David Letterman, 75, Admits He’s Devastated After Son Harry, 18, Goes Off To College

In a rare appearance on 'Jimmy Kimmel Live,' David Letterman reflected on the heartbreak of his teenage son, Harry, leaving home to start his life at college.

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“They tell me he’s in college,” said David Letterman when joking about his son, Harry, during an appearance on the Sept. 28 episode of Jimmy Kimmel Live! During this rare return to late-night television, David, 75, spoke about his feelings after his 18-year-old son began college. “The separation of the kid leaving home, I thought it would be nothing, but it’s devastating,” said Letterman. “Am I the only one that feels that way?” he asked the audience, which responded with sympathy for the late-night icon.

“He’s been gone a month today,” added Letterman, who later said that he texts his son now and then. “I got a text from him today. I know everyone goes through this, and forgive me if I’m sounding a little over-emotional about this situation. Well, he texted me today and said, ‘Guess what? No classes.’ And right away, I think, ‘Well, I’m getting my money’s worth today.’ I text back, ‘Go out and have some fun.’ ‘Okay.’… and then I add, ‘take pictures.’ And he texts back, ‘of what?’ And I said, ‘of cool things you see on your day off from college.'” A few minutes later, Harry sent a photo of “two old people having lunch,” which had David laughing. “Let’s pump the breaks on all this fun we’re having at fun, fer gods sake. Easy does it, buddy.”

avid Letterman, center, his wife Regina Lasko, right, and son Harry tour outside the John F. Kennedy Library in Boston (Shutterstock)

“We had a truckload of crap to take up to his room and his room man, it’s not as big as [Jimmy Kimmel‘s] desk.” From there, David relayed a story of moving Harry into his dorm. After finding parking “several acres away,” Dave said that it was “ninety-six degrees, and then the kid and I carry a sofa up three flights of stairs.” When Jimmy asked if this story was true, David laughed. “No. Does this stuff have to be true?”

David also said he called his son a week into college to check up on him. “I said, ‘Harry, have you met the kid yet that sells weed?’ I’m thinking this would get a good laugh. Harry says, ‘I cannot confirm or deny.'”


Harry is the son of the late-night legend and Regina Lasko. Regina, 61, and David began dating in the late 1990s, and they welcomed their son in 2003. “I could never imagine ever being a part of something that turned out this beautiful,” David said in an episode of The Late Show, per CBS. Harry is David’s only child and is named after Letterman’s late father, Harry Joseph Letterman. “So God bless dad, and God bless Harry,” Letterman said in 2003, basking in the glow of fatherhood.