8. Cute or Creepy? Jackson surprised his now-wife as she drove away.

Alan Jackson wanted to talk to the woman who would later become his wife, so he tried to impress her by flipping a penny down her shirt and asking if he could retrieve it. Then he hid in the back seat of her car outside of the Dairy Queen, and when she drove off, he popped up and surprised her. “I remember screaming and pulling over,” Denise told GAC. “When I got my breath a little bit, we rode around and talked, and the relationship started from there.” Well, in actuality, it took a little while. Denise said no to his first request for a date, but after he got a cooler car she gave in.