Dax Shepard once overheard Billy Crudup engaged in a very intimate moment. "I one time had the rare honor of hearing Billy make love," Shepard, 50, said during the Monday, November 17, episode of his "Armchair Expert" podcast. "I want to keep it as clean and not offensive to Billy as possible, but I've never ever, ever heard someone receive that much pleasure in my life. I felt very inept and insecure." Crudup, 57, said he has thought about the moment "many, many times" and is "convinced there were other people in the house" who were making all the noise, not him and his partner. "I just was like, 'When's this gonna end?'" Shepard joked. "But anyways, when I saw Billy, I just had to tell him, I think about that often, and that was 20 years ago." Mary Louise Parker and Billy Crudup: The Way They Were Crudup quipped that Shepard has "been in the gym" ever since because he's "trying to compete" with the Almost Famous star. "Kristen's never made noises like I heard some 20 years ago," Shepard added, referring to wife Kristen Bell. While Crudup didn't share any hints about his partner in the bedroom at the time, his wife, Naomi Watts, opened up earlier this year about their first time having sex. "I'm not going to embarrass him and talk about it in depth on live TV, but I was mortified because I had my patch on," Watts, 57, said on The Drew Barrymore Show in January, referring to a transdermal skin patch she wore to help alleviate menopause symptoms. "If anyone's ever worn a patch, you know that they're very sticky, the adhesive takes ages to get off," she continued. "In fact, my first doctor that told me to wear the patch said just use car oil, that'll be fine. And I'm like, 'I don't want to use car oil on my body.'" Amy Sussman/Getty Images Watts, who also detailed the awkward encounter in her memoir Dare I Say It: Everything I Wish I'd Known About Menopause, ultimately tried to take the patch off by peeling it away. When things escalated between her and Crudup, she said she "excused myself, ran off to the bathroom and panicked" about the gunky outline the patch left on her skin. "I probably [had] a couple of them on both sides," Watts added. "And I was in there too long, and then came out sort of like that, frantic, and he said, 'Are you okay, are you not in the mood?" Watts ultimately decided to come clean to Crudup and recalled telling him, "No, I just, well, look, I'm in menopause and I have treatment and I have this patch and I'm wearing it and it leaves this... I'm old, should I just leave?" Crudup responded, "We're the same age. We're the same age. What is this? This is science. How can I help?" Crudup met Watts while filming Gypsy in 2017, one year after her split from Liev Schreiber, with whom she shares sons Sasha, 18, and Kai, 16. The couple tied the knot in New York City in June 2023, followed by a second ceremony surrounded by their family in Mexico one year later. Billy Crudup's Dating History: From Mary-Louise Parker to Naomi Watts The Morning Show actor was in two other high-profile relationships before his marriage to Watts. He began dating Mary-Louise Parker in 1996 after they met as costars in the Broadway play Bus Stop. In 2003, when Parker, now 61, was seven months pregnant with their son, William, Crudup left the actress to pursue a relationship with Claire Danes, his costar in the 2005 film Stage Beauty. While Parker has not directly addressed what happened between her and Crudup, she alluded to their split in her 2015 memoir, Dear Mr. You. "I am alone. Look, see? I am pregnant and alone. It hurts to even breathe," she wrote in a letter to the New York City cab driver who got lost while driving Parker to a doctor's appointment. Crudup and Danes, 46, called it quits in 2007. The Homeland actress briefly opened up about their breakup in a 2009 interview with Blackbook. "That was a choice I made to fall in love," she said. "It's unpleasant to be cast in such an unflattering role [in the tabloids], but I just had to remain steadfast. I was living with the same kind of integrity that I had always lived with."