Given his filthy greasy glasses, eye dessication, and probable face blindness from autism, I honestly wouldn't be surprised if he literally can't tell a pretty girl from an ugly one. That's why he incessantly stalks celebrities and e-thots; the hundreds of other greasy unwashed losers drooling over these women confirm to him that yes, they are high-status for being pretty. But Russ knows that any woman is a step up, status-wise, from no woman, and her being the same room as him means that she's that much closer to sucking him his penis. That's why I think that even if he got a girlfriend he wouldn't be satisfied with her and would keep "wooing" celebrities and e-thots. If he got an e-thot girlfriend, he would keep wooing celebrities. And if he got a celebrity, she wouldn't miraculously fix all his life problems, and he would go looking for another one.