Serving as his longtime friend and special confidante, Lem Billings was JFK's best friend of nearly three decades up until his Kennedy's assassination. Upon meeting at Choate high school, Kennedy and Billings were inseparable. However, unknown to many, Billings even had his own room at the White House, where he was able to soothe JFK's temperament in dealing with political affairs. But this isn't to say that Kennedy and Billing's relationship ever consummated into a romantic one, it was purely a deep platonic relationship. The extent to their friendship could easily be captured by the fact that JFK was buried with a friendship namesake: a whale scrimshaw which was a gift from Lem. While it was never absolutely confirmed, everyone knew that Lemmings was gay but was kept silent as not to tarnish the Kennedy legacy at the time. However, it was speculated that Lemmings had deeper feelings for the President: "Jack made a big difference in my life. Because of him, I was never lonely," stated Lemmings in personal documents. "He may have been the reason I never got married."

[via Woolf and Wilde]