he'd lost his virginity, rating the experience  about a 7 or so. Nothing really great. 

6 Big Black was known for his dynamic with Stern's on-air sidekick, Robin Quivers, who is seen above with Stern in 2014. Mike Coppola

6 He said he had  no friends  in the 2011 interview. Howard Stern Show

He shared that following the encounter, she'd refused a second date, giving him  kind of an excuse deal  at the time.

 Right now, I'd say I have no friends,  he said. He concluded the interview by declaring,  I hate the world, man. That's how it is. 

Meanwhile, Stern - who has been battling toxic workplace claims by ex-assistant Leslie Kuhn - recently confirmed a lucrative deal with HBO Max to stream his show by condensing it into a series.