Not sure exactly why, but whatever the reason, he's up front about his daddy issue.
Well good luck with all that I guess. LOL!
Milo is openly homosexual and uses some stereotypical mannerisms as armor. For example, he refers to his current speaking tour as the Dangerous Fa*got Tour. (Think of a Black Panther who “reclaims” the N-word.) So he refers to a dominant older male whom he finds appealing as “Daddy.” (No, I don’t think Milo finds Trump attractive, but he loves to mess with liberals’ heads.)