Howard Stern put Conan in a tough spot with weird Lisa Kudrow questions but he handled it with class
Howard Stern has been a household name for 'The Howard Stern Show,' but since its launch in the 90s, Stern has often been called out for asking his guests some really offensive questions. In a March 2004 episode of the show, the late-night TV star Conan O'Brien appeared as his guest and answered some really hard questions about his relationship with Lisa Kudrow. During the show, Stern asked O'Brien, "Here's what I want to ask you. Let's get right to it. I had on Lisa Kudrow, who was your girlfriend for years." O'Brien, quickly correcting him, said, "No, no, no, technically not girlfriend for years; we were friends for a long time." Undeterred, Stern asked, "And then you were girlfriend and boyfriend," to which O'Brien conceded, "Yes, for a brief time." The conversation took a more intrusive turn when Stern started to push the boundary and asked O'Brien, "This is what I can't figure out. She said when she got married, she was a virgin."
Visibly surprised, O'Brien responded, "She told you that on the radio?" Stern confirmed, "Yes." He then played a clip from Kudrow's previous appearance on his show, where Stern questioned Lisa that she could have been Mrs. O'Brien; was it the sex that ruined it? To which Kudrow responded, "It's not true really; I had a huge crush on him, and it's like, you know, when you are friends with someone, you think this is the best relationship you can ever have in your life, but it's not true; sometimes you are just supposed to be friends."
Turning back to O'Brien, Stern and his co-host inquired, "So, what's the deal?" With a humorous manner, O'Brien quipped, "I'm impotent." Stern, not the one to let go that easy, said, "No, you are not!" O'Brien further joked, "I tried several times, but I just couldn't." Persisting, Stern asked, "Look, please, you had sex with her, right?" O'Brien looked uncomfortable and said, "Come on, Howard." Yet, maintaining his composure, he told Stern, "A gentleman doesn't tell tales." As the questioning grew more personal, O'Brien deflected with, "I'm a very religious Catholic," adding, "I don't believe in premarital sex."
However, this is not the first time Stern has made a guest uncomfortable on his show. In an interview with Anna Nicole Smith in 2002, Stern apparently body-shamed the actress as he called her a "heavyset woman" and also persuaded her to weigh herself on air. In another interview with Emma Bunton, Stern's comments were perceived as sexist. He asked the 'Spice Girl' star, "So, you've said in other interviews that you were 16 when you lost your virginity." To Bunton replied, "You've done research." Stern further added, "That's when you were Swallow Spice." Bunton replied in shock, "I really thought that you weren't gonna be this rude to me."