A Look Back at Robert De Niro’s Dating History, From Naomi Campbell to Now

Diahnne Abbott (1975-1988)

Diahnne Abbott, an actress and singer, was Robert De Niro’s first wife and arguably his most significant early relationship. The pair met on the set of the 1976 film Taxi Driver, where Abbott had a small role as a concession girl. Their connection was instant, and they tied the knot that same year.

During their 12-year marriage, the couple welcomed a son, Raphael, born in 1976. De Niro also adopted Abbott’s daughter from a previous relationship, Drena. The family often appeared together at red carpet events, presenting a united front to the public.

However, as De Niro’s career continued to soar, rumors of infidelity began to surface. The couple’s relationship gradually deteriorated, leading to their divorce in 1988. Despite the split, both have maintained a cordial relationship for the sake of their children and grandchildren. His first grandchild, Leandro, was born in 2003. Tragically, in July 2023, Leandro’s mother, Drena, announced he had died at the age of 19 following a battle with addiction.

In an interview with People, De Niro expressed his grief, saying he felt “disbelief” when he heard the news about his first grandson. “It’s just a shock,” he said. “[I] never thought it would happen.” De Niro added, “And I just then started thinking about all the things I could have, should have done maybe with him. I don’t know if that would’ve made a difference. And so that’s always playing through my mind.”

De Niro and Abbott are also grandparents to son Raphael’s three children, whom he shares with ex-wife, Claudine De Matos.

Helena Springs (1979-1983)

While still married to Diahnne Abbott, De Niro reportedly had a long-term affair with Helena Springs, a backup singer who worked with music legends like David Bowie and Bette Midler. Their relationship, though never officially confirmed by De Niro, was an open secret in Hollywood circles.

Springs claimed that she and De Niro had a daughter together, Nina, born in 1982. While De Niro allegedly paid for the birth expenses, author Shawn Levy—who wrote the biography, De Niro: A Life—claims the actor wanted little to do with the child. “He drew the line at providing her with his medical history or a blood sample, fearing that she didn’t merely want to be able to fill in the gaps in the baby’s medical records, as she said, but rather that she was after more money,” Levy writes.

According to People, the situation led to a legal battle, with Springs fighting for child support and recognition. However, a court-ordered DNA test eventually proved De Niro was not, in fact, Nina’s father. While the court case was sorted, De Niro’s affair with Springs is still cited as one of the main factors that contributed to the breakdown of his marriage to Abbott.

Toukie Smith (1988-1996)

After his divorce from Abbott, De Niro found love again with actress and model Toukie Smith. While the couple never married, De Niro and Smith—known for her work on the NBC sitcom 227 and her modeling career—maintained a long-term relationship that lasted for nearly a decade. The pair did, however, split for a brief time in 1994, according to a profile in the New Yorker, before getting back together.

In 1995, De Niro and Smith welcomed twin sons, Julian Henry and Aaron Kendrick, via surrogate. The birth of the twins marked a new chapter in De Niro’s life, deepening his role as a father and his connection with Smith. But despite their growing family, the couple’s relationship eventually ran its course. They separated for good in 1996, but have remained amicable co-parents to their sons.

Naomi Campbell (1993)

During his on-again, off-again relationship with Toukie Smith, rumors swirled about a brief fling between De Niro and supermodel Naomi Campbell. The relationship took place sometime in the ’90s, when Campbell was at the height of her modeling career and De Niro was one of Hollywood’s most sought-after actors. While details about their relationship remain pretty scarce, the rumor mill went into overdrive when the two were spotted together at several high-profile events and intimate dinners.

Campbell, for her part, seemingly confirmed their romance in a 2020 interview. “Whatever they say about me, I have remained friends with all my exes … except the last one,” she told The Times. While she insisted “a lady never discusses the details of her private life,” she speak about her enduring “friendship” with De Niro. “I saw Robert De Niro just before lockdown,” she revealed at the time.

Grace Hightower (1997-2018)

Grace Hightower, a philanthropist and former flight attendant, became De Niro’s second wife in 1997. Their relationship was one of De Niro’s longest and most publicized, marked by ups and downs, separations, and reconciliations.

The couple met in 1987 at a London nightclub where Hightower was working. A decade later, they tied the knot in a star-studded ceremony. Their son, Elliot, was born in 1998, adding to De Niro’s growing brood.

However, their marriage hit a rough patch in 1999 when De Niro filed for divorce. The proceedings were never finalized, and the couple eventually reconciled, renewing their vows in 2004. In 2011, they welcomed their daughter, Helen Grace, via surrogate.

Despite their attempts to make the marriage work, De Niro and Hightower announced their final separation in 2018. De Niro confirmed the split in a statement, sharing that it was a “difficult” time for them both. “Grace and I have two beautiful children together. We are entering a period of transition in our relationship which is a difficult but constructive process,” he said. “I honor Grace as a wonderful mother and ask for privacy and respect from all as we proceed to develop our roles as partners in parenting.” Throughout it all, both have emphasized their commitment to co-parenting their children.

Tiffany Chen (2021-Present)

In his seventies, De Niro found love once again with Tiffany Chen, a martial arts instructor. The couple first met on the set of the 2015 film The Intern, where Chen served as De Niro’s tai chi instructor. However, their romantic relationship didn’t blossom until years later.

De Niro and Chen were first spotted together in 2021. Unlike some of his previous relationships, De Niro has been more open about his connection with Chen, appearing with her at public events and speaking fondly of her in interviews.

In April 2023, De Niro surprised many when he announced the birth of his seventh child, Gia Virginia Chen-De Niro, with Chen at the age of 79. During an appearance on The View in May 2024, De Niro gushed about his new daughter and his relationship with Chen. “Everything that I’m consumed with or worried about or this or that just goes away when I look at her. That in itself is wondrous,” he said of their baby girl.

“She has a very sweet kind of way of looking at you and just taking you in,” he continued. “They just look at you and take it in, so I don’t know where it’s gonna go with her later when she gets older, but she’s thinking and she’s observing everything and watching.” The father of seven added, “I want to be around for as long as I can to enjoy it, enjoy her.”