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  1. Sep 28, 2022 · the television icon joked about asking his son, Harry, during a phone call. David Letterman is opening up about becoming an empty nester! On Jimmy Kimmel Live Tuesday, the legendary...

  2. Sep 28, 2022 · David Letterman is sharing his experience of recently becoming an empty nester. Letterman, 75, was a guest on Tuesday night’s "Jimmy Kimmel Live," during which he cracked a joke about his...

    • Janelle Ash
    • 2 min
  3. Sep 27, 2022 · David Letterman on Jimmy's Obsession, Relationship with Howard Stern and His Son Going to College. Dave talks about his son Harry going to college, being an empty nester now, Jimmy being on Monday Night Football, being intimidated by Howard Stern when they first met, their friendship now, Howard sending him a watercolor he painted, his viral ...

    • 17 min
  4. Jul 22, 2023 · 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.

  5. Nov 29, 2023 · David and Regina welcomed their son Harry on Nov. 3, 2003, in New York. David announced his sons birth on his late-night talk show and told the audience, “I could never imagine ever being a...

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  6. Nov 21, 2023 · David Lettermans Life as an Empty Nester: “I Spend a Lot of Time Googling Symptoms”. Stephen Colbert and David Letterman compare notes as loving fathers who have endured the pain of...

    • 5 min
    • 489K
    • The Late Show with Stephen Colbert
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  8. Dave talks about his son Harry going to college, being an empty nester now, Jimmy being on Monday Night Football, being intimidated by Howard Stern when they first met, their friendship now,...

    • 17 min
    • 1.2M
    • Jimmy Kimmel Live