Dean Forester Is Actually The Worst

Picture this: It’s 2013, summertime. You broke your ankle square-dancing on a slippery floor at camp and are laid up in bed for the indefinite future. No? Just me? Even so, every girl remembers where and when she first binged “Gilmore Girls.”

By Gwen Farrell3 min read
Gilmore-Girls-Rory-and-Dean screenrant
Warner Bros./Gilmore Girls

Maybe it was with your mom, sisters, or other female figures in your life. The colorful characters of Stars Hollow, CT made us laugh, cry, and yell in frustration all in equal measure at their exploits for seven endearing seasons (or if you’re of the same opinion as me, up until Rory went to Yale and became self-absorbed and unrelatable).

While it’s the women who were inarguably the focal point of the early aughts hit series, the men were pretty memorable as well. There’s Richard, the stern, dry-humored but unfailingly supportive grandfather. There’s Luke, the adorable if curmudgeonly diner-owner and one half of Lorelai’s slow-burning, will-they-or-won’t-they. There’s Jess Mariano — enough said. Then there’s Dean, Rory’s hometown crush and boyfriend who she begins a relationship with as she transitions from provincial Stars Hollow to the ivy-covered marble towers of Chilton Prep. 

I remember being that teenager with the broken ankle and thinking Dean got a bum deal. He was Rory’s first love, after all. But all these years later, a quarantine-induced rewatch has led me to the definitive conclusion that Dean Forester is actually the worst.

Red Flags Galore

Maybe Dean appeals to viewers because he reminds many of us of our own innocent crushes and first loves. He definitely recognizes Rory’s intelligence and respects her ambition and family dynamic, and though I wasn’t coming of age during the time GG was a primetime hit, I imagine the boy band hair, baggy clothes, and boyish grin also had a certain amount of appeal — but that’s about all we can say for the positives. 

From almost the beginning of their relationship, Dean love bombs Rory. For those who don’t know, love bombing is a popular tactic of abusive (usually narcissistic) people that relies heavily on manipulation. Love bombing is the practice of overwhelming someone with attention and adoration for a short, intense period of time, and then turning cold and showing their true selves once they don’t get what they’re really after.

Dean showers Rory with attention and plays well to her innocence and naivete. He fires back on her obscure pop-culture references, abruptly kisses her before they’re even dating, gives her a handmade bracelet, and is a frequent fixture at her house in the early days of their inexperienced relationship. Then, there’s the car.

When Young Love Goes Bad 

Here’s where we can pinpoint when Dean’s calculated tactics don’t go the way he planned: Season 1, Episode 16, “Star-Crossed Lovers and Other Strangers.” Dean and Rory get dressed up to celebrate their anniversary. He surprises her with a romantic, intimate dinner, and then gives her a car… 

Then he hits her with “I love you.” When you know without hesitation that you feel the same way, these can be the three most amazing words to hear. But it’s Rory. She’s thoughtful, cerebral, and likes to take time to think things over. She’s probably also overwhelmed due to the shower of gifts and attention she’s gotten from Dean thus far and is now backed into a corner. Also, she’s literally 16. It’s 100% okay that she doesn’t know if she feels the same way.

Not for Dean, however. He quickly turns from the sweet, giving, nice-guy-next-door into a cold, cruel and callous jerk. Rory even explains why it’s not that easy for her — her mom told her dad she loved him, and then he left. But for Dean who has invested time, money, and attention into her, Rory needing time to think and not immediately responding the same way isn’t good enough.

Being young and admiring the couples we see onscreen can be a powerful thing. We want what they have, whether it’s passion, a strong connection, an easygoing dynamic, or a whole other laundry list of characteristics.

Dean quickly turns from the sweet, giving, nice-guy-next-door to a cold, cruel and callous jerk. 

But when these examples turn out to be shadier than we realize, we need to ask ourselves what it is we’re really searching for. With every first relationship and high school sweetheart, falling quickly and deeply can be easy to do and take no time at all. Rory and Dean represent a cautionary tale on the sometimes unrestrained and unpredictable power young love has, and why it doesn’t always work out for the best.

What We Can Learn

While the love bombing factor is definitely something to watch out for, at heart Dean is an angry guy with an uncontrollable temper. He explodes at Tristan when Rory brings him to the Chilton dance, berates her on their anniversary leading to their first break up, and humiliates her in front of the whole town at the dance marathon. 

Although some fans think Dean’s downward spiral (he does take Rory’s virginity while being married to someone else, after all) is the result of a calculated character assassination by the writers to make other male characters seem more sympathetic, Dean wasn’t ever really that great to begin with. Sure, Jess is charming (and an infinitely more compatible match for Rory) and Logan is...well, rich, but Dean’s appeal is purely in being The High School Guy. 

Rory hadn’t had a chance to see a future and a life outside of Stars Hollow when they get together in season 1, and Mysterious New Cool Boy’s interest in her validates her awkward, shy demeanor.

At heart, Dean is an angry guy with an uncontrollable temper.

Having someone be attracted to you is a natural desire we all want. Being given gifts, attention, and flattery amid the excitement and newness of young love is a powerful, intoxicating feeling. But Rory learns — a little too late — that newness and attention aren’t all they’re cracked up to be. It’s when Dean tells her he loves her and she needs time to think that she sees the relationship for what it is — exciting and powerful, but also deeply unpredictable and uncertain. 

Closing Thoughts

It’s safe to say Rory wouldn’t have become the person she was without Dean (which isn’t entirely a good thing, given her attitude later in the series and in the revival). While first relationships can sometimes stand the test of time, with Rory and Dean there was always too much reliance on nostalgia.

First love is a magical, powerful thing, but when one person is uncertain about what they want and the other is an angry, manipulative jerk, the relationship isn’t necessarily meant to last forever.

There’s something endearing about first season Rory and Dean, with their hallway meet-cute and town square makeouts. But each was meant for different things, and the great thing about TV is we can fall in love and out of love with them any time we want to.