With the song written in 1971, and saying, "You had me several years ago, when I was still quite naive" persuades me that it's about someone she was involved with in the 60s not the 70s, and before she came to have any sort of real fame (which began in perhaps 70-71) and was younger. As the Mama Cass lover "mystery" {mentioned above) shows us, even if you're close to the family, finding those never-became-famous names can be an exercise in chasing nameless shadows, and CS has never indicated this was anyone particularly well-known at all (other than to her memory, of course).
While that might mean it could be a dead-end for us to try to figure out here, maybe not. Obviously she recalls who she had in mind. So why not check her remembered-and-written account of those years when she would have been "naive" and then working her way through Struggling Musician World, and see who has made enough of an impression for her to include a mention many years later.
Then if I was intent on figuring out the answer, I would
1 make a list of every possible relationship she mentioned in her account,
2 explore each of those possibilities to see if any stand out, and
3 see if any can be eliminated, or might be more likely, using the events and descriptions in the song.
Here is exactly what she wrote about those years, from when she was 19 to about 25:
Lucy and I taught ourselves guitar (three chords each) and hitchhiked up to Provincetown, MA in the summer of '64. We sang at a local bar called The Moors. Our repertoire consisted of folk music, peppered with a few of our own brand new compositions - the most famous and delightful of which was my sister's musical interpretation of Eugene Field's Wynken, Blinken and Nod.
We were signed to our first recording deal (Kapp Records) that year and Harold Leventhal and Charlie Close became our managers. We played the Bitter End and the Gaslight clubs in Greenwich Village, opening for Woody Allen, Bill Cosby, Dick Cavett and other soon-to-be-famous people. We wore matching dresses and caught the train, very late at night, back to our schools in the private sector.
Fancy schools. Quiet campuses, where dorm mothers frowned upon our late night arrivals and professors thought even less of overdue papers. I left school after a few years and went to live with my boyfriend in the south of France. While there, I had the first of many nervous breakdowns, brought on by an allergy to the local wine. My sister had had enough of my nerves and got married to a psychiatrist and had a child, Julie. About her I wrote Julie Through The Glass, which I later performed on my album Anticipation - but I won't go there quite yet.
Once Lucy was married, I got involved with manager Albert Grossman. Without my dear sister's protection, I was a sitting duck. He offered me his body in exchange for worldly success. Sadly, his body was not the kind you would easily sell yourself for. My record, produced by Bob Johnson was shelved - which was a shame because it was actually quite good.
When this didn't work, Albert got Bob Dylan to re-write an Eric VonSchmidt song for me, called Baby Let Me Follow You Down. It was good - funky. I was backed by Robbie Robertson, Paul Griffin, Mike Bloomfield and Levon Helm. But that ended up on the shelf too. Then followed another attempt at commerciality, in which Grossman teamed me up with Richie Havens - as Carly and The Deacon - but the team never made it into the studio. After this I fell into silence for another few years.
