Pauly Shore, Kendra Wilkinson and Trey Songz all appear on Wednesday night's episode of "Kocktails with Khloe" -- where the former MTV VJ made it pretty uncomfortable by asking some very personal questions.
First, the "Bio-dome" star asked Khloe Kardashian why all the Kardashian ladies "date black dudes."
After being told by the host that the question was "racist," he clarified his remarks. "I think most of America's curious, not in a bad way, because a lot of guys want to have sex with you and they're like, 'F--k, I'm not black, I can't hook up with her.' You guys are hot as f--k."
He then tried to prove his point by highlighting Kim Kardashian's marriage to Kanye West, as well as Khloe's with estranged hubby Lamar Odom.
Shore pressed on -- asking if Khloe was still with Lamar ... and she was surprisingly candid about the current state of their relationship.
"I haven't been sexually ... I haven't kissed Lamar in years," she exclaimed. "Do I love Lamar and want the best for Lamar? 100%."
In another sneak peek at this same moment, Khloe confirms Pauly's beliefs.
"I'm not their vagina so all I can speak about is my vagina," she said, referring to who her sisters may date. "It's all I know though, I've never seen a white penis."
"So if you want to show me yours, I'd like to see it. I've never seen one that color," she added.
Hopefully, he doesn't do it.
Later in the show, Khloe attempts to talk about Caitlyn Jenner wanting to visit Lamar in the hospital ... where Shore just wouldn't stop interrupting.
"When he had his accident and was in the hospital, Caitlyn was like, 'I want to come and see Lamar,'" Khloe explained.
"You don't think Bruce would have? I'm just being straight. I'm being straight," Pauly interjects, before an awkward silence takes over the table.
Kardashian goes on to explain that Lamar didn't know about Caitlyn's transition before his coma, and that if Caitlyn were to visit, it would be the first time he'd see her.
"Imagine that! That is awesome," adds Pauly. "That would really freak him out! This is why you have the number one show!"
Shore isn't the only one bringing the awkward though.
In another clip, Khloe asks Kendra whether she and Hank will tell their children about his transgressions with a transgender model.
"We're trying to beat all this to the punch and teach our kids who we are and show them love and happy parents and be as open as we can," she replies, not exactly answering the question.
"I'm a free spirit. I walk around naked," she continues. "So I'm gonna teach free spirit stuff to my kids. To each their own. If you're not harming someone, not doing any hard to yourself, be the person you want to be. Be true to yourself. We have a job to help each other. Care for each other. If someone needs their help, you better stick it out with them."
So, there's that.
See more from these crazy kids when "Kocktails with Khloe" airs Wednesday, March 30 at 10pm ET/PT on FYI.