Doolittle married Josephine "Joe" E. Daniels on December 24, 1917. At a dinner celebration after Jimmy Doolittle's first all-instrument flight in 1929, Josephine Doolittle asked her guests to sign her white damask tablecloth. Later, she embroidered the names in black. She continued this tradition, collecting hundreds of signatures from the aviation world. The tablecloth was donated to the Smithsonian Institution. Married for over 70 years, Josephine Doolittle died in 1988, five years before her husband.