Ryan Phillippe married fellow actress Reese Witherspoon back in 1999 when they were both in their early 20’s. The young couple had two children together but apparently Phillippe was looking for some fun outside of the marriage and hardly hid his antics. Paparazzi caught the Cruel Intentions actor and his fellow Stop-Loss co-star Abby Cornish out numerous times together coupled up at restaurants. The duo was even busted leaving his apartment together. Witherspoon and Phillippe divorced in 2007.