Is it gauging of worth, though, or is it simply a statement? It's clear to me he has some unhealthy, incorrect attitudes towards sex ("prime teen pussy", wtf), however I can also relate to base feelings of "desperation" due to lack of getting laid.

I'm not gauging my worth at all; I'm worth enough. I'm secure in who I am, confident enough, etc. But I can observe that there's been no rain in the valley for 7-ish years & I can factually say, "This lack of sex fucking sucks".