TIS,
JFK had a running but kidding around feud with a rather oldish woman reporter for, I think, one of the Wash DC papers.
He would always recognize her at every press conference, and he always responded to her question humorously or with a clever quip.
She wore very large hats, if I remember correctly, and her manner was unintentionally amusing.
Her name escapes me, but I'll see if I can come up with something on Google.