Gilmore Girls Fans: Are You Team Jess, Dean or Logan? (Exclusive)

In the summer of 1973, all I wanted to do was kiss boys. Cute boys, to be exact. Best of all: cute boys with sexy cars — Mustang convertibles, flirty MGs, souped-up Camaros. I was 16 years old and worked as a department store model at the Warwick Mall and that summer boys were everywhere. There were the Jordan Marsh stock boys, their muscles bulging beneath white T-shirts as they wheeled racks of men’s suits or wedding gowns through the store; there was the green-eyed boy who worked in the bookstore; the curly-haired boy who worked in the record store; the college boys in their summer jobs at the mall.

I was a good girl, meaning that all I did was kiss the boys. Not even second base as our bodies pressed together, the stick shift between us, the boy groaning with pleasure and frustration, his hand creeping up my shirt and down my cutoff jeans, me slapping it away. Such power I had that summer! And although I was a good girl, I was not a very nice one. One night, a college boy working in the shoe department took me to dinner at Valle’s Steak House. He picked me up in his father’s very unsexy Ford and wore a very unsexy brown suit. By the time I was cutting into my filet mignon, I was finished with him. My mind wandered. He ordered a second martini, I thought about the book waiting for me at home. I thought about the cute boy who was taking me to the movies the next night. I could see his heart breaking all the way through to the cheesecake, but I didn’t care.

Now, 50 years later, I care. The adult me worries constantly about hurting people’s feelings. I help people who are lost in my Greenwich Village neighborhood and make dinner for my students. I listen to my friends’ problems, even when deadlines are pounding on my door. But that 16-year-old me did not think twice about a teenage boy’s tender heart. I was tall and blond and tanned from spending long days on the beach slathered in Coppertone and eating root beer Popsicles, talking about boys with my friend Beth. My power felt so enormous that my nerves actually tingled with it. I walked around with an electric current shooting through my body, and that electricity drew boys to me.

One of those boys was a kid from school named Roland. He was skinny and he needed braces and he had acne. Maybe worst of all, Roland rode his bike everywhere. I would have ignored him completely, but he was my good friend, one of the small clique of smart kids who hung around together in a school where being smart was only considered an asset by the teachers. Roland and I laughed our way through chemistry class and sold candy bars in the cafeteria to raise money for the school. We often did group projects with our friends to ensure getting an A and ate pizza or doughnuts while we worked diligently at someone’s kitchen table.

That summer of 1973, Roland rode his bike to my house a lot. I’d come home from the beach, sand clinging to my suntan lotion, hair wet and my mother would tell me that Roland had come by. Again. “Just tell that poor boy you’re not interested,” she said. “We’re just friends,” I snapped. I’d come home from work only to find out that Roland had stopped by again. He always had iced tea with my mother when I wasn’t there, which made me mad at both of them. That he had pedaled his bike four and a half miles in 90-degree weather to “stop by” never occurred to me.

If I was home when he showed up, we sat on the back porch and talked about our summers. I see now that Roland actually did interesting things, like climbing Mount Washington and biking around Cape Cod, while all I did was stand in the Jordan Marsh window in autumn “school clothes” mannequin modeling, which meant not moving except once every two hours, lie on the beach with Beth and kiss boys. But back then, Roland seemed about as uncool as a person could be. Why would someone hike over 6,000 feet just for a view? Why bike around Cape Cod when you could drive? But since we were only friends, I listened and teased him that he was too pale and needed to go to the beach more.

Then, one day, driving down Route 2 on my way home from the beach, I saw the sign at the Warwick Musical Theatre announcing its upcoming shows. Engelbert Humperdinck, Tom Jones, Liberace and then, coming on July 21 for one night only: George Carlin. Anyone who came of age in the 1960s and ’70s adored George Carlin, could recite his Seven Words You Can Never Say on Television perfectly and quote the weather report he gave as the Hippy-Dippy Weatherman: “Weather tonight: dark. Turning partly light by morning.” George Carlin was one of the few cultural touchpoints I shared with my 5-years-older-than-me brother and my younger cousins. Everyone loved George Carlin.

From the minute I saw that sign, I made it a mission to get a cute boy with a sexy car to take me to the show. The red-haired boy who went to the fancy private school. The blond stock boy with eyes like Paul McCartney. The bookstore boy, the record store boy, the new boy who worked at Jordan Marsh in the linens department. I let them all know that I wanted to see George Carlin more than anything. Then the phone calls came, all with the same bad news: The show is completely sold out. I had my eyes set that week on the blond stock boy, so to him I persisted. “There has to be two tickets somewhere . . .” I complained to Roland one afternoon as he sat, sweaty from the long bike ride, guzzling lemonade. “Completely sold out? There are over 3,000 seats! How can it be sold out?”

And then, just days before the concert, a miracle. I was at home, sitting in front of the box fan in the living room, when the phone rang.

“I got two tickets!” a boy said. “To George Carlin!”

My excitement would have been even bigger if the boy had been anyone but Roland. But Roland it was, the procurer of the sought-after tickets.

“You want to go, right?” he said.

“Yes!” I did want to go, and if seeing George Carlin live and in person meant going with my pal, then so be it.

In my memory, the phone rang again minutes later, though it might have been the next night.

“I got two tickets!” a boy said. “To George Carlin!”

Not just a boy. The boy. The blond stock boy with Paul McCartney eyes.

“You want to go, right?” he said.

“Yes!”

“With me?” he said.

“Yes!”

Great, he would pick me up at six on Saturday night.

Lost in the joy of a date with the blond stock boy, it took a few minutes for my predicament to become clear to me.

My mother was sitting at the kitchen table, drinking black coffee and smoking Pall Malls, a game of solitaire spread out before her.

“Mom, you have to do me a favor,” I said.

She narrowed her eyes behind her bifocals. “What would that be?” she asked, cigarette between her lips, a four of hearts suspended in the air. My mother and I always got along just fine, but this summer I was pushing her patience. A lot.

“You have to call Roland and tell him I can’t go to George Carlin with him Saturday night.”

“Why can’t you go? All I’ve been hearing about for weeks is George Carlin.”

“Because that cute stock boy asked me to go!” I said, exasperated.

Mom put down her cigarette. “Do you honestly believe I’m going to call that poor kid and break his heart for you?”

“Yes!”

She leveled a cold gaze at me. “Ann,” she said, “I know you and I know that you will do the right thing in this situation.”

I stared back at her. She resumed her game of solitaire.

“Fine,” I said, and stomped into the living room, where I called Roland and told him that I had to work on Saturday night.

The PEOPLE Puzzler crossword is here! How quickly can you solve it? Play now!

Oh! The blond stock boy picked me up in his Pontiac Trans Am, muscles bulging beneath his baby blue shirt, hair curling just right over his collar. It was July in Rhode Island, hot and sticky and full of promise. He held my hand as we made our way through the crowd, showed our tickets to the usher, and led me into our row. Right beside Roland and his brother.

Roland looked at me and then he looked at the stock boy and he sunk deep into his seat. I do not remember if George Carlin said the seven dirty words or played the Hippy-Dippy Weatherman. I only remember wanting to disappear, to run out into that summer night and just keep running, maybe forever.

It comes as no surprise that Roland never spoke to me again, not even at our 25th high school reunion. He went away to college and became a doctor, whereas the stock boy still lives in his little hometown, where he has grown round and stagnant. I spotted him not long ago, sitting in a plastic-webbed lawn chair drinking a beer in front of the fire station.

By the time that summer ended, I’d had my heart broken by a college boy named Peter who worked in men’s wear. For the whole month of August, we went to the beach on our days off and made out in his charmille green Citroën. We ate cheeseburgers and ice cream sundaes, frozen lemonade and A&W root beer. He made me so dizzy I couldn’t even concentrate on Camelot, which was rereleased at the movies that summer, and struggled to discuss Guinevere’s fate with him afterward. But then Labor Day came and he went back to college and never called me again.

What does any of this — Roland, the stock boy, Peter and his Citroën — have to do with the television show Gilmore Girls or Logan Huntzberger and Rory Gilmore?

Well, everything.

After my second divorce (a story for another essay), I was about as crushed as a person can be. Twenty-five years, three children — and the loss of our second child, Grace, when she was just five — a home built in 1792 that I tended and nurtured all came crashing down in the ugliest ways possible (this, too, is for another essay). I was broke and broken. And forced to leave that sweet home of mine because I didn’t have the money to buy out my ex. At almost 60 years old, I had to borrow money from my mother and have her cosign the mortgage on a new home, which added to my enormous sense of failure.

My preteen daughter and I moved into a loft in a renovated factory across town, in a neighborhood that was far from gentrified. But it had enormous windows, loads of sunlight, high ceilings and a modern kitchen. In other words, it was the complete opposite of the home I’d left. Our first night there, we ate spaghetti carbonara, our plates balanced on unpacked boxes because we had no dining room table.

As mothers do, or try to do, I pointed out all of the wonderful new things in our lives. The high school she wanted to go to was literally next door! Our new neighbors were great! We were getting two kittens!

Gently, my daughter said, “I know just the thing we need.” She picked up the two television remotes that I had not yet figured out how to use, pressed some buttons, and continued, “It’s this show that I think we are going to love. I’ve only seen the first couple of episodes . . .”

And just like that, the TV screen filled with the faces of Lorelai and Rory Gilmore. When the opening song, “Where You Lead (I Will Follow),” played, we found ourselves singing along enthusiastically, pointing to each other and high-fiving, laughing and crying in our new home.

Every night, we ate our dinner on unpacked boxes and watched Gilmore Girls, each time belting out “Where You Lead (I Will Follow)” with Carole King. Some nights we only watched two episodes; sometimes we watched as many as five. Luckily for us, there are 153 episodes, enough to finally unpack all those boxes, get a dining room table and start high school. We watched Rory fall in love with Dean in high school, break up with him to go out with Jess, break up with Jess and go back with Dean, and meet Logan Huntzberger in college at Yale.

Every Gilmore Girls fan is on a team — either Team Dean, Team Jess or Team Logan. To me, Dean was the perfect high school boyfriend: adorable, sweet, adoring and a little jealous. Jess, Luke’s nephew who sweeps into town and turns everything upside down — including Rory — is that bad boy with a hot temper. He likes to kiss and scowl and pick fights. But Logan. Logan! Handsome. Rich. Smart. He offered Rory so much — exciting adventures, a new way of life, the opportunity to step away from everything she knew and see a different world.

When cub reporter Rory starts investigating the Life and Death Brigade, a secret society at Yale, Logan invites her to one of its events — glamping in the woods. The highlight of the weekend is dressing up in formal attire and jumping off a seven-foot platform while holding an umbrella. At first good girl Rory refuses, but Logan convinces her to do “something stupid, something bad for you.” And so she jumps. The Life and Death’s motto is, after all, In Omnia Paratus. Ready for anything.

“I hate him,” my daughter announced when Rory and Logan stole a boat in season 5, episode 21, “Blame Booze and Melville.”

“You hate Logan?” I asked, stunned.

“He just got her arrested!”

“No, no. She’s the one who wanted to steal the boat. He said, ‘It’s not ours to take.’ And she said, ‘Let’s go.’ ”

“They end up in jail!”

We stared at each other, each of us thinking, Who is this person?

“I hope we can both agree Dean is not right for her,” I finally said as a peace offering.

“Obviously.”

In college, I fell for one wrong guy after another, always because they were so damn cute. The one who looked like John Denver, so sweet and enamored of me? No interest. The one in my Shakespeare class who always walked with me out of Independence Hall, asking me what I thought of Hamlet, of Lear, of The Merchant of Venice? I talked animatedly until we hit the quad, then I focused on finding the darling, aloof boy who drove a 1950s Cadillac so he could break my heart. By college, I had somehow stopped being the heartbreaker and become the wounded one, so that after I graduated, I protected my heart, dating randomly and without enthusiasm.

It is fair to say that I dated my share of Deans — nice, dull guys who liked me too much — but mostly I dated Logans, those devilish men who took me for lavish dinners and smiled their beautiful smiles, who fell in love with me but couldn’t commit. My daughter was right, why did I think Logan was so perfect, not just for Rory but in general? Why was I still so won over by cute guys who drove nice cars? Hadn’t my ex-husband been that very type, rolling into my life in a vintage Mercedes with a dazzling grin?

At every opportunity I reminded my daughter about Jess’s flaws. How he lied to Luke about skipping school. How he lied about being in a fight with Dean. How he cruelly made out with someone else right in front of Rory. How he kisses Rory when she’s still going out with Dean.

But then, in season 6, episode 8, after Rory has dropped out of Yale, when she is living with her grandmother and still dating partying, drinking Logan, Jess shows up out of the blue and gives her a copy of the novel he has just published. They go out for a celebratory dinner, only to have Logan show up and act like a horse’s ass, putting down Jess and blabbering about himself. As we watch, flashes of so many dinner dates with so many boys crossed my mind, the fake smiles as I listened to them talk about their hockey games, their sailboats, God help me, their insurance business.

“This isn’t you,” Jess tells Rory when he walks out of the restaurant. “I know you.”

And then, just like in Gilmore Girls, I met my Jess. A writer who has sowed his oats, who loves me truly, who is cuter than Logan Huntzberger or any of those guys in my past. But unlike Rory, and thanks to my personal Rory, I don’t let him go. I keep him.

But I am still steadfastly Team Logan. I know that of course Jess is the right one for Rory, but I also know that Rory, and my daughter, and I, all of us need a Logan. We need to have our hearts broken, and to break hearts. We need to cry on our friend’s shoulder while we eat leftover Chinese food, and we need to sit, hot and uncomfortable, beside someone who loves us that we do not love. We need to jump into the unknown and then pull ourselves up, bruised and aching, and jump again.

Daughter: Be kinder than I was, but don’t hold on to something that was never maybe yours in the first place. Outgrow your Logans, hopefully faster than I did. And then one day you will be in Vermont on a sunny August afternoon, or in a crowded lecture hall with an autumn wind banging the windows, or sipping a bourbon at a zinc bar, and your Jess, the person who knows you, will call out to you. And if you are ready, you will hear him. In Omnia Paratus.

Reprinted from Life’s Short, Talk Fast: Fifteen Writers on Why We Can't Stop Watching Gilmore Girls edited by Ann Hood. Copyright © 2025 by Ann Hood. Used with permission of the publisher, W. W. Norton & Company, Inc. All rights reserved.

Life’s Short, Talk Fast: Fifteen Writers on Why We Can't Stop Watching Gilmore Girls edited by Ann Hood is available now, wherever books are sold.