He does it in not a sad way though. He could sing about cutting his veins in a hot bath and it'd still sound like he is on picnic.
Depressing Thread
Joseph King
Logan Murphy
...
Ryan Flores
if you stumbled upon just about any lyric from that album written on a scrap piece of paper by a friend, you'd at the least ask if they're okay. I think the delivery is just the way he is as a person where at his core he is positive. C&L is definitely his 'sad' album though