Who has Macaulay Culkin dated? Girlfriends List, Dating History

• Macaulay Carson Culkin is an American actor, musician and podcaster who rose to fame with his leading role as Kevin McCallister in the 'Home Alone' films
• He has 7 siblings, 2 of which have also followed his footsteps in the entertainment industry
• He began his career at age 4 and achieved remarkable success by his 13th birthday
• He was married to actress Rachel Miner at age 18, and later had a long-term relationship with Mila Kunis
• He is currently in a relationship with Disney star Brenda Song, with whom he recently welcomed a son, Dakota Song-Culkin

Macaulay Carson Culkin is an American actor, musician, and podcaster who rose to critical acclaim as a child actor in the early ‘90s, starring in the leading role as Kevin McCallister in the popular film ‘Home Alone’. Culkin reprised the role of Kevin repeatedly, becoming the star of the entire series of films and ultimately earning him regard as one of the Top 100 Child Stars in history.

Born on 26 August 1980, in New York City, Culkin began his acting career at the very young age of four, and through his impressive talent as an actor, achieved remarkable success long before his thirteenth birthday.

It comes as no surprise, considering that Culkin and many of his siblings inherited their acting talent from their father, Christopher Cornelius ‘Kit’ Culkin, a retired Broadway actor and producer.

Culkin’s father never married his mother, Patricia Bentrap, and continued to have children after Macaulay’s birth, who happened to be his fourth child. Macaulay had a total of seven siblings, namely Jennifer, Shane, Dakota, Kieran, Quinn, Christian, and the youngest, Rory.

Sadly, in 2000 the family experienced the loss of the eldest daughter, Jennifer, who passed away by means of an overdose, and in 2008, Dakota was claimed as the victim of a car accident. Nevertheless, both Kieran and Rory have sought fame and fortune following their father and brother’s footsteps, pursuing a career in entertainment.

Macaulay began his career by performing as part of the Bach Babies at the New York Philharmonic, and throughout the ‘80s, Culkin would make guest appearances in various shows, including supporting roles in the films ‘See You In The Morning’, and ‘Uncle Buck’.

In 1990, Macaulay would reunite with his ‘Uncle Buck’ co-star, John Candy, for the filming of his big breakthrough, ‘Home Alone’, his performance in the comedy earning him his first Golden Globe nomination, and landed him a Young Artist and an American Comedy award.

From there, Culkin would go on to star in numerous films that included ‘Getting Even With Dad’ and ‘The Good Son’, until he announced an hiatus from acting in 1994. He later returned to the screen in the sitcom ‘Will and Grace’, and starred in the 2003 film ‘Party Monster’. Culkin would star in movies in the years that followed, though he certainly turned it down a notch, only appearing in a few credits.

At some point, following his arrest in 2004, news broke suggesting that the child star had become addicted to various substances, eventually shown to include prescription drugs and marijuana. In 2018, Culkin launched a website and accompanying podcast called ‘Bunny Ears’ on which he parodies other celeb’s websites, such as Gwyneth Paltrow’s Goop.

Culkin is set to star in upcoming episodes of the popular show ‘American Horror Story’s tenth season, however, the biggest good news in the child star’s life, other than the fact that he recently turned forty, is that he became a father.

As much as that would surprise any of Culkin’s fans, they might be even more surprised to learn about the ‘Home Alone’ actor’s romantic past. Despite his early introduction to the spotlight, Culkin has kept his personal life exclusively private, maintaining enough secrecy throughout his life and career to keep the gossip tabloids ever guessing.

Although most of the details are excluded, some of the names in Culkin’s dating history would nonetheless spark some interest among his many fans who would wish to know.

A Meaningful Friendship

Although not exactly part of Cullkin’s dating history, it might be of interest to some mentioning Macaulay’s near life-long friendship with the king of pop, Michael Jackson.

Culkin met Jackson around the same time that he earned recognition for his role in ‘Home Alone’, and in 1991 appeared in Jackson’s music video for the hit song ‘Black or White’.

Unfortunately, their innocent friendship would become the subject of discussion and speculation during the mid-2000s, when Jackson was first tried on counts of child sexual abuse.

However, Culkin remained steadfast behind his pop singer friend, steadfastlyly claiming that the charges against Jackson were outrageous and inconceivable. When questioned about his friendship with Michael, Culkin testified that they were nothing more than good friends, and although he shared a bed with Michael, insisted that Jackson never attempted anything with him.

According to Culkin, he never saw anything remotely suggestive of child abuse, or even of any sexual nature, adding that he didn’t participate if the allegations were by some small chance true.

In September 2009, Culkin attended the late king of pop’s funeral and memorial service, paying his respects to a friend Culkin had known for nearly two decades. After Michael’s unfortunate passing, Culkin was appointed as the godfather of Jackson’s children, Paris, Prince and Michael Junior.

To this day, Culkin insists that Jackson was innocent, which gained some support from the outcome of Jackson’s trials, and continues to mourn the loss of his friend.

Married At Eighteen

When it comes to romance in the spotlight, Culkin is no stranger to the difficulties and strain posed by the influence of stardom. Culkin’s first public relationship could be considered his high school sweetheart romance, however, unlike most teens, Culkin’s love affair with the actress Rachel Miner played out in front of the eyes of the public.

In 2004 during a live interview with Larry King on his show ‘Larry King Live’, Culkin confirmed that he intended to keep his personal life as private as possible, and rarely share any details about his life with either the media or his many adoring fans.

Regardless, Culkin did discuss his childhood, rise to fame and eventual retirement from the film business at age fourteen, in his experimental biographic novel ‘Junior’. Unfortunately, those hoping to discover intimate details about the ‘Home Alone’ actor’s romantic life in the book will be up for disappointment, since it mainly discusses his professional life.

Though most of the details remain obscure, much of Culkin and Miner’s relationship made it into the archives of gossip publications. At the time, both Rachel and Macaulay turned eighteen, and both were considered to have achieved exceptional heights in their respective careers.

Although Culkin took a break from acting a couple of years prior, Rachel earned recognition as a soap opera star, portraying the role of Michelle Bauer in ‘Guiding Light’.

Macaulay Culkin

It remains unclear how or when exactly the couple met, but things between them became pretty serious. In 1998, after both turned the legal age, Culkin and Miner decided to get hitched and tie the knot. Unfortunately, their romance was not meant to last, and by 2000 the couple separated.

Neither Culkin nor Rachel ever announced any reason for their split, but assured their fans that they came to a mutual decision, and their separation was amicable, with their divorce finalised in 2002. According to most sources, Rachel and Macaulay stay good friends even to this day, and whatever happened between them seems to be long forgotten.

Considering that it happened nearly more than twenty years ago, it’s not surprising, though most of Culkin’s fans may have forgotten about his love for Rachel, especially since his most famous relationship was with the actress Mila Kunis.

A Stable Recovery

Following his split from ex-wife Rachel, it appeared as if Culkin entered a dark time in his life, which became evident two years later after being arrested for possession of prescription drugs and recreational narcotics. Fortunately for the ‘Richie Rich’ actor, he gained the meaningful friendship of whom many considered could become the next, and perhaps the most suited, Mrs Culkin.

In 2002, Macaulay met actress Mila Kunis, though their low-key relationship would have gossipers struggling to discover the details behind their introduction and continued friendship. With both Kunis and Culkin keeping their personal affairs extremely private, few details survived the many years they spent together.

However, Culkin’s relationship with Mila became both his longest lasting and most significant high-profile romance among his list of conquests. When they met, Mila was eighteen and Culkin had recently turned 21.

Many had high hopes that the relationship would blossom into something spectacular and significant, as the couple remained together for nearly a full ten years. However, in 2009, with both parties putting distance between each other, rumours of their separation quickly surfaced.

In 2006, Culkin moved to New York, while Kunis stayed behind in Los Angeles, California, hoping to reach glorious heights in her career. Although Culkin’s move was seen as a prediction of where their relationship would end, the couple held on for four more years, doing their best to make the long-distance relationship work, until in 2010, news of their separation reached the public, but it was already old news by then.

Kunis and Culkin had split months before Mila’s revealing interview. Years later, Mila confessed that she was the one who messed up their relationship, despite stating at the time of their separation that things between them ended amicably, and that they will remain friends.

In her statement, Mila questioned if the relationship would have been different if they met when they were older, and personally believes it could have become a significant romance in Hollywood history if she hadn’t made mistakes.

On the other hand, Culkin has held his peace about his relationship with Kunis, as he has about most of his romantic involvements.

Love In Paris

After his heartbreaking experience with Mila, Macaulay left the US, relocating to Paris, France, where he still resides. In 2013, after recovering from the sorrow of separating from Mila, Culkin again started dating, though like always, Macaulay kept his private life secret.

Nonetheless, Culkin went public and official with American singer and actress Jordan Lane Price, with irrefutable proof surfacing that certainly suggested that Culkin and Price had intentions with one another.

Sadly, their relationship would not last too long, coming to an end by 2017.

After four years together, fans again finally found hope that Culkin would one day settle down and start a family. Unfortunately, regardless of his fans’ hopes, Macaulay and Jordan could not see their relationship through to a more happy period.

Fortunately, it was not the last news to surface regarding Culkin’s romantic interests. After many wonderful but heartbreaking experiences, Culkin finally met the woman who became his firstborn’s mother.

A Song Of Love

In 2017, maintaining some interest in his acting career, Culkin accepted a role in the film ‘Changeland’, where he met Disney star Brenda Song on set. Best known for her role and producing credits in ‘The Suite Life of Zack and Cody’ and its ‘On Deck’ spin-off, who is often referred to as the Queen of Disney, Song quickly fell in love with her co-star, and it marked the beginning of a sweet romance.

The couple has been together since, though have kept their amorous affair as low-key as possible.

Macaulay Culkin

Celebrating their third anniversary, Song and Culkin opened up to ‘Esquire’ magazine about their love, having nothing but the kindest and sweetest things to say about each other.

Among his many other traits, Song especially fell in love with Culkin’s certainty about his self-image, and how he accepts and knows exactly who he wants to be. As Song stated, she finds such qualities and confidence in a man absolutely irresistible.

The couple also revealed to ‘Esquire’ that they were trying for a family. In 2021, the good news of Brenda’s pregnancy was celebrated by her and Macaulay’s loyal followers and fans, and in April, Song gave birth to their firstborn, a son they named Dakota Song-Culkin, after Macaulay’s late sister.

According to the most recent reports regarding Brenda and Macaulay’s romance, it seems the couple are in the clouds after embracing the joys of parenthood and couldn’t be any happier together.

Finally, after so many years and bad experiences, Culkin’s fans are only celebrating that he’s come upon the sentimental happiness that we hope life has in store for all of us.

Olivia Wilson

Olivia Wilson is currently a reporter for AffairPost based in London, United Kingdom. Prior to joining AffairPost in September 2018, she was a entertainment reporter. Olivia studied journalism at Cardiff University, graduating in 2010.

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