Bob Dylan is the very definition of a living legend, and for over 60 years, he’s been known not just for his poetic lyrics and distinctive vocals, but also for his eternally enigmatic presence.

Bob Dylan’s first girlfriend: Echo Helstrom

Bob Dylan (then known by his birth name, Robert Zimmerman) met his first girlfriend, Echo Helstrom, in the late ’50s at high school in Hibbing, Minnesota. They attended the junior prom together and were a couple for about a year before they broke up in 1958.

The young couple shared a love of music. They would spend hours listening to rhythm-and-blues on the radio and playing her family’s old country records. Dylan was inspired by Helstrom’s free-spirited nature and musical knowledge, and at one of his first-ever performances at his high school auditorium he played a song with the line, “I got a girl and her name is Echo.”

Many fans and critics have speculated that Helstrom inspired his 1963 song “Girl From the North Country.” Dylan inscribed, “Let me tell you that your beauty is second to none. Love to the most beautiful girl in school,” in Helstrom’s yearbook, and in his 2004 memoir, Chronicles: Volume One, he wrote, “Everybody said she looked like Brigitte Bardot, and she did.”

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Helstrom went on to work behind the scenes in the film industry and passed away at 75 in 2018.

In college, Dylan briefly dated future actress Bonnie Beecher, and some of his earliest recordings were made at her home in Minneapolis.

Bob Dylan’s ’60s muse: Suze Rotolo

Artist and activist Suze Rotolo was a major influence on Dylan during his early days in the ’60s. The couple met at a New York folk concert in 1961, and it was love at first sight, with Dylan recalling in his memoir, “She was the most erotic thing I’d ever seen. She was fair-skinned and golden-haired, full-blood Italian. The air was suddenly filled with banana leaves. We started talking and my head started to spin. Cupid’s arrow had whistled past my ears before, but this time it hit me in the heart and the weight of it dragged me overboard.”

Rotolo cultivated Dylan’s political consciousness thanks to her involvement in civil rights and anti-war causes, and this newfound awareness led him to write classic protest songs like “The Death of Emmett Till,” “Masters of War” and “Blowin’ in the Wind.” She also introduced him to the work of writers like Arthur Rimbaud and Bertolt Brecht, both of whom inspired his songwriting.

Most famously, Rotolo appeared arm-in-arm with Dylan on the cover of his 1963 breakthrough album The Freewheelin’ Bob Dylan. While the image of them became an icon of the era, their relationship didn’t last. Tensions rose due to Rotolo having an abortion and Dylan embarking on an affair with fellow folk singer Joan Baez, and they broke up in 1964.

Dylan wrote the 1964 song “Ballad in Plain D” about the end of their romance, and she was said to have inspired his early love songs “Don’t Think Twice, It’s All Right” (1963), “Tomorrow Is a Long Time” (1963), “Boots of Spanish Leather” (1964) and “One Too Many Mornings” (1964).

After the breakup, Rotolo continued her work as an artist and wrote a memoir about her time with Dylan, A Free­wheelin’ Time: A Memoir of Greenwich Village in the Sixties, in 2008. She died of lung cancer in 2011 at age 67.

Bob Dylan’s folk flame: Joan Baez

Dylan met Joan Baez through the New York folk scene in 1961, when he was dating Rotolo. At the time, Baez had recently released her debut album, while Dylan was still unknown. In 1963, she invited Dylan, who was by then a rising star, to perform with her at the Newport Folk Festival, and this led to many more duets, including one at Martin Luther King Jr.’s March on Washington that same year.

Dylan and Baez began their romance around the time they started performing together, and their affair led to the dissolution of his relationship with Rotolo. By 1965, Dylan’s fame had grown exponentially and when he invited Baez to join his tour but failed to actually bring her onstage, it was the beginning of the end. Dylan was also in the midst of an affair with model Sara Lownds, who he’d go on to secretly marry after she became pregnant later that year.

While Dylan and Baez’s relationship was brief, it had a sizable impact on both musicians’ lives, and they performed together several times after their breakup, as she toured with him during his Rolling Thunder Revue shows from 1975 to 1976, and she appeared in Renaldo and Clara, a 1978 film directed by and starring Dylan.

Dylan and Baez also shared the stage in 1982, and in 1984, they toured together for the final time. Baez ended up leaving the tour early, as she felt frustrated by the fact that her former flame was getting all the attention.

Baez wrote a number of songs about Dylan, including “Diamonds & Rust” (1975), which was inspired by receiving an unexpected phone call from him a decade after their breakup, and is considered one of her greatest achievements, while some have said that she inspired Dylan songs like “To Ramona” (1964), “She Belongs to Me” (1965) and “Visions of Johanna” (1966).

Even with all the drama in their relationship, Dylan has spoken highly of Baez, and in 2015, he said, “​​Joan Baez is as tough-minded as they come. Love. And she’s a free, independent spirit. Nobody can tell her what to do if she doesn’t want to do it. I learned a lot of things from her. A woman with devastating honesty. And for her kind of love and devotion, I could never pay that back.”

Bob Dylan’s first wife: Sara Lownds

Dylan met Sara Lownds, a former model, while she was working as a film production secretary in 1964. At the time, Dylan was still with Baez, but they soon began an affair, and when Lownds became pregnant with their first child, Jesse, now a director, in 1965, the couple secretly married, and Sara took his name.

Dylan and Lownds had a daughter, Anna, in 1967, and another son, Sam, in 1968. In 1969, their youngest child, Jakob, was born, and he went on to follow in his dad’s musical footsteps as the frontman of the Wallflowers. Dylan also adopted Maria, Lownds’ daughter from her previous marriage.

Dylan and his wife collaborated creatively when the two of them starred as the title characters in his experimental 1978 film Renaldo and Clara (which, in a bold move, also featured none other than Baez!). They divorced after 12 years of marriage in 1977, and Dylan’s classic 1975 album Blood on the Tracks is widely believed to be about the dissolution of their relationship.

Sara also inspired dreamy Dylan songs like “Sad-Eyed Lady of the Lowlands” (1966) and, of course, “Sara” (1976). Since their divorce, she has stayed out of the public eye.

In 1974, Dylan had an affair with Ellen Bernstein, who worked at his record label. She claimed that he wrote the 1975 song “You’re Gonna Make Me Lonesome When You Go” about their time together. He also had on-and-off relationships with actress Sally Kirkland and Ruth Tyrangiel, who later sued him for breach of contract, fraud, deceit and intentional infliction of emotional distress, and had a fling with his assistant, Chris O’Dell.

Bob Dylan’s secret second wife: Carolyn Dennis

In 1986, Dylan’s backing singer, Carolyn Dennis, gave birth to their daughter, Desiree, now an actress. Dylan and Dennis married later that year, and divorced in 1992. Their marriage and Desiree’s existence were kept secret until 2001, when the biography Down the Highway: The Life of Bob Dylan was released.

At the time the book was published, Dennis wanted to get ahead of the rumors contained within, and issued a statement saying, “Bob and I made a choice to keep our marriage a private matter for a simple reason — to give our daughter a normal childhood . . . To portray Bob as ‘hiding his daughter’ is just malicious and ridiculous. That is something he would never do. Bob has been a wonderful, active father to Desiree.”

In 1987, Dylan had a brief affair with musician Britta Lee Shain, who published a tell-all about their fling, Seeing the Real You at Last: Life and Love on the Road with Bob Dylan, in 2016.

Bob Dylan’s love life today

Today, in typically mysterious Dylan fashion, no one knows for sure whether the musician is married. Over the years, there have been many rumors about his love life, and some have even speculated that he’s secretly married to his assistant, Suzie Pullen.

Over half a century into his iconic career, it’s clear that when it comes to his personal life and the inspirations for his songs, Bob Dylan remains captivatingly unknowable—which only enhances his brilliance.