Mila Kunis Said She “F---ed Up” Her Relationship With Macauley Culkin

Hollywood cuties Brenda Song and Macauley Culkin recently made headlines as the first couple to ever be featured on the cover of Cosmopolitan magazine.

Maybe your social media algorithm even showed you pictures and videos of the two enjoying a Los Angeles Lakers game together.

Inevitably, folks have begun searching for the pair's respective dating histories — the perks of being a celebrity and all. So let's get into Macauley's relationship history.

Every '90s kid is familiar with Culkin's acting credentials. Obviously, the classic holiday film written by John Hughes, where he acts opposite Joe Pesci and Daniel Stern, is what made him a highly sought-after child actor.

John Candy fans will probably remember the young talent from Uncle Buck, and other notable flicks he's starred in also helped establish Culkin as a '90s talent phenom. The tragic ending of My Girl still probably tugs at the heartstrings of viewers, and then there was his chilling turn as a kid psychopath The Good Son where he acted opposite Elijah Wood.

The Pagemaster was another major studio release Culkin was featured in, along with Richie Rich. But then, after a while, folks didn't see too much of the young star for a few years. He had a role in a Sonic Youth music video, and then there was 2003's Party Monster, another role that saw him playing against the sweet and wholesome kid-friendly image he developed when he was a child.

Culkin didn't just have an early start in his movie career, however (he was just 10 years old when it was released). He got married very early as well. At just 18 years old, he officially married Guiding Light actress Rachel Miner in 1998.

Newsweek reported on the couple's plans to marry from when they were 17 years old. In 2000, they separated, and in 2002, their divorce was finalized.

Then, in 2002, Culkin and That '70s Show star Mila Kunis began dating when he was 21 years old and she was 18. They weren't exactly in the public eye all that much (not like Bennifer levels of publicized romance).

The Forgetting Sarah Marshall actress did talk about their relationship with Women's Health in 2009, however, according to People. "We grew up together," she said. "You find a steady rock in your life and that's all you need. We have our ups and downs but work through them. I don't know if I met him at 27 if it would have been a different relationship."

Reports indicate that the two were together until 2010, but news officially broke out of their separation in 2011. In a candid talk with actor Dax Shepard, Kunis took the blame for the relationship ending the way it did. "Horrible, horrible breakup ... I f--ked up. I was an a-- in my twenties, and I'll be the first to admit it."

In 2013, People wrote that Culkin was tied to Jordan Lane Price, a singer and actress. Much like his time with Kunis, the pair kept their personal lives... personal. However, they were seen out spending Thanksgiving 2013 together in Paris.

Then, around 2017, Price and Culkin called it quits.

This is right around the time the Home Alone star played Ian in Changeland.

During filming, he developed a relationship with co-star Brenda Song. Entertainment Tonight broke the news that the two were out on a couple's date with the movie's director, Seth Green, and his spouse, Clare Grant.

In a 2020 interview with Esquire, Song gushed about her affection for Culkin: "People don’t realize how incredibly kind and loyal and sweet and smart he is. Truly what makes Mack so special is that he is so unapologetically Mack. He knows who he is, and he’s 100 percent OK with that. And that to me is an incredibly sexy quality. He’s worked really hard to be the person he is."

The outlet added that Song keeps a notebook where she jots down the funny things he says that continually cracks her up. In April of 2021, the couple welcomed their son Dakota into the world. And two years later, they announced that their second son, Carson, was born.