“I Wish You Would” is a song that I wrote with Jack Antonoff and it’s the first song that we work on together. I think, for this song, we wanted to create sort of a John Huges movie visual, with pining and, you know, one person is over here and misses the other person, but it’s too prideful and won’t say it, meanwhile, this other person is here and missing the same person, they’re missing each other, but they are not saying it. I had this happen in my life, and so I wanted to kind of narrate it in a very cinematic way, where it’s like, you’re seeing two scenes play out, and then in the bridge, you’re seeing the final scene, where it resolves itself. So, it says, “It’s a crooked love in a straight line down / Makes you wanna run and hide but it makes you turn right back around,” so it’s kind of that dramatic love that’s never really quite where it needs to be and that tension that that creates.

— Via Yahoo! Live

She talked about the song in the voice memo for it.

This is another way I’ve written songs recently. This is a song I did with Jack Antonoff, and Jack is one of my friends and so were hanging out and he pulled out his phone and goes ‘I made this amazing track the other day. It’s so cool, I love these guitar sounds.’ And he played it for me and immediately I could hear this finished song in my head, and I just said ‘Please, please let me have that. Let me play with is, send it to me.’ And so he sent it to me and I was on tour and this was me playing the track on my laptop recording me singing the vocal into my phone and it ended up being a song called “I Wish You Would”, because Jack wrote back and said ‘I love that’. So this is another way of writing, it’s writing to track:

“He drove past her street every night”.