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10) Reese Witherspoon and Ryan Phillippe
Cruel Intentions stars Ryan Phillippe and Reese Witherspoon were the "It" couple of Hollywood; after dating for two years, the pair got married in 1999. The couple share two children together, Deacon and Ava.
After the couple officially separated in 2007, the tabloids were busy running their heartbreaking break-up story over and over again. In an old interview with Larry King, Witherspoon went candid and opened up about her difficult breakup with ex Phillippe. She said:
"I think more of the problem was age,...When we got together we were so young. I think it can create issues with two people in this industry because there's so much noise that goes along with it."
In 2011, Witherspoon got married to Jim Toth, but the two split recently in 2023. Meanwhile, Phillippe did not marry since then.
11) Demi Lovato and Wilmer Valderrama
Wilmer Valderrama and singer Demi Lovato were another couple, who had their relationship widely covered by the media, who observed every move of the couple. As per Insider, the two began their romance back in 2010 after meeting at a Voto Latino public service declaration event that was held to encourage people to vote.
Insider also reported that the singer Lovato disclosed that Valderrama was a huge part of her recovery procedure from bipolar disorder, eating disorder and self-harming. Their relationship looked quite promising as shown in the media. However, in 2016, the pair ended their almost six-year-long relationship. After their breakup, both celebrities took to Instagram to share the post, which read:
"This was an incredibly difficult decision for both of us, but we have realized more than anything that we are better as best friends,...We will always be supportive of one another. Thank you to everyone who has offered us kindness and support over the years. With only love, Wilmer & Demi."
12) Fergie and Josh Duhamel
Josh Duhamel and Fergie calling it quits in 2017, after their nearly eight-year-long married life, was one of the worst celebrity breakups of all time as they were one of the most fan-favorite couples in the entertainment industry. In September 2017, the celebrity pair went on to confirm their breakup through a joint statement they gave to People. In the statement, they wrote:
"With absolute love and respect we decided to separate as a couple earlier this year,...To give our family the best opportunity to adjust, we wanted to keep this a private matter before sharing it with the public. We are and will always be united in our support of each other and our family."
The singer Fergie, later on, revealed that the two have been successfully co-parenting Axl, their son. As per Insider, in an interview actor, Duhamel opened up about the two o-parenting their son. He said:
"...going really well....All we want is the best for our son, so it's a bit of a juggling act but we're both grown ups who can handle a lot,...And he's happy. That's the main thing."
