She continued to work on music throughout the 1960s, but at a slower pace, while taking various jobs including a stint as the editor of the influential Journal for Conflict Resolution in Michigan. In letters to loved ones, written just before she vanished, she said she had struggled in life "to find a place to plug in".

What happened to her when she went missing remains unknown – in 2023's To Anyone Who Ever Asks: The Life, Music and Mystery of Connie Converse, the definitive biography about her, the author Howard Fishman writes how some believed she drove her car off a cliff in Canada, while others had claimed she started a new life in Brazil.

Whatever the reality, Converse's never-solved disappearance certainly provided her music with an extra point of intrigue when, decades later, it came to public attention. In 2004, the late producer Gene Deitch debuted on WYNC radio some of her songs that he had recorded at private dinner parties in 1954 and 55, creating a surge of interest in this musical enigma, and resulting in the 2009 release of How Sad, How Lovely. The album also featured bedroom recordings Connie made, which are punctuated by endearing nervous coughs. Now its vinyl re-release comes at a time when Connie's stock is particularly high, especially after a recent glowing Pitchfork review and her songs being covered by everyone from Karen-O to Bill Callahan over recent years. 

"I first thought this Connie Converse character had to be a hoax or a gimmick," laughs author Fishman, who is also a band leader. "These songs were too fresh, too modern, too anachronistic to have been recorded in the 1950s."

Converse was raised in Concord, New Hampshire in a right-wing Christian household, in which alcohol and the discussion of sex were outlawed [her dad was proudly part of the pro-Prohibition Anti-Saloon League of New Hampshire]. Her music provided a raw autobiography of her time escaping this strict upbringing and living freely in New York City. She was also bravely attempting to make female promiscuity and sexual empowerment less taboo.