Love letters written by Bob Dylan during late 1950s sells for nearly $670K

BOSTON — Long before he was tangled up in blue, Bob Dylan was writing love letters.

>> Read more trending news

A collection of 42 letters written to a high school girlfriend by the iconic singer-songwriter was sold at auction to a Portuguese bookshop for nearly $670,000.

Boston-based RR Auction announced the sale on its website. The auction closed on Thursday, and the final cost, including the buyer’s premium, was $669,875.

The Livraria Lello in Porto, Portugal plans to keep the archive of 42 handwritten letters totaling 150 pages complete and available for Dylan fans and scholars to study, according to The Associated Press.

Dylan, 81, a native of Hibbing, Minnesota, wrote the letters to Barbara Ann Hewitt between 1957 and 1959, when he was still known as Robert Zimmerman, according to a news release from the auctioneer.

Hewitt was born in St. Louis County, Minnesota on April 28, 1941, according to Minnesota birth records compiled online by She was a month older than Dylan and was a sophomore at Hibbing High School in 1957, sitting in the same row in history class with the future singing star, RR Auction said in its auction listing.

They began dating after attending a holiday party on New Year’s Eve in 1957 and started exchanging letters when Hewitt and her family moved to the Minneapolis suburb of New Brighton.

The letters were written until at least 1959, RR Auction said. In 1959, Hewitt attended Mounds View High School in Arden Hills, Minnesota, according to

Hewitt’s daughter found the letters after her mother died in 2020, according to the AP. The original envelopes addressed in Dylan’s handwriting were sent to the Hewitt family’s home in New Brighton.

Also included in the lot was a signed Valentine’s Day card and a brief unsigned handwritten note. In his letters, Dylan expresses his affection for Hewitt, invites her to a Buddy Holly concert, writes poetry and discusses the music he was listening to.

Hewitt’s daughter told RR Auction that Dylan called her mother sometime in the late 1960s after he became famous and asked her to come to California, but she refused.

Hewitt was a redhead, and RR Auction Executive Vice President Bobby Livingston, a big Dylan fan, told the AP he believed that Dylan’s references to redheaded or auburn-haired women could have been inspired by Hewitt. That includes “Tangled Up in Blue” where in the opening stanza line Dylan wonders “if her hair was still red.”