Giraldo had a tribal design tattoo on his left forearm that contained the number 525. He was reluctant to discuss its meaning. Comedian Jim Norton of "Opie and Anthony" later said that it represented his sobriety struggle; May 25 was the day that he first sobered up. Giraldo had been to rehab for alcohol and drug abuse several times. He said that once he had been so intoxicated that he punched something and broke four bones in his hand while performing at Gotham Comedy Club. Through the early 2000s, Giraldo was candid about his struggles with drug and alcohol addiction, and the challenges of life on the road, often incorporating these themes into his act. In 2009 he said that he had freed himself from addiction.