i've told him repeatedly that his desperation leads to a vicious cycle where his desperation scares women off making him even more desperate. i told him working out regularly would help. at the very least mask it until he can find someone to quench his thirst, so to speak...
but that's not even it, he won't talk to women sometimes. and if he does he won't make his intentions known, like he befriends women hoping it'll lead to sex.
for example, there was this girl in one of his classes last year he had a big crush on. she wasn't in his program but they had a class together anyway. she normally sat between him and the lecturer so he said he had a hard time focusing in that class. so i told him to strike up a conversation, ask for her number perhaps. he told me that after class they had the same route for a good 5 minutes before their paths diverged. so for an entire term he had many easy chances to talk to her but instead every time he just walked behind her staring at her ass.
Another story:
S made friends with another PhD student, I'll call her A, who's five years his senior. They have a lot of classes together, and they are pretty good friends from what he tells me, although I've never met her. They text a lot.
Anyway, one night A got really drunk when they both went to a bar so S hung out with her so she could sober up and get herself home. A nice thing that friends do for friends, right? Anyway, months after that night he brought it up again saying "She owes me."
I'm like, "What? What does she owe you for?"
"Well, I took care of A when she was blackout drunk. I could have done anything to her and she wouldn't have known, but I didn't."
I was just flabbergasted and asked him if he considered A to be his friend or not...
The idea stuck with him though because later on he messaged me about how being around her makes him hard and he's gonna grab her one of these days. I thought he was joking and messaged him back "don't be a rapist." But a couple messages later he talked about how he was going to bars often with her and that "maybe after one of these pubs i can take advantage of her a little bit since she can't even tell what's going on." I wasn't concerned though, and nothing's happened between the two.