Petty met Nicks and asked him half-jokingly if he could write her a song that she could record for her first solo album. Petty didn't take her request seriously at first. Nicks reiterated her request a year later . Petty wrote a ballad called "Insider" at his home, and sent the demo to Nicks. After listening to the demo of "Insider," Nicks visited Petty at his studio,and gave the tape to Petty, saying, "You love this so much... YOU take the song." He did, and included it on Hard Promises.

Shortly after "Insider" was finished, Petty recorded a song that he and guitarist Mike Campbell composed about a year earlier - "Stop Draggin' My Heart Around" - and sent that demo to Nicks. She loved it, saying, "That's what I wanted all along." Eventually Nicks and Petty decided to do it as a duet and recorded their voices over the demo's instrumental track.