From Child Star To Family Man: A Complete Look At Who Macaulay Culkin Has Dated

Macaulay Culkin, the iconic child star whose face defined the 1990s, has navigated a complicated public life, but his romantic journey has quietly settled into a loving partnership. As of December 2025, the actor is happily engaged to actress Brenda Song, with whom he shares two children, marking a stable and private chapter in his life after years of high-profile, intense relationships that captivated the media.

The transition from a globally recognizable child actor to a private adult has been challenging, but Culkin has found lasting love and stability. This article dives deep into the complete dating history of the *Home Alone* star, exploring the key women who have been part of his life and detailing his current, thriving family life.

Macaulay Carson Culkin: Biography and Profile

Macaulay Carson Culkin is an American actor, musician, and podcaster, widely regarded as one of the most successful child actors of the 1990s. His career trajectory is unique, marked by unprecedented early fame followed by a deliberate withdrawal from the spotlight and a subsequent, measured return.

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• Full Name: Macaulay Carson Culkin
• Born: August 26, 1980
• Birthplace: New York City, New York, U.S.
• Age: 45 (as of the current date)
• Parents: Patricia Brentrup and Christopher "Kit" Culkin
• Siblings: Shane, Dakota (deceased), Kieran, Quinn, Christian, and Rory Culkin (all actors)
• Notable Roles: Kevin McCallister in *Home Alone* (1990) and *Home Alone 2: Lost in New York* (1992), Thomas J. Sennett in *My Girl* (1991), and Richard Tyler in *The Pagemaster* (1994).
• Accolades: Nominated for a Golden Globe Award for Best Actor – Motion Picture Musical or Comedy for *Home Alone*.
• Other Work: Co-founder of the comedy rock band The Pizza Underground, and creator of the satirical lifestyle website and podcast Bunny Ears.
• Current Partner: Brenda Song (engaged)
• Children: Two sons (born 2021 and 2023)

The High-Profile Relationships That Shaped His Adult Life

Macaulay Culkin’s dating life has been characterized by long-term commitments, beginning at a young age and continuing through his transition into adulthood. Each relationship provided a different type of public and private experience, often under intense media scrutiny.

1. Rachel Miner: The Young Marriage (1998–2002)

Culkin’s first significant relationship was with actress Rachel Miner. The pair met in 1996 and, in a move that shocked many given their young age, married in 1998 at the age of 18.

The marriage occurred during a period when Culkin was largely out of the public eye, having taken a hiatus from acting following his explosive child stardom. The union lasted four years, with the couple separating in 2000 and officially divorcing in 2002. Rachel Miner, known for her work in films like *Bully* and the TV series *Supernatural*, has maintained a relatively private life, similar to Culkin, since their split.

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2. Mila Kunis: The Nine-Year Romance (2003–2012)

Perhaps Culkin’s most famous and longest-lasting relationship was with actress Mila Kunis. The two began dating in 2003, shortly after his divorce from Rachel Miner was finalized. Their relationship spanned nearly a decade, ending in 2012.

The romance was notable for its longevity, especially within the volatile landscape of Hollywood relationships. During this time, Kunis’s career was on the ascent, particularly after her role in *Forgetting Sarah Marshall* and later *Black Swan*. Despite their high profiles, they managed to keep their private life largely out of the tabloids, a feat Culkin often attributed to his experience with fame.

Mila Kunis has since described the breakup as "a horrible, horrible breakup," although she later took responsibility for how she handled the split, maintaining that Culkin was a "huge, significant part" of her life. The separation marked a major turning point for both actors. Kunis went on to marry her *That ‘70s Show* co-star Ashton Kutcher, while Culkin continued his journey toward a more stable and less public existence.

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3. Jordan Lane Price: The Transitional Period (2013–2017)

Following his split from Mila Kunis, Macaulay Culkin was linked to model and actress Jordan Lane Price. Their relationship reportedly began around 2013 and lasted until 2017.

This period was less publicized than his previous long-term relationship. Price, known for her roles in soap operas and independent projects, provided a quiet companionship. While details of their time together are scarce, this relationship served as a bridge before Culkin met his current partner, indicating a continuous desire for commitment and stability in his personal life.

The Present: Engaged to Brenda Song and Life as a Father

Macaulay Culkin’s current relationship with actress Brenda Song represents his most grounded and family-focused chapter yet. The couple’s love story is a testament to finding peace and happiness away from the chaos of early fame.

Meeting on Set and the Path to Engagement

Culkin and Song first met in 2014 on the set of the film *Changeland*, which was directed by their mutual friend, Seth Green. They began dating officially in September 2017, after filming in Thailand.

Brenda Song, a former Disney Channel star known for her role as London Tipton on *The Suite Life of Zack & Cody*, shares a unique understanding of Culkin's experience as a successful child actor. This shared background is often cited as a key factor in their strong connection.

Their relationship quickly became serious, with Culkin openly discussing his desire to start a family with Song. He referred to her as "The Lady" and spoke about their comfortable, stable life together.

Parenthood and Private Family Life (2021–2023)

The couple welcomed their first child, a son named Dakota Song Culkin, in April 2021. The name was a touching tribute to Culkin’s late sister, Dakota Culkin. This announcement brought an outpouring of public support, celebrating the actor's newfound joy in fatherhood.

In early 2022, news broke that the couple was engaged, with Brenda Song spotted wearing a diamond ring. They have since maintained a very private family life, choosing to raise their children largely out of the Hollywood spotlight.

The family grew again in 2023 with the birth of their second son, further solidifying their commitment and stable home environment. Culkin has often expressed profound happiness, noting that he is finally a "home alone" no more, having built a loving family with his fiancée, Brenda Song. Their relationship is a powerful example of two former child stars finding a quiet, meaningful life together, focusing on their children and their supportive partnership.

Topical Entities and LSI Keywords

The story of Macaulay Culkin’s dating life is interwoven with his career and personal growth. Key entities and LSI keywords that define this narrative include: child actor legacy, *Home Alone* franchise, Kevin McCallister, *Changeland* production, Seth Green's friendship, The Pizza Underground band, New York City life, Kieran Culkin's career, Dakota Culkin tribute, former Disney star, high-profile breakups, and the transition to fatherhood.