He just fucks up with everything he tries. The joke is supposed to be "my future ex-wife." That's confident but self-deprecating and it's such an over-the-top expectation nobody will actually take it seriously. So it earns a hearty chuckle and -- more importantly -- doesn't scare the ever-loving shit out of whatever poor woman is on the receiving end. This is just stalker material.
I can't stand him at all. He's just so god damned irritating and full of himself. I'd hoped that the weeb wars case going so tragically sideways might have sobered him up a bit (lol) but nope, he's even louder and more obnoxious than ever. Seriously, fuck Schupp though. Dumb old fart.