10. Sheryl Crow & Lance Armstrong: Granted, Lance didn’t plan it this way, but the timing was still pretty lousy. The famous cancer survivor broke off his engagement with rocker Sheryl shortly before her own diagnosis with breast cancer. While Lance pledged his support, the crisis failed to bring the couple back together. Sheryl recovered with treatment but confessed months later she was still brokenhearted.

9. Reese Witherspoon & Ryan Phillippe: Hollywood’s golden couple seemed so perfect together. But as soon as they announced their separation, Ryan was reported to have had a dalliance during filming with Aussie actress Abbie Cornish — among other on-set hotties.