Honestly, it’s been a while since a rom-com felt as cozy as a warm blanket on a rainy Tuesday, but Gloria Calderón Kellett managed it. Then, Amazon went and pulled the rug out from under us. If you’ve spent any time scrolling through Prime Video lately, you’ve probably noticed the Diaz family is conspicuously missing a third chapter.
With Love Season 2 dropped in June 2023, and by November of that same year, it was officially canceled.
It hurts. It really does. Especially because the second season wasn't just a repeat of the first; it actually took some massive swings with the characters that left us hanging. We didn't just get more holidays; we got a deeper, messier look at what happens after the "happily ever after" usually ends in most shows.
The Messy Reality of Lily’s Love Triangle
Most people think rom-coms are just about the chase. You know the drill: girl meets two guys, girl picks the "wrong" one, realizes it at a wedding, and runs through an airport. But season 2 of With Love kinda flipped that.
Lily Diaz, played by Emeraude Toubia, was arguably at her most frustrating this season. And that’s a compliment to the writing. She was stuck between Santiago (Rome Flynn) and Nick (Desmond Chiam). On paper, Santiago is the soulmate—the guy who challenges her. Nick is the "easy" choice—the best friend who has always been there.
The season finale, "The Wedding," finally forced her to choose. But it wasn't a choice about a man; it was a choice about her own growth.
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Lily has spent her whole life obsessed with the idea of a wedding. She’s the girl who has had her Pinterest board ready since she was twelve. Watching her realize that a wedding isn't a personality trait was the real arc of the season. When she finally leaned into Nick, it felt like a pivot toward stability rather than the constant, exhausting fireworks she had with Santiago.
Jorge and Henry: The Anchors
While Lily was spiraling, her brother Jorge (Mark Indelicato) and Henry (Vincent Rodriguez III) were providing the emotional heavy lifting.
If you're a fan of Ugly Betty, seeing Indelicato play a fully realized, adult gay man who is allowed to be high-maintenance and vulnerable is just... chef’s kiss. Their relationship in season 2 dealt with some real-world friction. It wasn't just about being "out" anymore; it was about merging two lives that have very different ideas of what a home looks like.
We saw them grapple with:
- Perfectionism: Jorge’s need for everything to be "just right" for the family.
- Independence: Henry trying to find his footing within the loud, beautiful chaos of the Diaz clan.
- Commitment: Moving past the "new relationship" smell and into the "who left the dishes in the sink" phase.
It was grounded. It felt like something you’d actually talk about with your friends over mimosas.
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Why Amazon Canceled It (And Why They Were Wrong)
Business is business, I guess. In November 2023, the news broke that With Love wouldn't be returning for a third season.
The industry term is "cost-plus," basically meaning the show wasn't hitting the massive, global numbers that The Boys or Rings of Power pull in. But that's a narrow way to look at success. Gloria Calderón Kellett—the genius behind the One Day at a Time reboot—built something specific here. She built a show where Latinx characters weren't just the sidekicks or the "struggle" narrative.
They were just... people. Falling in love. Eating too much at Thanksgiving. Arguing about who the favorite grandchild is.
The show filled a void. It was one of the few places on TV where you could see a multi-generational, Afro-Latino, and queer-inclusive family that was fundamentally happy. In a landscape of "prestige TV" that’s usually dark and gritty, With Love was unapologetically bright.
The Unanswered Questions
The cancellation leaves a lot of loose ends that still bug me.
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What about Sol and Miles? Their relationship was one of the most progressive portrayals of a non-binary character in a romantic lead role we’ve ever seen. Sol (Isis King) and Miles (Todd Grinnell) had a chemistry that felt lived-in. We needed to see them navigate the long-term stuff.
And then there's the matriarch and patriarch, Beatriz and Jorge Sr. Season 1 saw them dealing with an affair and the near-collapse of their marriage. Season 2 was about the slow, painful work of rebuilding. We don't get to see the "happily ever after" for them either. We just have to assume they made it.
Actionable Steps for Fans
If you're still mourning the loss of the Diaz family, there are a few things you can actually do rather than just shouting into the void of Twitter (or X, whatever).
- Rewatch on Prime: Amazon, like all streamers, looks at completion rates. If you haven't finished season 2, do it. If you have, leave a positive review. Internal metrics matter more than social media noise.
- Follow GloNation: Gloria Calderón Kellett has an overall deal with Amazon Studios. Even though With Love is done, she has other projects in the pipeline. Supporting her new work is the best way to ensure we get more stories like this.
- Check out the Cast’s New Projects: Emeraude Toubia and Mark Indelicato are constantly working. Following their careers helps prove that there is a dedicated audience for the talent that made this show special.
The reality is that With Love Season 2 was a rare gem. It didn't try to be "The Great American Novel" of television. It just tried to be a good friend. While we might not get a season 3, the twelve episodes we do have are a masterclass in how to write joy without it feeling cheesy.
To get the most out of your rewatch, pay attention to the background details in the Diaz house. The production design is packed with "Easter eggs" of Latinx culture—from the specific brands of crackers on the table to the photos on the walls—that make the world feel entirely real. Supporting creators like Kellett is how we get more of that authenticity in the future.