Did Kieran Culkin date Emma Stone? A Real Pain actor’s Dating history explored

Kieran Culkin is having a great year. He just starred in the critically acclaimed A Real Pain, and the awards season has blessed him resplendently. With the Academy Awards due on March 2, the actor has already won the Golden Globe, the SAG Award, the Critics Choice Award and the BAFTA, all for his supporting role in A Real Pain, which was directed by Culkin’s co-star, Jesse Eisenberg.

Culkin was well-received as Benji, the cousin of Eisenberg’s character, David, who reunites and takes a journey to Poland in honor of their grandmother. As Culkin is being appreciated in the awards circuit, his history with his ex-girlfriend, actress Emma Stone, has become a notable talking point. And it makes sense, after all, Kieran Culkin and Emma Stone used to be in a relationship back in 2010, and the two have come together professionally during the making of A Real Pain, which was produced by Emma Stone.

Kieran Culkin’s dating history

Kieran Culkin, who is a part of the famous Culkin family, appeared in the Home Alone series of films alongside his brother, Macaulay. In 2005, Culkin was in a relationship with New Zealand actress, Anna Paquin. The two appeared together on stage in the off-Broadway play, After Ashley, according to US Weekly. They were also a part of the cast of Broadway's The 24 Hour Plays in 2006. However, it is not clear when the relationship ended.

The Succession star was in a yearlong relationship with fellow actress Emma Stone. According to Vogue Magazine, the ex-couple ended the relationship in 2011 but maintained a close friendship. The two famously reunited during the Critics Choice Awards in 2024, where Stone was awarded the Best Actress award for her role in Poor Things. Culkin was also recognized at the ceremony for his role in Succession. The former couple was photographed hugging each other, seeming very much like old friends.

Kieran Culkin started dating his now-wife Jazz Charton in 2012. The Hollywood Reporter cleared the air around Culkin’s wife’s profession. Charton, who is from London, worked in an advertising agency, specifically in its music wing. Culkin was quoted in The Hollywood Reporter as he described his first encounter with Charton. Culkin noted her accent and reacted hilariously to her first name, Jazz. Culkin said,

“I said, ‘I’m Kieran. You have an English accent. What’s your name?’” he recounts. “She said, ‘Jazz.’ I said, ‘J-A-Z-Z, like the music?’ And she said, ‘Yeah.’ And I said, ‘Well, that’s f—ing stupid.’”

Culkin and Charton had an impromptu wedding during their road trip to Iowa in 2013. According to Charton’s Instagram post marking 7 years since the fact, the two married in the company of only 3 people while it rained. Adding a comic touch to her message, Charton wrote,

“Whose genius idea was it to have Father’s Day right before our anniversary? One gift counts for both right?”

Culkin is a father to two children. According to Cosmopolitan Magazine, their daughter, Kinsey Sioux, was born in 2019, and their son, Wilder Wolf, was born in 2021.

Kieran Culkin’s experience working on ex Emma Stone’s film

ScreenDaily reported in 2022 that Emma Stone was all set to produce Jesse Eisenberg helmed A Real Pain through her and her husband’s company, Fruit Tree. Kieran Culkin was roped in to star.

In an interview with Vogue Magazine, Culkin revealed that having Stone as the producer was really helpful for him. He had second thoughts about starring in the film, which was to be shot in Poland. He would be missing out on time with his family, and Stone put his mind at ease. Culkin said of Stone’s response,

“She goes, ‘If you don’t do it, the entire movie falls apart. But that’s not your responsibility. You shouldn’t feel that burden at all.’”

Continuing, Culkin said,

“She was nice enough to let me off the hook, so I guess I’m…in?”

Culkin explained that Stone had the idea of bringing his family for the first two weeks of production and ensured that Culkin traveled alongside Stone and her husband.

The production of A Real Pain brought two heavyweights of the industry, Kieran Culkin and Emma Stone, together, and we hope that the film shines bright during the awards season.