Harold & Kumar star Kal Penn says his manager set him up with a pimp after he came out

Harold & Kumar star Kal Penn says that early on in his acting career, his manager tried to set him up with a ‘pimp’ to find love.

Kal Penn is best known for starring in the Harold & Kumar comedy film series and his role in sitcom How I Met Your Mother, and also served under the Obama administration as principle associate director in the White House Office of Public Engagement.

Penn came out publicly in 2021 by announcing that he and his boyfriend of 11 years were engaged, while promoting his memoir You Can’t Be Serious.

Speaking to Kelly Ripa on the podcast Let’s Talk Off Camera on Wednesday (5 April), the actor revealed that he asked his manager to set him up early on in his career, before he had publicly announced his sexuality – but wires got hilariously crossed somewhere down the line.

“You know, I shared my story with my brother and my parents first. I was like, ‘Hey, super gay. Just FYI,'” Penn told Ripa, before revealing that he asked his manager how actors date. “Like how do you know that somebody that you’re dating wants to date you for you? Like what are the ground rules here, and is it any different?'”

This is where the story starts to go south, though Penn didn’t realise it at first.

“He goes, ‘Yeah, I mean, I’m just gonna email you a list just of some guys and their photos.’ And I’m like, ‘Whoa, that’s so cool! Playing matchmaker already,'” Penn explained. “And he goes, ‘Yeah, and, you know, they’re not that expensive, and they’re never gonna say anything.'”

Penn continued: “I was like, ‘Sorry, I think you don’t understand. No disrespect to sex workers, but that’s not what I’m looking for. My question to you is, how do I meet a nice guy, go on a couple of dates?’ And he goes, ‘I don’t know anything about all that.'”

At least he was being supportive!

Kal Penn met his husband Josh in Washington DC while they were both working at the White House under President Barack Obama.

Penn took their relationship public in an interview with People magazine, while promoting You Can’t Be Serious, which covers Penn’s upbringing, his career in TV, film and politics, and personal moments such as his first date with Josh.

Cardi B even offered to officiate his wedding.