The Sweet Reason Reese Witherspoon Reunited With Ex-Husband Ryan Phillippe

In the late 1990s and early 2000s, no one could get enough of Reese Witherspoon and Ryan Phillippe. After co-starring in the cult classic "Cruel Intentions," the two blondes proved they were beyond perfect together. By the time the film came out in March 1999, the "Big Little Lies" star and "I Know What You Did Last Summer" actor were already engaged, a milestone they announced in December 1998, according to USA Today.

Witherspoon and Phillippe had met the previous year on her 21st birthday. And it was the "Legally Blonde" star who made a pass at Phillippe. "I don't know what came over me — maybe the seven Midori sours — but I told him, 'I think you're my birthday present,'" she told Jane magazine in 1998. "He thought it was so flattering." Witherspoon and Phillippe married in 1999 and welcomed daughter Ava months later, USA Today noted. In October 2003, they added a son, Deacon, to the brood, CNN reported. 

The relationship wouldn't last much longer. In November 2006, Witherspoon filed for divorce from Phillippe, just days after announcing their separation in late October, according to People. Witherspoon has indicated youth may have played a role. "I got married when I was 23 ... sometimes it's good to know yourself [first]," she told ITV's "Lorraine" in 2017. But she had no regrets, saying,  "I would never change anything." 15 years may have passed, but that doesn't mean the former couple doesn't have reasons to reunite every once in a while.

Reese Witherspoon and Ryan Phillippe's son, Deacon, graduated from high school, and the actors held a rather professional ceremony in the backyard. "Homeschool graduation," Phillippe captioned a June 9 Instagram post. Phillippe included a snap of the three together and a clip from the solemn event, showing Deacon shaking hands with Phillippe and his friends Matt Sinn and Benjamin Massing all dressed in proper academic attire. "I played principal," Phillippe clarified. Deacon loved the tribute. "Best dad ever," he wrote in the comments section. 

Deacon walked around the swimming pool, where his cap landed after he tossed it up in the air. Witherspoon also marked the occasion on her Instagram, though she opted for a less humorous approach. "So proud of the thoughtful, talented, kind & generous young man you have become," she captioned the post. "You light up our hearts and make us proud everyday."

This isn't the first time Witherspoon and Phillippe reunited in recent months. In October, they celebrated Deacon's 18th birthday with a party that included a big cake, Phillippe showed on Instagram. "We are lucky to be your mom and dad. Love you, pup.. (I'd say we did pretty good @reesewitherspoon)," he wrote. Following their divorce, Witherspoon and Phillippe made it a point to prioritize their children. "You have to get to that point as a divorced parent, as any parent, where you're not putting yourself first," he told Entertainment Tonight in November 2016.