Pop singer Britney Spears' letters to high school boyfriend up for auction

Letters written by a teenage Britney Spears to her high school boyfriend are among the memorabilia up for auction this weekend.

The pop star was dating Donald “Reg” Jones in her hometown of McComb, Missouri, shortly before the career launch that would catapult her to global fame.

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Spears broke up with Jones in a two-page, handwritten note that said: “Look, I’m really sorry that it had to be this way, but I think we both knew this was coming.”

She later wrote: “I’ve had a great two years. Who knows, two years from now or even 10, we might get back together if it’s meant to be.”

Spears wrote him a second letter in August 1998, which is postmarked from the New York apartment she was living in while Jones was still in Missouri.

“What was wrong with you at lunch? You were mean,” she wrote. The note apparently included expletives but Spears signed off with a love heart.

The letters are expected to fetch between £2,800 to £4,250 when they go on sale at Julien’s Auction Music Icons event in Beverly Hills this weekend.

“What was wrong with you at lunch? You were mean,” she wrote. The note apparently included expletives but Spears signed off with a love heart.

The letters are expected to fetch between £2,800 to £4,250 when they go on sale at Julien’s Auction Music Icons event in Beverly Hills this weekend.

“It was a school friendship that developed into a relationship and then she was having a hard time trying to break the relationship, she didn’t see a future for them,” he said.

“It’s really very heartfelt, genuine from her to him and from him to her,” he added. “It’s also unusual to have both sides, if you will, represented in different letters in the one auction. They’re getting a lot of interest.”

Spears has returned to the public eye in the past few years due to the ongoing battle over her controversial conservatorship.

Two documentaries exploring the matter were released this year, including the New York Times documentary Framing Britney Spears.

In April, Spears said she was “flattered” that the world is “concerned with her life”.

Among the other items up for auction this weekend are Bob Dylan’s handwritten lyrics for his 1969 song “Lay Lady Lay”, which have a pre-auction estimate of £250,000 to £425,000.

Meanwhile a self-portrait caricature by Kurt Cobain, signed “Kurdt Kobain Rock Star”, could fetch £14,000.

The Independent