I was thinking because they were about the same age and both New York playboys.
Trump 1946
JFK Jr 1960
Definitely both NY playboys
And on a first name basis.
https://www.quora.com/What-did-JFK-Jr-say-about-Trump-in-the-George-magazine
Berman said Kennedy flew a select group of advertisers to Trump’s Mar-a-Lago estate. The 1996 gathering followed an industry conference in Florida.
Donald Trump attended the Mar-a-Lago gathering.
Talk soon turned to whether JFK Jr. could envision himself running for president. Trying to deflect the presidential speculation, Kennedy noted the Trump estate was far more glamorous than a Kennedy family compound a few miles away, the New York Post reported.
“I think you should be asking those questions of Donald,” Kennedy said, Berman recalled.
***********
Snopes says they looked in the June issue and the quote from the meme (my dear friend) was not there. Just the photo.
https://www.snopes.com/fact-check/jfk-jr-trump-unstoppable/
JFK Jr. and Donald Trump did have a social relationship, as demonstrated by this meme’s utilizing a genuine photograph of the two attending a New York Knicks basketball game in March 1999.