A Look At Macaulay Culkin’s Dating History

Macaulay Culkin met his ex-wife, Rachel Miner, at school when he was 14 years old. They had an on-again-off-again relationship until Culkin gave her an ultimatum — either they tie the knot or break things off for good. And as expected from teenagers, they chose the latter. “We dated four times before we got married,” he recalled in an interview with New York Magazine. “She’d broken up with me three times before, and so the last time we were going out I said, ‘Marry me now before you dump me again.’ What can I say? She was my girl.”

They tied the knot in 1998 when they were both 17, but predictably, it didn’t last long. The pair split just two years later, with a representative for Culkin telling the media that the separation had been amicable. Looking back, the actor recognized that they didn’t have a typical marriage, telling CNN’s Larry King that it ended because it simply ran its course. “Why doesn’t any marriage work,” he said. “You know, it just happened sometimes. You never want something like that to happen. And of course when we got married we thought we’d be together forever.”