Rachel Fine, Jon Hein's 'Bonus Show' co-host, stopped by to discuss her recent break-up with HowardTV senior content producer Richie Wilson.
Richie came in to pre-empt her comments with a confession, saying the problem wasn't Rachel--it's him: "I do cognitive behavior therapy...I'm learning how to like myself...It's hard to let somebody love you if you don't love yourself...I [also] have some major trust issues."
Rachel said she'd started to notice a shift in Richie's behavior: "I do see changes in him. I want to see if they stick."
Richie said things were going well until Rachel found "an email I was sending another chick to go hang out with her." Howard thought Richie wasn't ready for a woman like Rachel ("Set her free. It's never going to work.") and told Rachel to exact her revenge with a staffer: "Want to mess his head up? Date Benjy."