Is Conrad Fisher Gen Z’s Jess Mariano?

Everyone and their mother knows that fall is the perfect time to start their annual Gilmore Girls rewatch. As the leaves start changing and the temperatures drop, Stars Hollow just feels so much cozier. The only difference this year is that we’re still not over our summer obsession, The Summer I Turned Pretty.

Even if you’ve never watched an episode of TSITP (you’re missing out, btw), you probably know that the internet is obsessed, and that everyone is rooting for Conrad (Christopher Briney) to win Belly’s (Lola Tung) heart over his brother, Jeremiah (Gavin Casalegno). Conrad is the brooding and mysterious bad boy with a good heart, similar to Gilmore Girls fan favorite Jess Mariano (Milo Ventimiglia). As the show has gone on, many have spotted the similarities between the two characters, leading us to wonder if TSITP’s Conrad Fisher is Gen Z’s answer to Jess Mariano.

Before comparing the two iconic characters, it’s time for a brief overview of both.

Jess Mariano: The Bad Boy With The Heart of Gold

Every Gilmore Girls fan has a favorite of Rory’s (Alexis Bledel) boyfriends, and it’s no surprise that Jess is the fan favorite. When fans are first introduced to Jess in season two as Luke’s (Scott Patterson) rebellious yet handsome nephew, Rory is still dating Dean (Jared Padalecki), but Jess intrigues her instantly. He’s the epitome of the bad boy archetype and doesn’t fit in anywhere at Stars Hollow, but Rory can tell there’s something soft behind his tough exterior.

As Rory and Jess get to know each other, they learn they have a lot in common through their mutual love of literature, and she realizes that something is missing in her relationship with Dean. They have little to nothing in common, and their passion for each other wanes as Rory focuses more on her studies. While she tries to suppress her growing feelings for Jess, she has no choice but to face them when she and Dean break up in season three.

Rory and Jess start dating in the next episode, and their relationship is beautiful yet chaotic. They clearly care about each other and their relationship is deeply passionate, but it’s also full of conflict. They break up at the end of the season, leaving fans devastated.

Jess makes two appearances in the fourth season, one where he confesses his love to Rory, but they don’t get together, and later when he asks her to move to New York with him and she turns him down. He’s absent from season five, but the reason why so many fans love Jess is an appearance he makes in season six.

A more mature, put-together Jess returns and reveals he’s written a novel—one Rory inspired. He later tags along with Rory and her boyfriend, Logan (Matt Czuchry), whose smug behavior prompts Jess to walk out. What follows is one of the series’ most indelible scenes: Jess calls Rory out for how much she’s changed and urges her to really look at herself. The moment proves he’s finally become the man she once hoped he could be, and it helps push Rory toward reconciling with her mother.

He makes a few more appearances in the original run, but it’s his return in the 2016 Netflix revival, Gilmore Girls: A Year in the Life, that resonates most. He reconnects with Rory and urges her to write a book—proof he still believes in her after all these years. They don’t end up together, but it’s clear he still has feelings, and they’re the quintessential right-person-wrong-time pair. Had they met as adults instead of impulsive teenagers, there’s a good chance it would have worked.

Conrad Fisher: The Brooding Old Soul

Even before fans meet Conrad in season one, it’s clear that Belly has had a crush on Conrad since she was a little girl. He has the bad boy with the heart of gold type of swagger that could make any girl weak in the knees, and Belly hopes that he’ll finally notice her now that she has blossomed into a young woman. Unfortunately, her hopes are dashed when she arrives at the beach house to find Conrad cold and aloof. It’s later revealed that Conrad discovered that his mother’s cancer had just returned, and he’s struggling to cope with the news and the stress of hiding what he knows from his family.

While Conrad struggles with both depression and panic attacks throughout the first season, he shows his soft side to Belly by always being there for her and showing he cares for her in small but meaningful ways, like gifting her an infinity necklace. When his brother, Jeremiah, disappears the night of the debutante ball (fans later learn he had heard of his mother’s cancer that night), Conrad sweeps in to save the day, and the two get together at the end of the season, leaving Jeremiah heartbroken.

At the start of season two, it’s revealed that Conrad and Jeremiah’s mother died of cancer and that Belly and Conrad have since broken up. Through flashbacks, fans learn that while Belly and Conrad had a loving and passionate relationship, Conrad started pushing her away as his mother got worse. This led to them breaking up at prom because he couldn’t be present for her, and Belly made a scene at the funeral when she saw Conrad’s ex-girlfriend comforting him while he was having a panic attack. 

Fast forward several weeks, and Jeremiah calls Belly to tell her Conrad is missing. While things are awkward between Belly and Jeremiah, they grow close over that summer, and the two start dating at the end of the season. Conrad still has feelings for Belly, but recognizes that he’s not in a place to love her, and he reluctantly accepts that Jeremiah and Belly are together.

Season three begins three years later as Belly is finishing her junior year of college, Jeremiah is finishing his senior year, and Conrad is finishing his first year of medical school at Stanford. Conrad has barely seen Belly since she and Jeremiah started dating, leading Conrad to focus on school and work on his mental health through seeing a therapist. On the contrary, Jeremiah hasn’t grown up at all, leading him to repeat another semester of college because he was too focused on partying to check the requirements for his major. His relationship with Belly appears to be solid, but she’s annoyed with his constant partying and wishes he would start taking things more seriously. 

While attending a frat party, Belly overhears girls gossiping about Jeremiah sleeping with another girl during spring break, leading Belly to storm off and break up with him after he confirms the rumor. They only get back together when he’s there for her after her brother, Steven, gets into a car accident, and Jeremiah impulsively proposes to her.

They decide to get married at the end of the summer, leading Belly to get into a fight with her mom and move into the old summer house, where Conrad is staying. As Jeremiah works at an internship in Boston, Belly and Conrad reconnect, leading to a heartfelt love confession from Conrad.

Long story short, Conrad wishes Belly and Jeremiah the best before Jeremiah ultimately calls off the wedding when Belly admits that she’ll always love Conrad. As she packs her things, Belly uses the travel voucher her mother gifted her at her bridal shower to fly to Paris, only to see Conrad at the airport. She almost says hello to Conrad, but changes her mind when she realizes she might miss her flight. The fate of the characters will be revealed in the final episodes.

The Rise of the Black Cat Boyfriend

It’s crystal clear that Jess and Conrad have a lot in common. Both had a hard time communicating and expressing their emotions as teenagers, but show immense growth and emotional maturity as adults. They both recognize the mistakes they’ve made and are committed to becoming better men, but still secretly yearn for the girls, now women, they loved as teenagers. 

Both are self-aware enough to know that the women they love deserve better, and they put in the work to become better men. What makes this special is that love is not their only motivation, for it also helps them excel in their careers (Jess as a writer and Conrad as an aspiring doctor), allowing them to thrive on every level to become the best version of themselves. Both are heartbroken when they see the women they love fall for a guy who clearly isn’t good enough for them, leading Conrad to essentially recreate Jess’s famous “why did you drop out of Yale?” speech.

Jess and Conrad are perfect examples of social media’s favorite new type of boyfriend, the black cat boyfriend. Cosmopolitan India defines the black cat boyfriend as, “The quiet, complicated guy who’d rather die than make a grand romantic gesture but feels everything with disarming intensity. Unlike the golden retriever boyfriend, who is sunny, affectionate, and unabashedly obsessed with his partner, the black cat boyfriend doesn’t wear his heart on his sleeve. He’s slow to trust, fiercely independent, emotionally intense, and often misunderstood. He may come off as detached or standoffish, but under the surface, he’s deeply loyal, protective, and full of feeling.”

Fans call the “black cat boyfriend” the foil to the golden retriever: darker, pricklier, but ultimately devoted—and both Rory and Belly start with golden retrievers that viewers love to hate.

Before Jess, Rory dates Dean, who initially reads as the perfect first boyfriend: polite, attentive, endlessly doting. But the cracks show fast: they share little, he has no interest in her world, and he sulks at the first sign of friction. Jess, messy as he was, put in more effort and, crucially, grew after their breakup. Dean, meanwhile, regressed, cheating on his wife with Rory—proof the nice-guy veneer didn’t age well.

In the first two seasons of TSITP, Jeremiah seems like a wonderful guy. His only red flag seems to be the jealousy he shows towards Conrad and Belly’s relationship, which is understandable. Unfortunately, this doesn’t change as he gets older. Despite dating Belly for several years, he’s still threatened by the very thought of Belly and Conrad spending time together. Belly is also annoyed with his inability to grow up, and the way he cheats on her at the first sign of struggle in the relationship speaks volumes. Like Jess, Conrad isn’t perfect, but Conrad outshines Jeremiah in his ability to recognize he has to change and grow as a person for both himself and others around him.

This doesn’t mean all golden retriever boyfriends are bad (look at Travis Kelce) and that all black cat boyfriends are good. The overall consensus seems to be that black cat boyfriends provide a relationship with more depth and romance while providing the masculine bad-boy edge that so many of us crave in relationships.

Women Are Craving Romance, Yearning, and Masculinity In Relationships

The best endorsement for Belly and Conrad comes from Belly’s brother, Steven (Sean Kaufman), during the second season’s finale. In a discussion with Belly’s best friend, Steven says he prefers Conrad for Belly because he challenges her to be a better person. Sure, it’s simple, but it’s the perfect sign of a deeper relationship than the one she has with Jeremiah. Similarly, one of the best things about Jess and Rory’s relationship is how he constantly pushes her to be a better person. 

It sounds counterintuitive: both Jess and Conrad struggle to say what they feel, yet they’re die-hard romantics. They ache for the women they love, and they show it. In a dating culture that hands out gold stars for the bare minimum (he picked up the check! he walked on the curb side!), chivalry shouldn’t be a plot twist; it should be the baseline. That rock-bottom bar breeds situationships and flings where too many women settle for crumbs.

Jess and Conrad refuse crumbs-as-courtship. They go beyond the minimum without losing their edge—masculine, vulnerable, and committed to growth. They mess up, own it, and get better. That blend of romance, self-respect, and emotional intelligence isn’t just refreshing; it’s downright irresistible.

They also play into the age-old trope of taming the bad boy while simultaneously subverting it. Yes, they start as tortured rebels, but the real shift comes from their own agency: they choose to grow. Rory and Belly may be catalysts, not carpenters—they inspire change; they don’t do the emotional labor of remaking them. And when love doesn’t swing their way, Jess and Conrad don’t act entitled; they love enough to step back and let the women choose, even when it aches.