• Gina Denny

Rory Gilmore’s Love Life

This is just a way for me to fully address this post by Forever Young Adult. And this one by Hello Giggles. My good friend M, who writes Teenagers are Ridiculous, sent me those links and said “Let’s discuss”.

After (no joke) a dozen facebook comments in five minutes, I realized I needed to blog about this. First I made a t-shirt stating that fact, and then I came over here.

Here’s how I see Rory Gilmore’s Love Life.

Dean Forrester: Season 1 – Early Season 3, then a fling in Early Season 5

PERKS – He’s cute (given the time, the small town-ness, and the abs he grows into eventually).

– He seems to really love Rory, right from the beginning. – He is sweet and Lorelai likes him.

– He respects Rory

– He makes stuff for Rory (more on this in a minute)

CONS – Rory forgets him very, very easily. The minute Jess is in the picture, she forgets that Dean is standing right next to her. There’s obviously not any real chemistry there if anything shiny and new distracts from his presence.

– He’s a little on the stalker-y side. Okay, not a little. A lot. When they first start dating, Dean admits “I watch you.” and then describes a very detailed account of what Rory does and what books she’s been reading. (I’ve been married for nine years, my husband does not know what book I’m currently reading)

– He becomes possessive on their first real date. At Rory’s school dance, he gets all territorial when Tristan speaks to Rory. Honestly, he might as well piss on her.

– The territorial jealousy gets worse and worse as the years go by. He punches Tristan, he punches Jess who is currently dating Rory, even though Dean is currently dating Lindsey. Seriously, he fights for his ex-girlfriend’s honor in front of his current girlfriend. He gets all nostril-flaring angry whenever he see Rory talking to someone who isn’t 1) Lorelai 2) Lane 3) him.

– He’s a dummy. He doesn’t like to read. He doesn’t do well in school. He can barely get into a state school and then drops out almost immediately. He’s just a big goofy meathead. Which is fine for some girls, but not for bookworm, aspires-to-be-a-political-journalist Rory.

– His life vision is totally out of whack with hers. He wants a housewife and a white picket fence. She wants none of those things. Sure, she plays dress up to please him in this department, but that’s a big red flag all on its own.

– He is a relationship MESS. He marries a girl whom he doesn’t love. Then, surprise! he cheats on her. And then does it again and again. Then he verbally abuses his wife and deliberately destroys his marriage. All bad signs. Hey, Rory, here’s a hint: You don’t want a guy like that.

– He makes her a freaking car. Most people put this in the “win” column, but I just can’t. They’d been dating for three months at this point. I don’t know how long it takes to build a car, but I’m betting that he was thinking “This relationship is forever” after… what?… a couple of weeks? Maybe before their first real date. YIKES.

To sum up: stalks her before they meet, plans on being with her forever from before they are a couple, becomes instantly territorial and jealous, doesn’t like the same things as her,  doesn’t notice and/or care that they want totally different things out of life. But, hey, he’s handsome. So he has that going for him. Jess Mariano: Technically only Season 3. But the tensions starts in Season 2 and resurfaces every time he does.

PERKS – He’s cute

– He’s smart

– He’s well-read (something that is far more important to Rory Gilmore than it would be to a lot of people)

– He’s quirky. He gets her sense of humor and music and movies without having to try.

– He’s an introvert (also much more important to Rory than most)

– Rory and Jess click.

– When he does get his head on straight, he comes back to her and asks her forgiveness. When she says no, he leaves. He respects her wishes, no matter how much it hurts him.

– He’s the one who convinced her to go back to Yale. Yes, Lorelai said her piece, but that didn’t budge Rory. Jess is the one who called her on her BS and convinced her to go back to Yale.

CONS – In the early years, he smokes. They don’t show this later, so I assume it’s a youthful “I desperately need attention” thing.

– He is an angry young man. Here’s where things get dicey for Jess. He is angry. He’s been abandoned by his father and ignored by his mother. The more he acts out, the worse things get, and Liz eventually kicks him out. By the time we meet him, he is hurt and confused and incapable of properly handling himself.

That doesn’t excuse his behavior, of course, but I also don’t think he’s nearly as bad as most people think he is. We spend so much time in Lorelai’s perspective, I think it colors everybody’s opinion.

Jess never forces himself on Rory. He makes a move with his serious girlfriend a few days after she basically said she wanted to have sex soon. When she says no, he backs off. Yes, he’s a jerk about it, but that’s not really about the sex, it’s about his personal problems and we all know it.

– He leaves without saying goodbye. Twice. Rory forgave him for the first one (and chased him to New York, by the way), so we all should too. That still leaves the second one, and that’s bad.

To sum up, he’s an angry kid who takes longer than most to get his head screwed on straight. Once he does, he’s golden.

Logan Huntzberger: Mid-Season 5 – Season 7

PERKS – He’s handsome (she’s old enough by this time to not be looking for “cute”)

– He’s fun

– He’s rich

– He’s connected and can help Rory be connected too

– He’s popular

– He’s exciting. He shows Rory the LDB and helps her (literally) take a leap

(quick sidebar: some of those are the shallowest reasons ever to be with a person and I felt a little skeezy typing them out)

CONS – He’s immature. Even at 23, he still acts 16. He thinks it’s hilarious and awesome that he got kicked out of prep schools, spends all night (literally) playing cards, interrupts Rory’s classes, shows off his money, etc. The list of immaturity gets tiring.

– He’s almost as territorial as Dean was, harassing Jess, despite the fact that he was anti-relationship when the whole thing started.

– He cheats on Rory. OR, if you buy into the whole “we were on a break” thing, then he left Rory’s bed and jumped immediately into the beds of a half dozen other girls. Either way, this is a scumbag move. I agree with Rachel’s handling of this situation over Rory’s.

– He doesn’t want to date Rory. So far as I can tell, he went along with it at first because it meant non-committal sex. He made it clear that he wanted no strings. The whole start of their relationship makes me a little nauseous because I feel like she has sex with him just to prove that she’s no goody-two-shoes, which is one of the worst reasons to have sex with a guy, right behind “to settle a bet” and “he forced me to”.

– He is the worst kind of influence. Under his tutelage, Rory goes from a two-beers-at-spring-break girl to a close-down-the-pub-every-night girl, drops out of Yale, commits a felony, moves into her grandparents’ pool house, proudly proclaims herself “the greatest slacker of all”, stops talking to her mother, and gives up on all her dreams entirely. I don’t care what camp you’re in: all of those are bad, bad, bad.

– He doesn’t know Rory at all. He proposes in front of her grandparents and a hundred semi-strangers. He attempts to steal from her grandmother. He wants to move her to San Francisco where she will hike, and mountain bike, and grow an avocado tree. He coddles her and treats her like a trophy wife instead of the independent female she wants to be.

– He never admits to being wrong, he twists Rory’s words around and gets her to agree to things that make her unhappy, he weasels out of every argument and disagreement.

To sum up, he’s fun and exciting but really offers absolutely nothing else positive.

Marty: Never dates Rory but is around from the beginning of Season 4 to the end.

M actually suggested Marty as a should-have-been-a-boyfriend, and I thought I’d address that issue here. Since he isn’t actually a boyfriend, there’s less to go on. But it’s an interesting idea.

PERKS – He’s funny

– He has Rory’s same sense of humor

– They click

– He is smart (he goes to Yale)

– He works for everything he has. He’s a scholarship student that works three jobs to make ends meet. He understands Rory’s life as the daughter of a struggling single mother in a way that most of their Yale colleagues cannot possibly comprehend.

– He’s kind and treats her well

– Late in season 7, we see that he’s still carrying a torch for her (more on this)


– He carries a torch for her. Some people think this is sweet, but it’s only sweet if he’s not dating other girls while he’s still in love with Rory.

– He’s background. He’s not even an introvert, he’s just uninteresting. Maybe this is the product of the writing, keeping him in the background, but it’s true anyway.

– He lies to his girlfriend. And in a really, really weird way. He pretends to not know Rory and keeps the sham up for months. When confronted, they have to break up because of the dishonesty (of the creepiness, not sure)

– He’s a doormat. He lets Logan treat him like dirt. He follows Rory around like a lapdog. He’s just… blah.

To sum up, there’s nothing really wrong with him, but there’s just not enough to go on. Maybe had Rory not been dazzled by Logan the Magnificent (as he likes to call himself, I’m sure) this might have been different.

In  my headcanon, Rory comes back from her tour with Obama, gets a job in DC, which is not terribly far from Jess in Philadelphia. They date long distance for a very short time before Jess moves to DC to be with Rory. They never officially marry, but stay together for the rest of forever and are happy now that everybody has their head on straight.


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