It starts with a simple acoustic strum. Then, John Mayer delivers a line that basically guts anyone who has ever stared at a "delivered" text bubble for too long: "I should’ve left the party when I let you drive me home." It’s the opening of Sob Rock’s standout track, and honestly, the shouldn’t matter but it does lyrics are some of the most painfully relatable words he has ever put to paper.
We’ve all been there.
That specific, itchy kind of regret where you know, logically, that a relationship is dead. You know it’s over. You know you shouldn’t care who they are with or why they didn't call. But the brain and the heart are rarely on the same page. This song isn't just about a breakup; it’s about the lingering "what ifs" that haunt you at 2:00 AM when you’re supposedly "over it."
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Why the shouldn’t matter but it does lyrics feel like a punch to the gut
Mayer has always been a master of the "nice guy who messed up" trope, but here he leans into something much more universal: the weight of missed opportunities. The lyrics aren’t about a massive, cinematic explosion of a relationship. They are about the quiet, slow erosion of what could have been. When he sings about how they could’ve been "perfect together," he isn’t being hyperbolic. He’s being honest about the delusion we all carry after a loss.
Think about the bridge. It’s a masterclass in songwriting economy. He mentions how he should have "given you a Christmas present" or "checked in when your father died." These aren't abstract concepts. They are the tiny, mundane threads of a life shared that, when pulled, cause the whole tapestry to unravel. It’s the realization that being "right" or "cool" or "distant" cost him the very thing he wanted.
Most breakup songs focus on the pain of the person leaving. This one focuses on the self-inflicted wounds of the person who stayed too long—or didn't stay long enough. It’s a song for the people who are tired of pretending they don't care.
The Sob Rock aesthetic and why it works here
Released in 2021, Sob Rock was marketed with a heavy 80s gloss. Think pastel suits, Sheryl Crow vibes, and Yamaha DX7 synthesizers. But beneath the "yacht rock" veneer of the shouldn’t matter but it does lyrics, there is a raw folk core. It sounds like something that could have lived on Born and Raised, but the polished production makes the sadness feel more... modern? Maybe more sophisticated.
It’s easy to get lost in the 1980s soft-rock tropes. The gated reverb. The smooth guitar licks. But if you strip away the production, you're left with a diary entry. Mayer reportedly wrote this song (and much of the album) as a way to process a specific kind of loneliness that only hits in your 40s. It’s different than the angst of Room for Squares. It’s a "knowing" sadness.
Breaking down the most relatable stanzas
Let’s talk about the chorus. It’s the heart of the song. "It shouldn't matter, but it does."
That’s the whole thesis. It’s a confession. In a world of "ghosting" and "moving on" and "living your best life," admitting that something matters—especially when it shouldn't—is a radical act of vulnerability. He’s admitting he lost the breakup. He’s admitting he’s still keeping score.
And then there's the line about the "greatest love of all." It’s a cheeky nod to Whitney Houston, sure, but in this context, it’s incredibly cynical. He’s saying that if this was the big one, and he blew it, what does that say about the rest of his life? It’s dark. It’s heavy. It’s Mayer at his most self-deprecating.
- The Party: The opening scene sets the stage for a lapse in judgment. Letting an ex drive you home is a classic mistake.
- The Timeline: He talks about "four years" or "five." The ambiguity shows how time blurs when you're stuck in a loop of regret.
- The Other Person: He acknowledges they are with someone else now. The "shouldn't matter" part is his jealousy. The "but it does" part is the reality.
The technical brilliance of the arrangement
Musically, the song stays out of its own way. Don Was, the legendary producer who worked on the album, famously told Mayer to keep things "dry" and "real." You can hear the fingers sliding across the strings. This intimacy is vital. If the song was overproduced, the shouldn’t matter but it does lyrics would feel performative. Instead, they feel like a whispered secret.
The chord progression is standard folk-pop, but the phrasing is where Mayer shines. He lags behind the beat just enough to sound exhausted. Like he's tired of his own thoughts. It’s a technique used by jazz singers to convey emotion, and it works perfectly here to emphasize the "stuck" feeling of the lyrics.
What we get wrong about this song
A lot of people think this is a song about a specific celebrity ex. Was it about Katy Perry? Jennifer Aniston? Some girl from his high school?
Honestly? It doesn't matter.
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Fixating on the "who" misses the "what." The power of the song lies in its anonymity. If we knew exactly who it was about, we couldn't project our own regrets onto it. The song functions as a mirror. When you hear him talk about "the interface" of a phone or "the words you didn't say," you aren't thinking about John Mayer’s dating history. You’re thinking about that one person you still search for on Instagram even though you know you shouldn't.
The psychology of "Shouldn't Matter"
Psychologically, the song deals with "disenfranchised grief." This is the grief you feel for a loss that isn't "officially" recognized by society. If your spouse dies, everyone understands your pain. If you're sad about a "situationship" from three years ago that never quite got off the ground? People tell you to "get over it."
Mayer is giving a voice to that specific, illegitimate pain. He’s validating the fact that some things just stick to your ribs, no matter how much therapy you do or how many new people you date. It’s a heavy lift for a four-minute pop song, but he pulls it off.
Common misconceptions in the lyrics
Some fans debate the line "I'm a bad guy for many and a good man for few." Some see it as Mayer's commentary on his public reputation—the "bad boy" image he cultivated in the 2000s versus the person he actually is. Others see it as a direct apology to the subject of the song.
The truth is likely both. He’s acknowledging his polarizing nature. He knows he’s the villain in someone else's story. That self-awareness adds a layer of maturity to the track. He isn't playing the victim; he's playing the perpetrator who finally realized what he lost.
How to actually move on (According to the song's energy)
While the song is a bit of a downer, there is a path forward hidden in the notes. By admitting that it does matter, you stop the internal war. The stress doesn't come from the feelings; it comes from the resistance to the feelings.
- Accept the "But it does": Stop lying to yourself that you're fine.
- Stop the "What Ifs": The song is a warning of what happens when you live in a fictional past.
- Write it out: Mayer turned his regret into a hit song. You might just need a journal.
Practical Steps for the Heartbroken
If these lyrics are hitting too close to home, it’s time for a digital and emotional audit.
- Mute, don't block: Sometimes blocking feels too aggressive and triggers more regret. Muting allows you to disappear without the drama.
- Audit your "Party" moments: Like the opening line, identify your triggers. If seeing them at a specific spot leads to a "drive home" you'll regret, don't go.
- Listen to the full album: Sob Rock is a journey. This song is the low point, but tracks like "Till the Right One Comes" offer a bit more hope.
The shouldn’t matter but it does lyrics remain a staple of Mayer's live sets because they tap into a collective sigh. They represent the moment we stop pretending. In a world of filtered perfection, there is something incredibly refreshing about a guy with a guitar saying, "Yeah, I'm still sad about it, and it sucks."
Next time you hear it, don't just listen to the melody. Listen to the space between the words. That’s where the real story is.
To get the most out of this track, listen to the live acoustic versions available on YouTube. The lack of 80s production highlights the vulnerability in his voice, making the "it shouldn't matter" refrain feel even more desperate and honest. If you're analyzing the songwriting, pay attention to the rhyme scheme—it’s deceptively simple, which allows the emotional weight of the words to take center stage without being "too clever" for their own good.