From the album Manning Fireworks
This is a song about someone stuck watching their life shrink while their partner moves forward. Lenderman plays it slacker-loose, but underneath the jokes about Guitar Hero and staying home is a guy who knows he's already lost and can't do anything about it. The humor he says he lost? It's still there, just turned into a weapon against himself.
I've lost my sense of humor / I've lost my driving range
These aren't metaphors for depression. They're literal hobbies gone, small losses that add up to a personality disappearing. The driving range detail is perfect because it's so unheroic, so everyday middle-aged.
Don't move to New York City, babe / It's gonna change the way you dress
He frames it like he's giving wisdom, but really he's saying 'don't outgrow me.' The fear isn't about her clothes. It's that she'll become someone who wouldn't date him anymore.
I took off on a bender / You took off on a jet
Same verb, opposite directions. She's literally flying somewhere while he's just getting drunk in place. The rhyme makes it funny until you realize how mean it is to himself.
I've seen the Mona Lisa / I've never really left my room
Both things are true because one happened on a screen. He knows how pathetic this sounds. That's why he says it. Lenderman won't let himself off the hook even while he's making you laugh.
I've been up too late with Guitar Hero / Playing 'Bark at The Moon'
He's playing a video game version of someone else's rock song instead of writing his own. Except he IS writing his own, right now, about exactly this. That's the whole trick. He sees the trap he's in and stays there anyway.
The howl at the end could be Ozzy homage or just a guy alone making noise. Either way, it's the only moment he stops narrating his own failure and just lets something raw out. Then the song ends and presumably he goes back to the game.