The linked TikTok is amusing, but not really accurate. Lem Billings was one of JFK's adolescent friends and this friendship lasted through JFK's life. And Billings was gay and very likely harbored romantic feelings for Kennedy. However, the evidence suggests that this was a one-sided relationship.

For example, in 1934 Lem wrote to Kennedy a letter written on toilet paper while the latter was convalescing in one of his many hospital visits. What the letter said was unknown, but letter-writing on toilet paper was a common tradition in British and American boarding schools for boys wanting to arrange for a liaison, the idea being that the evidence could be quickly destroyed. We do not know the contents of the letter, but Billings did preserve Kennedy's response:

Please don't write to me on toilet paper anymore. I am not that kind of boy

Now this is not to say there was no homoerotic aspects to their relationship. There was a lot of "guy stuff" the two men did that went a bit beyond normal friendship. For instance, Kennedy had taken Billings earlier in 1934 to a prostitute so both men could lose their virginity to the same woman. While Kennedy went first, Billings waited outside of the door and later could not go through with it. Kennedy's letters to Billings often went into graphic details about his body, especially his genitals. Billings was also a willing third wheel on some of Kennedy's dates who would stand by while Kennedy necked with his current girlfriend.

Kennedy was most likely aware of Billing's attraction to him. Yet what is notable about their relationship is that Kennedy did not ostracize his friend. While this might seem noble, it was part of an emerging pattern in the young man's life where he would cultivate intense friendships in which would become quite one-sided. JFK expected loyalty and devotion from these people, but he could be very reluctant to reciprocate this affection. A number of JFK's friends turned staffers found themselves working to the bone for Kennedy. Billings was one of many of JFK's friends who quickly became a courtier of sorts in his entourage.

None of this is to preclude the possibility that JFK had a same-sex encounter. This was common in gender-segregated world of boarding schools like Choate. But it is dangerous to project contemporary sensibilities as seen in the linked TikTok onto the past. The all-male culture of Choate might look to contemporary eyes as quite gay, but that does not mean people in the past saw themselves in that way. All the available evidence supports that Billings was not a lover, or as the TikTokker says, "a live-in twink."

Sources

Logevall, Fredrik. JFK. Coming of Age in the American Century, 1917-1956 Volume 1. New York: Random House, 2020.

Pitts, David. Jack and Lem: John F. Kennedy and Lem Billings : the Untold Story of an Extraordinary Friendship. New York: Da Capo Press, 2008.