Holman took an interest in one fan, Zachary Smith Reynolds, a hobbyist aviator and heir to the R. J. Reynolds tobacco company. He was known to friends and family as just "Smith." They met in Baltimore, Maryland in April 1930 after he saw her perform in "The Little Show". He asked his friend Dwight Deere Wiman, the producer of the show, to introduce him to her. He pursued her around the world in his plane, and became known as "Smitty, the traveling bear" in Holman's friend group, referencing his pet-like devotion to following her around the world. Although Holman's friends didn't like Reynolds, finding him moody and difficult to talk to, they tolerated his presence, as he paid for the entourage's visits to New York speakeasies and nightclubs. The couple argued often and would occasionally descend into fights in front of Holman's circle of friends. Reynolds threatened suicide to Holman on multiple occasions; In a letter to her, written while on an aviation journey, he once wrote: "Darling Angel. I would gladly come home if you were not going on with the show. I'll gladly give up this trip or anything I have to devote all my time to you, if you would do the same for me. If I get to the point where I simply cannot stand it without you for another minute, well, there's the old Mauser with a few cartridges in it. I guess I've had my inning. It's time another team went to bat."