Carly Simon stopped by with her band and admitted she suffered from such an extreme case of stage fright that she needed a pre-show smack on her ass before performing live. Howard asked Carly's son, Ben – who's also in her band – if he liked preferred performing with his mom or his dad (James Taylor), Ben said it was difficult to compare, because his dad's a road-seasoned veteran and getting his mom on stage was "like pulling teeth."
Howard asked Carly why she had such a hard time getting along with James, but Carly replied that they don't really have a relationship at all: "I don't know his email or phone number...I would be so happy to talk to him, even [with] the bad feelings I have." Howard wondered when Carly last reached out to James, and Carly responded quickly: "A year ago." Howard told Ben that he needed to facilitate a reconciliation, but Ben thought it was a long road: "It's difficult for me to hear bad things about my mom...whenever I see [James] he says to send his kindest regards."