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The stars began dating shortly afterward, but their romance didn't last long; the Hollywood "It" couple split in 2009.
Witherspoon began dating Hollywood agent Jim Toth shortly after.
He's moved on with Saturday Night Live producer Lindsay Shookus.
And on Thursday, Ben Affleck was spotted with his new girlfriend for the first time while leaving their dinner date at Giorgio Baldi in Los Angeles.
The couple welcomed son Tennessee James Toth in the fall of 2012.
New mom Witherspoon kept busy, promoting her romantic comedy .
She and Ryan Phillippe announced their separation in October 2006 and divorced the following year.
In an interview with Charlie Rose in 2014, Witherspoon opened up about the dissolution of their marriage. You know, you can't really be very creative when you feel like your brain is scrambled eggs," she told Rose.
And while dresses and heels play a big role, sometimes a mid-week date asks for no more than some skinny jeans, a pair of ankle boots and an eye-catching top.
And while we don't know much about Lindsay Shookus, we do think she nailed this cool but casual style.
Reese Witherspoon was born Laura Jean Reese Witherspoon on March 22, 1976, in New Orleans, Louisiana.Tags: Adult Dating, affair dating, sex dating