Loving became friends with Long Branch owner Chalkey Beeson, and become associated with several notable gunmen, gamblers and lawmen of the day, including Doc Holliday, Wyatt Earp, Bat Masterson, John Allen, as well as Levi Richardson.

The two threw taunts back and forth for a time, but with nothing more than verbal confrontations until March of that year, when the two became involved in a fist fight on Front Street.

After exchanging punches, Richardson threatened, "I'll blow the guts out of you, you cockeyed son of a bitch."

Suddenly, Richardson said loudly "You wouldn't fight anything, you damned son of a bitch," to which Loving said calmly, "Try me and see."

The Globe newspaper said of the fight; "...it seemed strange that Loving was not hit, except for a slight scratch on the hand, as the two men were so close together that their pistols almost touched each other..."[citation needed]