Macaulay Culkin fell for his first wife, Rachel Miner, at 14. When they divorced, he blamed himself. Macaulay also struggled after childhood stardom.

Later, he met Brenda Song in his late 30s and became a dad at 40. He and his fiancée are focused on their child and shared their plan for the future.

Macaulay Culkin, the lead in the famous “Home Alone” movies, had known stardom since he was very young. Growing up, it seemed like everyone knew his name and recognized his face. But Macaulay only paid attention to one girl back then.

The child star met Rachel Miner when he was 14. At the time, they were both attending the Professional Children’s School in New York. At first, Rachel didn’t take to the actor very well. That said, after the bad initial interaction, the two soon found their footing.

Rachel Miner and Macaulay Culkin attend the screening party for “Gia” on January 28, 1998 at the Equitable Center in New York City | Source: Getty Images

Macaulay and Rachel were part of the same large group of friends. The actor explained that, at the time, everyone in the group had their counterpart, and Rachel was his. The child star reminisced that she was his girl.

But, as the rough start should have suggested, their relationship wasn’t without its hiccups. Throughout their relationship, Rachel broke up with her famous boyfriend three times. Macaulay remembered when he eventually got her to marry him:

“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.'”

Rachel Miner and Macaulay Culkin at premiere of ‘Star Wars the Phantom Menace,’ New York, May 16, 1999 | Source: Getty Images

Rachel said yes, and the two had a small, inconspicuous wedding at a stone chapel in Connecticut on June 21, 1998.

The guest list consisted of only 60 people, and none of them were invited by printed invitations. Instead, the couple devised a sneaky treasure hunt to confuse the press.

Macaulay’s First Own Family

Macauly and Rachel settled in happily as a family. They were also very focused on their family. They would go to Macaulay’s mother’s house whenever they could to help with his younger siblings, Kieran, Quinn, Christian, and Rory.

Although the actor has dealt with his fears more recently, he hasn’t returned to the public life he once had.

The couple was also quite popular, and they were featured in a Sonic Youth music video. Besides that, they spent much time in their flat, watching movies and tending to the numerous stray cats that Macaulay seemed to attract.

Macaulay Culkin and Rachel Miner attend the premiere party for “Star Wars Episode I – The Phantom Menace” on May 16, 1999 at Mars 2112 in New York City | Source: Getty Images

Unfortunately, the couple’s newfound bliss would soon come to a dramatic end. Right before they could spend their first Christmas together, tragedy erupted in the form of a rampant electrical fire in the home of Macauly’s mom, Patricia Brentrup.

The fire had spread quickly and sadly killed four neighbors. Afterward, a lengthy legal battle ensued that involved not only Patricia but also Macaulay. The “Richie Rich” star explained the event:

“Two family friends basically broke down our front door and told us. I ran to the television and boom, there it was: the Culkin fire.

Of course, the picture they had was of a Christmas tree on fire, but it had nothing to do with a Christmas tree.”

Rachel Miner and Macaulay Culkin arriving for the Tony Awards at Radio City Music Hall, 1998 | Source: Getty Images

After the fire, the family got together for Christmas at Macaulay’s house. Although the entire ordeal was a tragedy, the family was glad to be together for the holiday.

However, a few years later, Macaulay’s own little family was torn apart, and he blamed himself.

A Bitter Ending

In early 2000, Macaulay and Rachel made public that they were separating. Macaulay has always been noticed in public and, in a few instances, almost harassed by fans.

The effects of the attention slowly culminated over the years and left the actor incapable of leaving his house.

Although the actor has dealt with his fears more recently, he hasn’t returned to the public life he once had. Rumors surrounding alleged and disproved drug abuse also spurred on his isolation.

The “My Girl” actor opened up about his failed marriage:

“I had to learn to talk and how to communicate, and I should’ve done it more.”

Macaulay Culkin attends A Work in Progress – An Evening with David O. Russell at the Museum of Modern Art on April 10, 2002 in New York City | Source: Getty Images

Unlike so many child actors before him, Macaulay managed to avoid substance abuse and even only went to a club in his 20s.

He often said he felt like he had to avoid the usual pitfalls of fame because so many people expected him to fit into the stereotypical profile.

But one more thing could only fulfill his life even more. Macaulay wanted a baby.

Instead, Macaulay retracted from the world. He avoided the public’s gaze fervently, preferring the safety and privacy of his home.

Finally, after spending years out of the spotlight, he realized he needed to return to what he loved most. So, the actor started working again with the play “Madame Melville.”

Macaulay Culkin seen out in Manhattan on May 7, 2017 in New York City | Source: Getty Images

Along with many London critics, Macaulay expected himself to be terrible in his comeback performance.

Instead, the play was lauded, and his performance was praised as some of his best work. But, the actor still longed for a family of his own.

Finding Family at Forty

Macaulay’s return to the stage hadn’t brought him everything he wanted. He may have learned to be more at ease in public again, but he still lacked one thing he truly wanted. But that all changed on the set of “Changeland.”

In 2017, in Thailand, Macaulay starred in a movie directed by his friend, Seth Green.

Along with the “Party Monster” actor, Seth cast Brenda Song. When the two met on the set, they got along famously.

A little while later, they moved in together and adopted a few more pets. At that stage, he was happy:

“I mean, look at me: I got money, I got fame, I got a beautiful girlfriend and a beautiful house and beautiful animals.”

But one more thing could only fulfill his life even more. Macaulay wanted a baby. And soon after moving in together, Macaulay and Brenda were thrilled to hear that one was on its way.

On April 5, 2021, Brenda gave birth to a healthy boy named Dakota Song Culkin.

At the age of 40, Macaulay finally got everything he wanted. They decided to name their son after Macaulay’s sister, who passed away in 2008.

In true Macaulay fashion, the couple didn’t say much to the press except:

“We’re overjoyed.”

After the joy-filled birth of their first child, Macaulay knew it was the right time to make things official with Brenda.

Nine months after Dakota’s birth, the “Sweet Life of Zack & Cody” actress was wearing an engagement ring. They also said they definitely want Dakota to have siblings.