He had a relationship with Joan Baez.

Dylan met his future bride, Joan Baez, a famous folk singer. Joan Baez had just produced her debut album and was heralded as the "Queen of Folk Music" when she first met Dylan in April 1961. Baez later remarked, "I never dreamed that anything that powerful could come out of that little toad," after hearing Dylan sing "With God on Our Side."

Baez encouraged Dylan to perform with her on stage at the Newport Folk Festival in July 1963, paving the way for related duets over the ensuing two years. It is well known that Baez gave Dylan his big break by inviting him to perform in front of her devoted following. Many Baez supporters objected to this incursion and disliked Dylan's nasal vocals. The relationship between the two changed as their music did thanks to Baez's ongoing faith in Dylan.

By the mid-1960s, Dylan was playing hundreds of concerts annually, and his relationship with his girlfriend started to take a back seat to his work. He vowed to bring her on stage with him, as she did for him when she was the bigger star but then failed. Not so that they did not accompany each other, in the 1965s, they joined his European tour together.

Baez goes back to the US. Years later, Dylan acknowledges that he regrets how his relationship with Baez ended, regardless of whether he hinted at his infidelity or broke a vow to come back. It's still unclear how she reacted to his kindness when he was a struggling amateur artist.