Brenda Song calls romance with Macaulay Culkin her ‘longest fling ever’

Brenda Song is reflecting on her long-term relationship with fiancé Macaulay Culkin, revealing that what began as a casual “crush” quickly evolved into a serious, years-long partnership.

Speaking on Live with Kelly and Mark, Song recalled meeting Culkin years before they began dating, saying the two first connected while working on the 2019 film Changeland.

At the time, she described him as a close friend before realizing her feelings had shifted.

“I was like, ‘Oh, I think I have a crush on him,’” Song said, adding that she initially viewed the relationship as a lighthearted “fling” during filming.

Friends even encouraged her at the time, telling her Culkin would be a “safe” person for a casual romance. Song joked that she embraced the idea, calling it her “first fling.”

However, what she expected to be temporary soon turned into something much more lasting. “My fling turned into a nine-year relationship, two kids,” she said, adding with humor that it became “the longest fling of my life.”

The couple began dating in 2017 after reconnecting following their initial meeting in 2014.

They welcomed their first son, Dakota, in 2021, followed by their second son, Carson, in 2022. Culkin later proposed in 2022, though the pair have not yet officially married.

Song also shared insight into Culkin’s continued involvement in her professional life, noting his enthusiasm for her Netflix series Running Point.

She said he frequently pitches ideas for the show and enjoys discussing character storylines with the production team.

“He loves it,” Song said, adding that Culkin has even joked about appearing more in future seasons, continuing to brainstorm comedic cameos with the writers.

Despite their unexpected start, Song described their relationship as deeply grounded and full of humor, with the couple now balancing family life, work, and long-standing creative collaboration.