Anyone who knows me knows that Gilmore Girls is my favorite TV show. I watched it for the first time in high school and have literally never stopped watching since then—it’s been on a constant loop in my house, whether I’m bingeing it on my own or rewatching it with loved ones. My love for all things Stars Hollow has even made its way into my day-to-day life: I have Gilmore Girls stickers on my phone case and my computer; I listen to themed playlists and recap podcasts; I’ve even made some of my closest friends because of a shared love of this show and its characters. But it’s more than a comfort show at this point. I’ve learned a lot from revisiting it as many times as I have—it feels like I pick up on something new every time, whether that’s a detail I might’ve missed in the background or noticing how my reactions to certain storylines have changed as I’ve gotten older.
As with any teen drama, there are plenty of love interests to go around, and that means that many viewers end up on a “team” when they pick a favorite. To me, picking Gilmore Girls “teams” has always seemed more diehard than most—if you were a fan of one, none of the others would ever come close. Now that I’m about as old as Rory when the show’s original run ended, I can see how each of her main love interests—Dean, Jess, and Logan—brought their own strengths to the table and had their own flaws. Ahead, I’m breaking down one positive lesson and one negative lesson that we can each take from Rory’s love interests.
Lessons from Dean
Date someone who makes you a priority
It might be hard for some Gilmore Girls fans to pick a favorite boyfriend, but Dean is most often the least favorite (for reasons we’ll get to later). But it shouldn’t go unmentioned that he truly cares for Rory, even if that affection becomes a little twisted later in their relationship. Dean makes an effort to get to know her family and gets along well with Lorelai. He also did things to make Rory happy, like taking her to school dances or escorting her to the cotillion, even if he personally thought they were dumb. Not being able to fit in with a significant other’s family isn’t a dealbreaker per se, but if family is important to you, it’s a good sign when your partner values that connection. Relationships are also about compromise, and I think it’s admirable that Dean was often able to put his own feelings aside and show Rory how much she meant to him. I want to be with someone who will do the same for me, and I want to be able to return the favor, too.
The nice guy isn’t always the good guy
Of course, the nice things I said above about Dean are pretty much the only nice things I can say about him, ever. He might’ve had a sweet relationship with Rory in the beginning and might’ve been “the best first boyfriend a mother could ask for,” as Lorelai puts it, but Dean only gets more and more toxic as the show goes on. He starts calling Rory constantly, tries to monopolize her free time, and, of course, cheats on his wife with her. I can cut Dean a little bit of slack for the clinginess because he was only 16, but there’s no way to make his affair with Rory sound better. I also want to acknowledge that Rory didn’t handle things well, either—she was controlling of Dean when they weren’t even together, and she definitely should’ve known that sleeping with a married man would have consequences. But at the end of the day, your first relationship is meant to teach you more about what to look for in future partners, and that includes paying attention to red flags.
Lessons from Jess
Your partner should want you to succeed
Jess might’ve been the “bad boy,” but he showed a lot of growth over his time on screen, and nowhere is that more obvious than in his relationship with Rory. After they broke up, Jess acted almost like a guide figure for her in the later seasons. When Rory was taking a break from school, he was the one who talked some sense into her—giving us the iconic “Why did you drop out of Yale?!” moment. He’s also the one who suggested that she write a book about her and her mom in the revival miniseries. He recognized Rory’s potential and believed in her goals, so when she wasn’t meeting them, he knew something was wrong. The fact that he could pick up on these things even when they weren’t together anymore makes it clear how much he cared about her. Your partner should support you as you’re working toward your goals, celebrate with you when you achieve them, and comfort you if you face any setbacks.
Chemistry isn’t the same thing as compatibility
Even if you aren’t a fan of Jess and Rory’s relationship, it’s hard to deny the chemistry that these two have. They have a lot of common interests—they both like to read and have similar tastes in movies and music—and things were clearly working out for them physically since we see them making out all over Stars Hollow. But in the end (at least, at first), Jess wasn’t ready to fully commit himself to being the partner that Rory deserved. In truth, he wasn’t ready to commit to anything. When you’re dating or in a relationship, you want to be with someone who does more than make you feel good. Do you both want the same things? Is the other person someone you can genuinely see yourself spending a long period of time with, maybe even the rest of your life? Are they mature enough to make a commitment? Sometimes, two people might have tons in common and get along really well, but they aren’t in the same place to make a relationship work long-term. And that’s OK! It doesn’t make whatever connection you have any less valuable.
Lessons from Logan
Find a partner who brings you out of your comfort zone
Let’s get this out of the way now: I’m a Team Logan girl. Out of Rory’s relationships, Logan was the most secure partner she had, and not just because he was her longest. Part of that security came from how Logan helped Rory come out of her shell more in college. Logan is the first person at Yale to get her to be more adventurous—which gave us another iconic quote, “People can live a hundred years without really living for a minute. You climb up there with me, it’s one less minute you haven’t lived.” Obviously, I have to clarify that there is a difference between leaving your comfort zone and being reckless… stealing yachts is not condoned here at The Everygirl. But on a smaller scale, I do think that Logan showed Rory that there was more to life than being in Stars Hollow with her books, and she was better off as a result. Breaking out of your comfort zone is just as important for personal growth as it is for strengthening a relationship. It’ll give you a chance to learn more about your partner, and trying new things will bring you closer together.
You should never feel like you have to change yourself so someone will like you more
As much as I might love Logan, there are several instances throughout his and Rory’s relationship where Rory felt pressure to act differently. From the start, Rory agreed to try something casual with him even though she’d always been a “girlfriend girl.” Logan’s family also didn’t approve of Rory as a potential partner, and when his dad told her he didn’t think she had what it took to be a good journalist, it sent her on a downward spiral. Even when Logan proposed to her at the end of the show, he gave her an ultimatum—he wanted her to just say yes, even though he knew she wanted to focus on her career. It’s one thing to try new things for yourself, but it’s another to do it because you want to be perceived a certain way. The right person for you will appreciate you for who you are and not ask you to be anything less than yourself.
