10 Women Bob Dylan Has Dated
Bob Dylan has been relatively tight-lipped about the people he has dated. He has had multiple romantic relationships, though.
Barbara Ann Hewitt
Long before he was famous, Dylan was a high school student in Minnesota who had fallen in love with his classmate. He wrote many love letters to his then-girlfriend, Barbara Ann Hewitt.
The letters, in which Dylan invites Hewitt to events and writes about the songs he likes, sold for nearly $670,000 at an auction in 2022.
Mavis Staples
Dylan and Mavis Staples played overlapping shows, and Dylan quickly developed a case of what Staples described as “puppy love.” He spoke to her father about proposing, but never did.
“I still have letters that we would write to each other,” she told The New Yorker in 2022. “[T]he only time we would see each other was when we happened to be on the same show … I was the one that dodged a bullet. I wouldn’t have been able to keep up with him.”
Suze Rotolo
One of Dylan’s more notable relationships was with Suze Rotolo. In Chronicles, Dylan wrote that he was stunned by the sight of her when they first met. Rotolo guided Dylan on his political awakening and inspired his early love songs.
The couple broke up, a casualty of Dylan’s rising fame, but she holds a permanent place in his catalog. Rotolo and Dylan walk arm in arm on the cover of his 1963 album The Freewheelin’ Bob Dylan.
Joan Baez
Dylan was involved with collaborator Joan Baez while dating Rotlo. She used her platform to bring him exposure. Their romance came to an end when Dylan got married, but they collaborated over the years. By 2010, though, they had fallen out of contact, and Baez avoided him at the White House’s Civil Rights Concert.
“The chances of him just walking past me would be too awful a scenario,” she said, per Rolling Stone. “It would just bring up feelings that aren’t necessary.”
Dana Gillespie
Dana Gillespie is a musician and actor who became involved with multiple musicians. At a 1965 press conference, Dylan picked Gillespie out of the crowd and invited her back to his hotel room. She later joined him on tour.
Gillespie told The Guardian that Dylan was “smart and funny – really interesting to be around. I don’t often find Americans attractive, but he certainly was.”
Sara Dylan
Dylan’s first marriage was to Sara Dylan. They wed in 1965 and shared five children. The nuptials came as a surprise to those who knew Dylan, though.
“Bob’s desire to get married to Sara surprised me,” Dylan’s road manager Victor Maymudes wrote in his book Another Side of Bob Dylan: A Personal History on the Road and Off the Tracks. “I asked him about it. ‘Why Sara?! Why not Joan Baez?’ He responded with, ‘Because Sara will be home when I want her to be home, she’ll be there when I want her to be there, she’ll do it when I want her to do it. Joan won’t be there when I want her. She won’t do it when I want to do it.'”
The couple divorced in 1977.
Ruth Tyrangiel
One of Dylan’s longer relationships was with actor Ruth Tyrangiel, who says their relationship began in 1974. She played the “girlfriend” in the 1978 film Renaldo and Clara and allegedly had a 19-year affair with Dylan.
After their relationship ended, Tyrangiel filed a palimony suit against him. She claimed she became his “nurse, confidante, companion, homemaker, housekeeper, cook, social companion [and] advisor” (via Down the Highway by Howard Sounes.) A judge dismissed the case.
Carolyn Dennis
Dylan’s second wife, Carolyn Dennis, was one of his backup singers. They kept their relationship a secret for years. More secret was the daughter Dylan and Dennis shared. Some accused Dylan of being an absent father, which Dennis denied.
“To portray Bob as ‘hiding his daughter’ is just malicious and ridiculous,” Dennis said in 2001, per ABC News. “That is something he would never do. Bob has been a wonderful, active father to Desiree.”
Britta Lee Shain
Dylan also began an affair with his road manager’s girlfriend, Britta Lee Shain. According to Shain, Dylan pursued her throughout her relationship with his manager. Eventually, they began a romantic affair that stretched several weeks.
Ultimately, their relationship ended when Shain confessed to her boyfriend, who broke the news to Dylan’s girlfriend.
Chris O’Dell
Chris O’Dell was a former employee at The Beatles’ Apple Corps who has recounted affairs with musicians. She worked with Dylan as a tour manager and also had an affair with him.
“He’s a very intense, private person,” she told The Daily Mail. “He doesn’t share a lot of himself — in many ways he’s very guarded — at least that’s the way I found him at that time … I loved working with him.”
