Kristin Chenoweth, the talented and vivacious actress, recently appeared on CONAN, the popular talk show hosted by Conan O’Brien. During her interview, O’Brien couldn’t resist delving into Chenoweth’s personal life, and the conversation took an unexpectedly hilarious turn.

Chenoweth, known for her lightheartedness, revealed that she has had her fair share of interesting encounters while out on dates. O’Brien playfully teased her about going on dates in the wild, spotting her in restaurants and even having her over to his house with a date. With a mischievous smile, he asked for her opinion on potential suitors, causing Chenoweth to admit that she often turns to O’Brien for dating advice.

The conversation quickly turned to the ups and downs of relationships. Chenoweth confessed that her personal life has been a bit bumpy lately, jokingly comparing it to a scene from a western with tumbleweeds rolling by. She explained that being constantly on the move for work makes it challenging to establish a stable relationship. However, she did mention that there is someone she currently has her eye on.

The talk took a hilarious twist when Chenoweth recounted a peculiar encounter with a previous boyfriend. Apparently, he had asked her if he could try on her pajama bottoms. Surprised, O’Brien couldn’t help but laugh and comment on the strangeness of the situation. Chenoweth further explained that it wasn’t a fetish; he simply wanted to relax and get out of his tight jeans while they were watching TV. She humorously concluded that the relationship didn’t last long after that incident, saying she didn’t want to date someone who felt the need to try on her clothes.

As if one peculiar ex wasn’t enough, Chenoweth shared another comical story. She recalled being on vacation in Puerto Rico with her father when her then-boyfriend decided to surprise her. To her surprise, he appeared jogging towards her on the beach, wearing nothing but a tight speedo. Chenoweth jokingly confessed that she had always found speedos unattractive, and this encounter only solidified her opinion. Needless to say, that relationship didn’t last either.

O’Brien, always quick with wit, chimed in, suggesting that Chenoweth might have better luck finding a suitable partner through her show. Chenoweth comically responded by mentioning that she often receives prison mail, where inmates express their admiration for her. She jokingly added that perhaps she should start saving the letters and read them on the show.

Kristin Chenoweth‘s appearance on CONAN provided viewers with a glimpse into her amusing dating experiences. As always, the talk show provided a lighthearted and entertaining platform for celebrities to share their anecdotes and engage in playful banter with Conan O’Brien.