David Letterman and Uma Thurman
In the 1990s, David Letterman appeared to be flirting with Uma Thurman during an interview. He started out with lighthearted jokes but then moved on to asking her the ages of the men’s she’s dated. He then slipped his own age into the mix forcing her to laugh it off nervously while trying to change the subject. The whole situation made viewers die from second-hand embarrassment.