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(20 December 1979 - 1988) (divorced)
Vaughan and Lenora "Lenny" Bailey met in 1973 after one of Vaughan's performances with the Nightcrawlers at La Cucaracha, a nightclub in east Austin. Although moved by Vaughan's musical prowess, she was attracted to his charmingly modest personality. Double Trouble's song "Love Struck Baby", he said, was written about her, after claiming July 5 as their "love struck day". The couple was married on December 23, 1979, between sets at the Rome Inn in Austin, using pieces of wire for rings. Drummer, Chris Layton, described the ceremony as "spontaneous", saying, "It wasn't like there was invitations sent out or a certain group of people attended—it was just whoever was there was hanging around." Layton also said their marriage was "pretty excitable and passionate". The song "Pride and Joy" is also about her, as well as the instrumental "Lenny", after she thought "Pride and Joy" referred to a former girlfriend of Vaughan's.
Upon return to their home in Austin from touring, Vaughan found the house padlocked, electricity shut off, and Lenny nowhere to be found. Biographers Joe Nick Patoski and Bill Crawford wrote that she "squandered his road earnings on dope while running around with other men that one acquaintance glibly described as 'police characters.'" After she declined to visit Vaughan in treatment for substance abuse, he filed for divorce three months later. The case was settled out of court, with Lenny receiving alimony, plus $50,000 in cash and twenty-five percent of net royalties (excluding albums after Live Alive). Vaughan's manager attributes the demise of their marriage to "jealousy" and "unfaithfulness", and as a result, they were both brokenhearted.