Happy Gilmore Girls Day!

Happy Gilmore Girls Day!

Okay, today I’m going to discuss a super important topic – Gilmore Girls. Yes, I know it’s not for everyone… but then if you’re not a Gilmore Girls fan why on earth would you click on this? So I’m going to safely assume I’m writing this to people who get it.

I’ve recently binge-watched the whole 7 seasons… though I peaked too early and finished it a few weeks ago, so I’ve been re-rewatching it. Which has given me A LOT of time to think about the BIG question of Gilmore Girls… *drum roll*.

The Dean, Jess or Logan debate.

This horrible thing has happened though while I was re-re-watching, as an adult rather than a teenager when the show first aired… I don’t really like any of them. I have to admit  I followed Lorelai’s story much more closely this time around and feel I relate SO MUCH more to her than Rory. Smart, driven, having her shit together…. I’m really really not anything like Rory. And where teenage me thought that Lorelai was being a total painful mother by immediately disliking all of her daughter’s boyfriends. I feel it’s justified. I wouldn’t like them much either.



Dean is the super nice guy. Isn’t he just the nicest? But nice is all he’s got going for him – he doesn’t really do anything else. He’s not particularly smart, or funny, or interesting…. And is he really that nice? When he tells Rory he loves her instead of giving her a minute to process HE BREAKS UP WITH HER! Who does that? Shitty entitled teenage boys, that’s who. (Been there, done that. Like that actually happened to me. As a teenager a boy told me he loved me, I was honest and told him that I think I could fall in love with him – so he dumped me. That’s what true love looks like, hey? Running off because she needs a minute to think! FFS!)

There are a series of other moments where Dean is pouty, passive aggressive, and even possessive of Rory – remember the whole calling her 14 times in a row thing? Yes at that point he was rightfully concerned she was falling for Jess BUT calling someone repeatedly and leaving constant messages is not endearing, it’s creepy AF. Then when they broke up he immediately married whats-her-name and then cheated with Rory. It’s a whole mess. I have no love for Dean at all. None. Sorry Dean. You’re the worst.



I really really want to like Jess. He’s sweet, charming, he does that smile and the eyes thing – AND fun fact Milo Ventimiglia was 24 when he played Jess, so I’m allowed to think he’s hot. It’s not at all creepy. Thank goodness for that. ANYHOW – yeah… Jess…. Oh Jess… it was over before it really even began. He spent SO LONG trying to win her away from Dean with his pretty eyes and books and knowledge of things, but then he almost immediately screwed it all up. He failed high school, lied about things, tried to pressure her into sex at a party, then got in a punch up with Dean and then left without saying goodbye. WHAT THE HELL JESS?!?! And then comes back like a year later thinking she’s still going to be just sitting around in love with him and begs her to run away with him.

But I like that he sorts himself out and does things with his life. I also like that he did all that without Rory. Inspired by her, but on his own. So all his success and drive came from him. So I like him as a person, just not necessarily for Rory.



I have so many mixed feelings with Logan. Okay, no, here it is. I think Logan is wrong for Rory. I think he’s perfect for me, but terrible for her. The idea of Rory ending up with Logan in the end seems so wrong. Yes, my heart shattered when she turned down his proposal, but I just don’t feel it for them. Partly because it just seems so wrong her ending up with someone that her grandparents not only approve of, but that she’s actually several rungs down the upper class social ladder. It’s just too weird.  

He’s not terrible, yes he cheated on her, but he didn’t know they were still together – okay, fair enough. But even though he matures a bit, starts to take responsibility and all that good stuff. The big question I have for him as a long term partner for Rory is do we see him one day moving to Stars Hollow with her? Because while Rory will travel and be a world famous reporter – I see her ending up back in Stars Hollow. But I just can’t imagine Logan there. Getting coffee everyday at Luke’s diner, and going to town meetings, and participating in 37 different annual festivals.

I feel like one day Rory will want to go home, and I don’t see Logan going with her. So, he’s a no from me.

So, what’s the solution?


Or someone new. It’s been 10 years. SURELY she could have met another man in the last 10 years that is actually better suited to her. She doesn’t just have to choose between her 3 exes. They’re all exes for a reason.

But, I guess if I had to choose for her it’d be Jess. I think grown up Jess would be the best choice for her.

Who’s watching Gilmore Girls today? Who was your favourite of her boyfriends?

Rachel Stewart

Rachel is the founder of Parenting Central. She is raising two children, boy and girl, with her partner. Rachel is obsessed prams, car seats, carriers and all things baby. She has worked in the baby industry for several years, for both suppliers and also in a retail setting and has developed a passion for connecting parents with the right products to make their lives easier. When Rachel isn't playing with prams she's enjoys crocheting, drinking coffee (sometimes wine) and spending a little too much time on Facebook.


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