The legendary late-night TV show host David Letterman opened up about feeling devastated after he sent his son Harry off to college and officially becoming an empty-nester during his appearance on Jimmy Kimmel Live.
He said that all reports indicated that Harry was doing okay. However, the transition wasn’t as easy and seamless as he thought it would be. He said, “I thought it would be nothing, but it’s devastating.” He then asked if he was the only one who felt that way.
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The big reason behind it was that, over the years, the two had maintained a very close relationship. In 2019, Letterman told Willie Geist of Sunday Today about always trying to be his son’s best friend.
Letterman said he knew he was getting old, and who knows how much longer he would be around. He also added that he feels the most secure when he is with his son.
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Thankfully, Harry stayed in touch with him over the first month, texting him occasionally. The host even shared that he got one that day, saying there were no classes which made him extra emotional. Afterward, he expressed feeling like he was getting his money’s worth right there, so it was all good.
That said, knowing Letterman, he wouldn’t pass up on a chance to make some hilarious quips. Of course, he didn’t disappoint. Later in the interview, he told Kimmel that a week into college, he called his son and asked him if he had already met the kid who sells weed. To which Harry replied, “I cannot confirm or deny.”
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Aside from conversations about missing his kid, the TV icon also talked about how he had to take Harry and his “truckload of crap” to school and lug a sofa all the way up three flights of stairs. Kimmel was surprised and asked Letterman if it was true, and he responded laughing, “Is that true? This stuff’s gotta be true?”
You can check out David Letterman’s whole interview about his son Harry in the video below.

