Dillingham was married in 1896 to actress and singer
Jennie Yeamans who was a former child star. She died in 1906. On May 5, 1913, in
Purchase, New York, he married Eileen Ann Kearney formerly of
Stillwater, Minnesota. The new Mrs. Dillingham was part of the
Alla Nazimova dance troupe and later was in several productions of Dillingham's. Dillingham bought his wife the
Barbara Rutherford Hatch House in 1920. The couple were regulars in society just as the old guard and the theater world began mingling. They were among the early snowbirds fleeing to
Palm Beach during the winter season. They were often at European social scenes such as the
Ascot and
Longchamp racecourses. The marriage broke up in August 1924 after Mrs. Dillingham became enamored of Julian Broome Livingston Allen, twelve years her junior, whom she married in October of that year. The divorce caused a sensation and was reported in Time magazine. Eileen was a lifelong friend of Florenz Ziegfeld's wife the actress
Billie Burke. She died in 1957 after divorcing her second husband in 1936, whom she had married twice. There have been various reports and rumors of Dillingham's
homosexuality including a longtime relationship with Charles Frohman, with whom he lived for some time between his marriages. His second wife's family believed theirs to be a marriage of convenience. He was a pall bearer at
Harry Houdini's funeral where he was thought to have quipped, "Let's see him get out of this one." Ill health and the
stock market crash of 1929 forced Dillingham to give up producing. The writer
Damon Runyon mentioned him in a short essay called ‘A Dog’s Best Friend’: “”Damon, what becomes of a man's friends when he gets sick?" I could not answer that one. It reminded me of a somewhat similar question asked by the once great theatrical producer, Charles Dillingham, at a time when he was broke and commencing to be forgotten along the big street, of which he was once one of the most glamorous and successful figures. He was sitting on a stool at a drugstore lunch counter when a gabby guy who knew who he was took the stool beside him and began babbling. "I wonder what's become of so-and-so?" he finally wondered, naming a Broadwayfarer who had sunk into obscurity. "I don't know", said Dillingham, adding thoughtfully, "I wonder what's become of Dillingham?"” Dillingham died of
bronchopneumonia on August 30, 1934, at the
Hotel Astor where he lived. ==Footnotes==