Ben Affleck and Jennifer Lopez
In retrospect, it really doesn’t seem like there was any way for Ben Affleck and Jennifer Lopez to survive as a couple. Dubbed “Bennifer” by the press, Affleck and Lopez were opposites who had everyone paying attention—especially when he proposed with a $1.2 million, 6.1 carat pink diamond. They set the wedding date for September 14, 2003. The relationship caused even more frenzy when they starred in Gigli and gave an interview in a prime-time special with Diane Sawyer. But the movie bombed, and rumors seeped out about Affleck’s drinking and partying, and eventually he was accused of having a “wild night of sex” with a Canadian stripper at a party at Christian Slater’s house. The speculation was never confirmed, but the engagement was called off shortly thereafter. Both Lopez and Affleck said the relationship could never stand the constant media attention they were under. “I don’t think I’ve ever been heartbroken in that way before—had so many hopes and dreams on something,” Lopez said. “When you go through that kind of heartbreak in front of everybody, you are not quite the same person you were before.” Affleck, for his part, said they were “caught in the eye of the storm,” but later admitted the high-profile relationship—and breakup—was “probably bad for my career.” Affleck’s best friend, Matt Damon, later said Bennifer was “one of those weird situations where there was absolutely nothing you could do…all you could do is support [your friend] and talk shit about the people writing those things.” Despite all the pain, Affleck and Lopez seem to be doing fine now. Affleck married actress Jennifer Garner in 2005 and they have two daughters, Violet, 5, and Seraphina, 2. Lopez married singer Marc Anthony in 2004—only months after she and Affleck broke up—and now is the mother to twins Emme and Max, 3.