Lyric discussion by cubbyblues 

Cover art for All We Are lyrics by Matt Nathanson

He didn't appreciate the relationship when he had it. It's kind of the theme of the newer album.

He knows now in retrospect what he didn't realize in the moment. He tasted love so sweet, but it was lost on him.

The part about going broke believing simple was hard basically states he lost love by overanalyzing everything when he was in the relationship and making it difficult. He should have just gone with it and enjoyed it.

"It's hard to change the way you lose if you think you never won" goes back to how in the moment, he didn't realize what he had. Maybe it was his first love. But now he definitely knows what he lost and what he had "won" when he had her.