5. Reese Witherspoon
Photo: jdeeringdavisAfter 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.
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