I Try So Hard to Be His Friend
Published August 31, 2026
"I Try So Hard to Be His Friend" is a catchphrase pulled from a November 2017 tweet by U.S. President Donald Trump aimed at North Korean leader Kim Jong Un. Trump's passive-aggressive line, tucked into a tweet where he denied ever calling Kim "short and fat," inspired Twitter users to swap in their own targets, birthing a mock-apology template that ran through the late 2017 news cycle.
Overview
The joke lives in the shape of Trump's original tweet, a fake denial of an insult he had just delivered, followed by the wistful sign-off "Oh well, I try so hard to be his friend, and maybe someday that will happen"1. The line reads like a schoolyard non-apology dressed up in diplomatic language, which is exactly why copycat versions worked. Parodists kept Trump's phrasing intact and just replaced Kim's name with whoever they wanted to jab.
Common riffs pointed the mock apology at college professors, characters from He-Man and Doctor Who, celebrity feuds, and personal rivalries3. The comedic payoff comes from readers instantly recognizing the source and filling in the missing context, so the parody works without needing a caption or setup beyond the name swap.
Origin & Background
How It Spread
How to Use This Meme
The format typically keeps Trump's opening intact. Users swap in a target's name in the "Why would [name] insult me by calling me 'X,' when I would NEVER call them 'Y?'" line, then close with "Oh well, I try so hard to be [their] friend, and maybe someday that will happen." Common conventions include picking a target who has already insulted the user, or inventing an insult the target supposedly delivered so the fake outrage lands.