Somebody who makes a harmless fool of themselves often and is endearing for it, while also being extremely whorish in their demeanor (this is especially the case if they are not often successful in their romantic endeavors).
Someone who has embraced their cringeworthypersonality and interests without regard to what other people think about them, pursuing happiness instead.
P1: Did you hear Jake joined the anime club? What a loser!
P2: Nah he's cringepilled. I respect that he's pursuing his interest, and it seems to make him happy, so good for him.
P1: Actually... that's the most based thing you can do. Respect.
White bitch: Oh my gooood I just finished reading that One Direction smut. It was so fucking hot.
Boyfriend: You need to stop reading that cringefiction.