Jack Harlow Tells Nashville Crowd He Lost His Virginity 'Twice' Jack Harlow recently told a Nashville crowd he had lost his virginity, not once but twice. “I always tell people I lost it twice because when I was 18, and I graduated high school, somehow, some way, I landed this dime piece who was five or six years older than me,” Jack told the crowd. “She was like 23, 24 — it blew my mind because Nashville, you have to understand, at that point, I’d only f__k with girls I’ve seen in the halls.” Jack told the crowd he felt as if he was “in the big league” during his time with the older woman, “I remember I used to take this girl to my indoor soccer games, and she would pick me up and take me home to my homeboys. She was sitting there watching the game, and they’d be like, ‘Yo, who is that?’ I’d be like, ‘Oh her? Yeah, we have sex, you know, like I was feeling myself, and it’s true, we did.” Jack also said the girl helped him during their first couple of times having sex, explaining to him that he didn’t have to “go so fast.” What stands out about your first time?