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Sweetheart Like You: Bob Dylan’s love letters to his old girlfriend up for auction


Got a cool quarter mil? You may want to invest in a treasure trove of old love letters that young Bob Dylan wrote to his high school sweetheart.

The 42 letters are currently up for sale by the Boston-based RR Auction house, and the starting bid is $250,000. In the letters, addressed to Barbara Ann Hewitt of New Brighton, Minnesota, Dylan — then named Bob Zimmerman — writes about preparing for the Hibbing High School talent show, as well as his dreams of selling 1 million records and changing his name. 

In other letters, he asks Hewitt to go with him to see Buddy Holly in Duluth and discuses the records he’s been listening to, as well as the cars and fashions of the late 1950s. He also, according to the auction house, “professes his never-ending affection,” signing the letters “Love, Bob.” All the letters come with the original envelopes — and there’s even a Valentine’s Day card in there.

The trustees of Hewitt’s estate want to keep the archive together, which is why the letters are being sold as one lot. Individual letters by Dylan have sold for as much as $30,000.

If your pockets aren’t that deep, other items from the Hewitt estate that are up for bid include signed photos, an original sketch, a collection of handwritten poems, and signed and annotated lyric sheets.

If you’re not a Dylan fan, the auction, which ends November 17, also includes items from The Beatles, Pink Floyd, Queen, Led Zeppelin and The Doors.

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