Ginger Jordan

Britney Spears’ letters to her high school boyfriend going on auction block next month

Getty Britneyspears1998 052421

Britney Spears can’t catch a break. Not only was her personal life splashed all over the headlines at the height of her fame, but now details of her personal life in her pre-fame days are being put on the auction block by her old high school boyfriend.

Juliens Auctions is selling handwritten letters penned by Britney to her boyfriend Donald “Reg” Jones when she was living in New York City and he was living in Mississippi.  There are two lots: one letter, and a letter and an envelope, each of which has an estimate of $4,000 to $6,000.

In one of the letters, penned in 1998, Britney takes Reg to task for treating her badly, asking, “I don’t trust you, especially after what you said last night. My mom was almost right, you are like a caring friends [sic], but f**ks me whenever you like.”  She also called him “you a**h**e,” but signs it with a heart.

The second letter is a breakup note, with Britney telling Reg, “Look, I’m really sorry that it had to be this way, but I think we both knew this was coming….I know it’s really hard to have a girlfriend who travels, but it is even harder to have a boyfriend who doesn’t have trust in his girlfriend!”

“You literally pushed me away. I couldn’t take it anymore!” she continued. “I’m not in love w/ you anymore, but will always care about you…who knows, we may even get back together…but right now you need to let me go.”

The Music Icons 2021 auction takes place Friday, June 11, Saturday, June 12 and Sunday, June 13, live in Beverly Hills and online at