The pilot of Awkward didn't just introduce a show; it launched one of the most polarizing, frustrating, and strangely realistic toxic-ish relationships in MTV history. Honestly, it was a mess. Jenna Hamilton and Matty McKibben weren't just a TV couple. They were the personification of that specific high school purgatory where you’re dating someone who is simultaneously your best friend and your biggest source of insecurity.
When Matty first asked Jenna "to go" in that supply closet, it wasn't romantic. It was transactional. Jenna was the girl who survived a freak accident that everyone thought was a suicide attempt, and Matty was the popular soccer star with a six-pack and a serious case of public-image anxiety. He liked her. He just didn't like her enough to be seen with her.
That dynamic set the stage for five seasons of back-and-forth that fans are still arguing about on Reddit today.
The Secret Relationship That Ruined Everything
For most of the first season, Matty McKibben was, frankly, a bit of a jerk. He kept Jenna in the shadows. He’d sneak into her bedroom at night but ignore her in the hallways of Palos Verdes High. It’s a trope we’ve seen a thousand times, but Awkward creator Lauren Iungerich wrote it with a sharp, cynical edge that made it feel raw. Jenna wasn't just some pining wallflower; she was documenting her own humiliation on a blog, analyzing her worth through the lens of a guy who wouldn't hold her hand in public.
Then Jake Rosati entered the picture.
Jake was the "good guy." He was Matty's best friend, but he actually looked Jenna in the eye. This created the show's primary engine: the love triangle. But unlike The Vampire Diaries or Twilight, the stakes here weren't life and death. They were social death. When Matty finally realized he was losing Jenna to Jake, he had his "epiphany." He tried to change. He wanted to be public. But by then, the damage to Jenna’s psyche—and the audience’s trust in him—was already done.
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Why Jenna and Matty Never Quite "Fit"
If you look at the middle seasons, specifically Season 3, the cracks become impossible to ignore. This is usually where fans start to split. You have the "Team Matty" die-hards who believe their chemistry was undeniable, and then you have the people who realized that Jenna and Matty were actually terrible for each other’s personal growth.
Jenna Hamilton was a writer. She was introspective, neurotic, and deeply analytical. Matty was... not. He was a guy who communicated through physical touch and soccer metaphors. They spoke different languages. When Jenna got into her head—which was constantly—Matty didn't have the emotional vocabulary to meet her there.
There's this specific scene in Season 3 where Jenna cheats on Matty with Collin, the "intellectual" guy from her creative writing class. It was a turning point for the series. It was also the moment Jenna became a "villain" in the eyes of many viewers. But if you look closer, her cheating wasn't really about Collin. It was about her feeling suffocated by a relationship with Matty that lacked intellectual depth. She was bored. She was also self-sabotaging because she didn't know how to handle a "stable" version of Matty McKibben.
The Problem With the Time Jump
Season 4 and 5 are where things get weird. The show underwent a showrunner change after Season 3, and the tone shifted. It became broader, more slapstick, and arguably less grounded. But the core obsession remained: getting Jenna and Matty back together.
By the time the show reached the college time jump in the final season, the "will-they-won't-they" felt exhausted. Jenna was at a small liberal arts college in Maine (Idea University), and Matty was playing soccer at Berkeley. They had evolved into completely different people. Yet, the narrative gravity kept pulling them back to Palos Verdes.
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The finale is still a huge point of contention. Ashley Rickards and Beau Mirchoff had incredible chemistry, but by the final episode, the relationship felt like a habit rather than a choice. Matty shows up at Jenna’s camp, professing his love yet again. It’s meant to be this grand, sweeping moment. In reality, it felt like two people who were afraid to move on from their high school identities.
Jenna's Growth vs. The Matty Gravity
The truth is, Jenna Hamilton was at her best when she wasn't defined by a guy. Her relationship with her mother, Lacey, was arguably the most important one in the show. Her friendship with Tamara (played by the brilliant Jillian Rose Reed) provided more emotional support than Matty ever could.
When we look back at the show now, Matty McKibben represents a specific type of first love: the one that teaches you what you don't want. He taught her that being liked in secret isn't being liked at all. He taught her that you can't "fix" someone into being the partner you need.
Despite all the drama, the show succeeded because it didn't sugarcoat how messy these things are. Most high school sweethearts don't end up together. They shouldn't. They grow out of each other. Awkward tried to have it both ways—giving us the "endgame" while showing us exactly why it probably wouldn't last six months past the credits.
Key Takeaways for Rewatching the Chaos
If you're diving back into the series or just caught a clip on TikTok that sent you down a rabbit hole, keep these things in mind:
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- Season 1 is the peak. The stakes feel the most real here because the power imbalance between Matty and Jenna is at its highest.
- The "Letter" is the real catalyst. Everything Jenna does stems from that cruel "You're Welcome" letter. It's the ghost that haunts her relationship with Matty until the very end.
- Watch the background. The show was famous for its fast-paced dialogue and "Matty-isms." Beau Mirchoff played the "lovable dummy" role perfectly, which often masked how truly poorly Matty treated Jenna in the beginning.
- Tamara is the MVP. Seriously. If you're watching for the romance, you're missing the best part of the show, which is the banter between the best friends.
The legacy of Jenna and Matty isn't one of a perfect romance. It’s a case study in how our first major crush can fundamentally reshape our identity, for better or worse. It was awkward. It was painful. And honestly, that was the whole point.
To truly understand the impact of the show, look at how it handled the aftermath of their breakups rather than the reunions. The episodes where Jenna is forced to find her own voice—without Matty’s validation—are the ones that actually aged well. If you're looking for a roadmap on how to navigate a relationship that feels like a roller coaster, Awkward serves as a great "what not to do" guide.
The best way to appreciate the story now is to accept that their "happily ever after" was likely just another chapter in a long, complicated book of growing up. They were each other's "firsts," but they were never meant to be each other's "long-terms." And that’s okay.
Next Steps for Fans:
- Re-watch the Season 2 Finale: This is arguably the height of the series and features the most "honest" version of their dynamic before the writing shifted in later seasons.
- Analyze the "Carefrontation" Letter: Re-reading the text of the letter from Season 1 (which was actually written by Jenna's mom) provides a massive amount of context for why Jenna felt she had to change for Matty.
- Check out the Cast's Current Work: Both Ashley Rickards and Beau Mirchoff have moved on to very different projects, and seeing them outside the "Jenna and Matty" bubble helps put the show's intense fandom into perspective.