The former flames met in the late '90s at Reese's 21st birthday party and were soon co-starring in the teen movie "Cruel Intentions." They tied the knot in 1999 but seven years and two kids later, they called it quits. "I was so, so young. I was, like, ridiculously young,” Reese told UK Elle in 2011. "I learned a lot, though. It was an excellent opportunity for me to really find out what it means to be a partner and to be in a marriage and it's not anything that I thought it was." She's since remarried, to agent Jim Toth, with whom she welcomed her third child in 2012.