‘Gilmore Girls’: Dean Wasn’t That Great

Disclaimer: this post is written from a very biased viewpoint. I’m #TeamJess but I want to be clear that I care way more about the actual Gilmore girls than any of their potential love interests. I just have a soft spot for a certain fake-tough, Walmart employee of the month. He’s not really the model boyfriend, either, don’t think I won’t acknowledge that. 

For a show produced in the early 2000s, Gilmore Girls managed to slide the word “feminism” in its pilot script. Yes, the term was kind of brought up as a joke, but I have no doubt in my mind that 16-year-old Lorelai Gilmore, rebellious and ready to run, really did name her newborn daughter after herself to stick it to that particular male-dominated tradition in the name of feminism.

Gilmore Girls, at its core, is about women who do exactly what they like when they like. They eat sugary foods all the time without shame, no matter who’s watching. Lorelai shirks off dating for 16 years because her daughter was more important to her than any man. Rory’s #1 priority is getting into Ivy League schools, a fact any citizen of Stars Hollow could tell you.

Of course, what’s a television show about women without romantic interests? Though I love to see Rory study, that makes for boring TV. Cue Dean Forrester, Chicago transplant and dimpled Romeo. Gasp, he’s tall! Gasp, he’s got a leather jacket! Gasp, he’s read a book!

It doesn’t take long before they’re dating and kissing on benches or causing a stir by accidentally sleeping over at Miss Patty’s.

The first clue to me that Dean was kind of the worst was his show-off with Tristan DeGrey at her dance (thanks, Chad Michael Murray, for proving that you CAN play someone with a more pretentious name than you already have).

Tristan has a crush on Rory, though she spotted his awfulness from a mile away and didn’t give him the time of day. Did Tristan push it too far? Absolutely. Was he the worst? Hell yeah. But Dean didn’t need to make a scene at Rory’s first Chilton school dance; she had it under control. Rory is barely assimilated into the school at this point, no one even knows who he is, and he’s fighting anyone who looks at Rory the wrong way. They weren’t even “boyfriend-girlfriend” at this point.

Though Dean didn’t take into account how this would affect Rory or what she wanted, she brushes it off, saying he “defended her honor.” As if any Gilmore girl needed someone to fight her battles.

This isn’t damning though; I still didn’t mind Dean until “That Damn Donna Reed,” an episode that irks me every time I come across it, and I suspect I’m not the only one. On a routine evening in the Gilmore household – TV and snacks, bless – the girls expose Dean to The Donna Reed Show, casually making fun of the ’50s values represented in the episode. Dean bristles. What if some women like to exist only to serve their husbands dinner every night?

The Gilmores rightfully laugh in his face. Real women aren’t like that, Dean, not even in the ’50s, despite what Donna would have you believe. Have you met a woman, dude? This fight doesn’t end there though, he goes on throughout the episode until Rory feels she should give in and make him dinner.

They break up a few episodes later because she doesn’t immediately reciprocate when he tells her he loves her, even though they’ve only been seeing each other for 3 months, she’s never been in a relationship before and he just sprung it on her.

They get back together of course, when she gives in once again and tells him she loves him. But the anger issues and jealousy start to blossom as GG moves into season 2. Rory and Tristan are assigned parts for Romeo and Juliet (a school assignment, and they both protested taking the roles.) Dean shows up to every rehearsal, even though Rory is uncomfortable with it. He’s not a big fan of trust.

Then, of course, Jess moves into town. Dean does not like Jess. (Lots of people don’t like Jess, which is fair. He’s prickly.) But Dean doesn’t like Jess because Jess is friends with Rory. Man? Friends with Rory? Not gonna work.

More than once Rory feels like she has to hide that she was hanging out with Jess (even with others around), because if Dean caught her, they would fight, which she outright admits.  Dean is still not a big fan of trust.

Then there’s the pushiness. Out of fear he’s losing her, Dean calls 14 times in a couple hours’ time in one episode. It’s no surprise she feels like she needs her distance. He pushes and pushes until their relationship ends in early season 3.

After the break up, Lorelai repeatedly tells Rory how good she had it with Dean, saying she had the best first boyfriend she could ask for. She says Rory was “spoiled” because she had a boyfriend who’d call her. He didn’t outright cheat on her and put up with her family, so I guess that makes him the best.

I won’t make excuses for Rory; she certainly makes mistakes throughout the series. When Dean later cheats on his wife with Rory, she’s not unaware he’s married. When Dean started to get territorial (ew) in season 3, she was totally crushing on Jess, even if she wasn’t aware of it. But Rory made it clear she had no ulterior motives when seeing Jess. Perhaps if he’d loosened up and made her feel like she was able to make her own decisions about how to spend her time, she would have chosen to be with Dean more.

For a show that was radical enough for having aired 16 years ago, I would have liked to have seen even one character call Dean out on his behavior. It’s not okay to make your girlfriend think she has to make excuses for being seen with another dude who she viewed as a friend. Gilmores do what they want, they don’t need to make excuses for it.

I’ll leave you with this, my succinct impression of Dean Forrester: Rory where are you? I haven’t seen you in hours, Rory. Have you looked at a man today Rory? Because if so, I swear to God, I’ll find him and kill him. You still going to Harvard, Rory? I feel insecure and have to take it out on anyone with testosterone. Why aren’t you answering my calls, Rory? RORY?

I know, it’s hard to believe I’m not Jared Padalecki.

A Note From The Writer: This show came out literally 16 years ago and has been on Netflix for over two. I don’t feel bad for spoiling.

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