I've added Rusty James and Oh Love to my list of favorites now, too.
rofl This is always how I go about doing albums. I'll start with one or two songs, then add, then add, then add, maybe subtract a couple when I start getting sick of them, add a couple more, subtract, and add until I've had a phase with every song, then eventually I pick out my favorites. Sometimes they're ones that were originally the ones I couldn't stop listening to, sometimes they're ones I didn't fully appreciate until I picked up on the intricacies of them.
Hmm. I would guess it's just about teenage relationships and how overdramatic they can be? "Stab my heart like a stick in the mud, cut my chest just to see the blood, now I'm singing out the alphabet as the tears are putting out my cigarette." The lyrics sound like they should be on 1039/SOSH, akin to At The Library, Paper Lanterns, The Judge's Daughter, etc. I don't necessarily think it's a personal song, unless it's reflecting on past events. I don't think he's laying teenagers.
xd Even if it isn't a personal song, that doesn't mean he's bullshitting it either. It's probably just trying to make a statement. It's hard to say.
So I'd guess it's either not personal, or if it is, it's reflecting on past events. Hard to write angsty songs about romance when you're happily married, but it also doesn't mean you can't remember what it was like haha. If that is the case, it would explain why it sounds so cheerful and perky but the lyrics are so dark.