It’s no secret that John F. Kennedy was lucky with the ladies—and prolific in his extramarital conquests. Now, as Mark Pratt reports for the Associated Press, fans of presidential pecadillos can buy a love letter from the president to a secret mistress with a sad story.

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The letter, which is expected to fetch $30,000 or more, is being auctioned by RR Auctions in Boston. It’s a steamy note that shows JFK’s personal charm—and his love of particularly seductive dashes:

Why don’t you leave suburbia for once—come and see me—either here—or at the Cape next week or in Boston the 19th. I know it is unwise, irrational, and that you may hate it—on the other hand you may not—and I will love it. You say that it is good for me not to get what I want. After all of these years—you should give me a more loving answer than that. Why don’t you just say yes.

The letter is thought to have been written around October 1963 to Mary Pinchot Meyer. As Lance Morrow reported for Smithsonian Magazine in 2008, Meyer conducted a clandestine affair with Kennedy in the 1960s after her divorce from CIA agent Cord Meyer.

Meyer was a fascinating woman in her own right—the daughter of a Progressive Party philanthropist and a journalist, she herself pursued a career in the press at a time when women were still largely marginalized in the field. She briefly served as editor for Atlantic Monthly and brushed shoulders with Communists, pacifists and intellectuals over the years. She was also a talented artist. Those bohemian leanings are said to have perhaps softened JFK’s view of the Cold War during their years-long affair.

“It’s incredible to see the president writing something so personal,” Robert Livingston, RR Auctions’ executive vice president, told Pratt. The letter, written about a month before the president was assassinated, indicates that their affair was still alive—if on the rocks—shortly before he died.

Meyer’s own life was cut tragically short in 1964, when she was shot and murdered along a footpath in Georgetown. As Smithsonian’s Lance Morrow reports, her death still remains a mystery—the man who allegedly killed her was found not guilty. But it has fueled a thousand conspiracy theories about the CIA, the FBI, and the circumstances of Kennedy’s own death.

What really happened to Meyer? The truth may never come out. But one buyer will have the closest thing to the truth—a casually punctuated, heartfelt note that reflects some of the president’s innermost thoughts (and his flair for persuasive punctuation) during an all-too-fleeting moment in time.