Hot.
  • Personality: Jess read a lot of Kerouac and Burroughs, which when you’re 16 means you’re cool and deep and introspective (when you’re 26, not as much). For all of his “I’m a badass” faults, Jess really always did care for Rory. He has a hard crunchy shell, but a gooey soft interior. After all, who was it that really pushed Rory to go back to school after she quit Yale? He yelled at her for putting up with playboy Logan’s shenanigans, he yelled at her for quitting school, and he showed her the novella he wrote. All of that inspired her to get her ass in gear and get back to it. #GetItGirl
  • Possible Drama: My Jess is right in saying that all of the relationship drama between Rory and GG Jess was his fault. Absolutely. But at the end of the series, he seems to really have his stuff together, so the chance for drama was way lower than it was at the beginning of the series. And who doesn’t love a reformed bad boy? I know I do.

Logan Huntzberger
Lindsay's Take: Ah, Logan. Rory’s project (more so than Jess ever was). Logan came to a post-losing-her-v-card-to-Dean (gross) Rory, who just thought she wanted to have casual sex with a dude from college. Well, they did, they “will-they-or-won’t-they”-ed, and they got together for good, with Logan proposing to Rory at the end of the series. She wasn’t ready (because she was, uh, 21), but should she have given Logan another chance?
  • Attractiveness: Sandy blond hair (though the style is so 2006). Soulful brown eyes. That confident smile. Logan is traditionally attractive, sure. He should dress better than he does given that he’s, uh, amazingly rich and the heir to a multimedia conglomerate, but I’ll chalk the half-zip sweaters and bootcut jeans up to the years (2005-2007) rather than the man.
  • Personality: The guy’s got charisma for days. Sure, he’s rich, which is also a benefit, but he’s got you in the palm of his hands with a wink and a smile. He had his moments of jerkdom (the break they went on, getting jealous about Jess, telling Lucy about Marty), but for the most part, Logan proved to be an attentive, loving, awesome dude to be with (see: the rocket, Richard Gilmore’s heart attack, etc.).
  • Possible Drama: Logan’s drama stems from a whole freight car full of daddy issues. It goes like this: he does something rebellious in order to break away from the Huntzberger name, he comes back down to Earth, he pisses off (or is pissed off by) his father, he does something rebellious… you get the idea. Rory was there to act as a source of gravity, but Logan always did have that chip on his shoulder. Make him go to therapy or take dad out of the picture to ensure a D-R-A-M-A-free relationship.

Jess' Take:
  • Attractiveness: A little too “Richie Rich” preppy for my tastes, but I recognize that Logan was objectively an attractive guy. And I don’t blame Rory for deciding to go for the blondie after her horrible track record with dark-haired boys. Change is good.
  • Personality: Sweet with a hefty dash of smarm, that’s how I describe Logan Huntzberger. One look at that smile and you just know he both resented and took advantage of his privileged upbringing. I’m down with confidence, but Logan’s sometimes had a little bit of an edge. However, I’ll agree with Lindsay that he was ultimately a nice guy and ended up being for real when it came to Rory.
  • Possible Drama: Aside from the chip on the shoulder Lindsay already mentioned, there was also the whole “I’ll propose to you in public even though we didn’t discuss this like, at all, and it will probably embarrass you beyond-beyond” thing. Kind of demonstrates a flair for the dramatic, no? I guess you could eventually work through it all with Logan, but it wouldn’t exactly be smooth sailing. More like, “Iceberg! Right ahead!” every few months.

Winner: Barack Obama

So why did we pick the 44th President of the United States? Well, because that’s who Rory picked in the end. At the end of the series, Rory declines Logan’s very public proposal to follow her heart and her journalism career as a press member on the soon-to-be President’s campaign trail. The other reason? We're so split on this (Jess loves Jess, Lindsay loves her some Logan), that we really just can’t choose. And a divided house cannot stand.

Be our tiebreaker, would you? Just vote for your preferred winner in this round of the TV Boyfriend Smackdown below, and we’ll see you in two weeks for our next match-up.

Poll: Dean, Jess, or Logan?
Click to vote:
  • Dean
  • Jess
  • Logan