Hugh Grant and Elizabeth Hurley: Hugh and Elizabeth were together for 13 years. However, when Grant was arrested in 1995 for soliciting a prostitute in Los Angeles, his relationship with Hurley, the Estee Lauder model, slowly began to crumble as Hugh admitted on The Tonight Show with Jay Leno that he had done a “very bad thing”. The English lovebirds finally called in quits in 1998, but today, remain close friends and Grant is the godfather to Elizabeth’s son Damian.
The GOOP founder tried setting up Taylor Swift with Jake Gyllenhaal. If you're wondering how that turned out, you may want to tune in to "We Are Never Ever Getting Back Together."
Credit: Kim Kardashian and Kris Humphries' televised wedding