He has, in his own words, only had sex with two women. Iirc he said so in an older MATI episode? One of them was @FramerGirl420, an aspie and KF regular back from the CWCki Forums days. The other, I assume was some drunk bar skank Dax Herrera or whoever set him up with - he's mentioned his "friends" trying to set him up with chicks on MATI.
He hasn't been anywhere near a real woman in well over half a decade and his mental state has worsened since. He was always mentally ill but he's gotten significantly more obnoxious and abrasive over time.