Kal Penn was just looking for a “nice guy” to date and wound up being set up with a pimp

Like most of us, Kal Penn’s first foray with dating in the gay world started off awkwardly.

While the Harold and Kumar Go To White Castle star didn’t publicly address his sexuality until 2021, he came out to family, friends and his manager many years earlier at the start of his career.

Finding himself in new territory, he sought some advice from his manager on how to maneuver dating while in the public eye, but somehow found himself being set up with a pimp. Don’t you just hate when that happens?

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Penn was also asked about President Obama’s previous opposition to same-sex marriage.

The 45-year-old opened up about the dating mishap during an appearance on SiriusXM’s Let’s Talk Off Camera with Kelly Ripa podcast and described the initial conversation that lead to the somewhat compromising position.

“Hey, I don’t know if this is ever gonna impact anything in work, but I’m just curious, how do actors meet nice people to date?” Penn said he asked his manager on the phone. “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?”

Since his manager wasn’t gay (red flag!), he had Penn meet up with a gay male “colleague” who he thought would offer better dating tips.

After connecting over sushi, Penn asked this colleague for help finding a “nice guy.”

“He goes, ‘Yeah, I mean, I’m just gonna email you a list just of some guys and their photos,'” Penn recalled. “And I’m like, ‘Whoa, that’s so cool! Playing matchmaker already.'”

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But then things went quickly in an entirely different direction.

“Yeah, and, you know, they’re not that expensive,” the man said. “And they’re never gonna say anything.” Okayyyy!

Now realizing exactly what is being proposed, Penn made it clear he wasn’t looking to hire prostitutes. Not that there’s anything wrong with that.

“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?'” Yes, we’d all really like to know that answer!

But the man had no guidance and responded, “I don’t know anything about all that.”

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It was while promoting his autobiography You Cannot Be Serious in 2021 that Penn first addressed his sexuality, disclosed he had a boyfriend of 11 years and that they were also engaged. Bam!

“I discovered my own sexuality relatively late in life compared to many other people,” the actor told People magazine at the time. “There’s no timeline on this stuff. People figure their sh*t out at different times in their lives, so I’m glad I did when I did.”

Penn first met his fiancé, Josh, after taking a break from Hollywood to work for the Obama administration as associate director of the White House Office of Public Engagement.

The couple, who remain very private and are rarely photographed together, have yet to tie the knot.

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While guest hosting The Daily Show last month, Penn touched on his extended engagement while interviewing President Biden and joked, “every auntie and uncle that I have is beyond disappointed that there hasn’t been a wedding yet.”

Penn recently appeared on American Horror Story: NYC and the horror film Smile. He’s also part of the voice cast of the upcoming animated film Jodie, a spinoff of ’90s MTV hit Daria.

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