I would say 2015, after Obergefell v. Hodges made homersexual marriage the law of the land, and they lit up the White House in the gay rainbow. Honk honk.

You have to remember that Obama ran for president in 2008 on a platform that marriage was between a man and woman, something that almost seems like reverse-clown-world these days. The iPhone first debuted in 2007, and clown world intimately depended upon it and upon Twitter, which launched in 2006. Both took time to change the previous online culture from one which valued intellectual meritocracy, free speech, debate, and words to today's "mean girl" cancel culture which values emotions, conformity, tantrums, and pictures.

Gay marriage was for most of the 20th century considered the ne plus ultra of liberalism, the impossible dream of the left, and when it came true, you could literally feel the crazy seeping into the breach it had created. "What now?!" seemed to be the words on every liberal's lips. The trans movement inserted themselves as the next impossible dream: destroy gender itself. And it's pretty much been clown world ever since.