Talking about the song on New Music Daily with Zane Lowe on Apple Music, Tedder said, "So 'Didn't I' came from a place of somebody very dear to me… A couple that got divorced and I'm surrounded… My parents, got divorced, my wife's parents got divorced. Everybody, you know? We have friends that are going through it right now and I had this idea that when you marry somebody or you choose to be with them, it’s because you've had a lot of beautiful moments and somewhere the discord gets in. But then once you have the distance, and it does break up, and you do go through that divorce, you still have those moments. You look back and you go, you know what? This ended in a disaster, but weren't we amazing, when we were amazing? Wasn’t it good? It wasn’t all bad. There was a moment, didn't I love you? Didn't we fly? Wasn't this everything we thought it was, until it wasn't? And so that's really what the song's about."[1][2]
Music video
A music video to accompany the release of "Didn't I" was first released onto YouTube on March 13, 2020.[3][4]