They have a son named Robert Lovering age 146.
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On 4 July 1878, Mudgett married Clara Lovering in Alton, New Hampshire; their son, Robert Lovering Mudgett, was born on February 3, 1880 in Loudon, New Hampshire (as an adult, Robert was to become a Certified Public Accountant, and served as City Manager of Orlando, Florida).
On January 28, 1887, while he was still married to Clara, Holmes married Myrta Belknap in Minneapolis, Minnesota; their daughter, Lucy Theodate Holmes, was born on July 4, 1889 in Englewood, Illinois (in adult life, Lucy was to become a public schoolteacher).
Holmes lived with Myrta and Lucy in Wilmette, Illinois, and spent most of his time in Chicago tending to business. He filed for divorce from Clara after marrying Myrta, but the divorce was never finalized.