5. Reese Witherspoon
After divorcing actor and Cruel Intentions costar Ryan Philippe, Reese Witherspoon tested the waters with other big Hollywood names, including Jake Gyllenhaal, before she met talent agent Jim Toth at a party. According to Witherspoon, Toth came over to save her from a friend of his, who’d had too much to drink and was making a fool of himself. In the ultimate wing-man move, Jim smoothed things over, and then landed himself a date with the skeptical star. Today, they are happily married.