Letterman, 60, greeted Hilton – who was sporting a form-fitting black halter dress – with a warm hug, telling her she looked “better than ever” as she took a seat.
After welcoming her back to New York City (“I love New York – I was born here,” Hilton said), Letterman abruptly asked: “Uh, how’d you like being in jail?” Audience members gasped and laughed as Hilton, 26, paused for a few seconds before saying, “Not too much.”
(See a video of the appearance here.)
Letterman then observed, “You know what, they locked up your friend Nicole,” referring to Nicole Richie’s brief time in jail for a DUI.
About Hilton’s own experience behind bars, Letterman asked: “Tell us now looking back on that experience, what have we learned? What can you tell us?” Hilton shifted in her seat before answering, “Well, obviously it was a very traumatic experience, but I did it, so I feel like I can do anything now.”
After grilling her about the food – dinner, Hilton said, was normally “jail mystery meat” – Letterman kept going: “So what was it you did? Do you know what you did?” Obviously uncomfortable, Hilton stared at Letterman and laughed nervously. “It was something about driving with an invalid license, wasn’t it?” Letterman said. “Yeah,” Hilton answered.
After facing a continued barrage of jail-related questions, Hilton, who was on the show to promote her new fragrance Can-Can and her upcoming movie, Repo! The Genetic Opera, said, “I don’t really want to talk about it anymore.” But Letterman would not be swayed. “This is where you and I are different. Because this is all I want to talk about,” he said.
As Letterman continued to press, Hilton held up her hand: “I’m going on the next question. I’m over it.”
At one point a crowd member yelled, “I love you Paris!” which she answered by saying, “I love you too,” and blowing a kiss. Quipped Letterman, “Somebody you met in prison?” Hilton, blushing, shook her head no.
“There’s other stuff to talk about Dave,” Hilton said. “I didn’t come here to talk about this. That was a long time ago.”
Finally, after more than six minutes of grilling, Hilton said Letterman was making her “sad that I came here.” Trying to make amends, Letterman offered: “I’ll buy you a parakeet.”
Who’s turning 40? Which celebs are high school dropouts? What’s hot and definitely not in fall fashion? Check out PEOPLE’s new digital magazine now!