Hollywood Stars, Brazilian Actress & Costume Designer — Robert Redford's Love Life in 30+ Photos

From a Utah bride to a Brazilian bombshell, a Swedish beauty, and his artist German soulmate — see the women who captured the Hollywood star's heart.

Robert Redford wasn't just magnetic on screen — he was every bit as irresistible in real life. With his tousled hair, soft-spoken confidence, and that unmistakable twinkle in his eye, the legendary actor left a trail of women who, to this day, speak of him with awe and affection.

From long-term loves to quiet flings and jaw-dropping rumors involving Hollywood royalty, the late star's love life reads like a who's who of iconic women — each with a story to tell and a moment captured in time.

Lola Van Wagenen (1958 – 1985)

In 1958, with only $300 in their pockets, Redford wed Lola Van Wagenen, a Mormon from Utah. The young couple later relocated to New York, where they faced poverty, tragedy, and grief.

"We lost our first child in 1959. It was very traumatic," the Hollywood star revealed. Despite their pain, they went on to welcome three more children — Shauna, David, and Amy.

Sadly, life didn't get easier. By the early 1980s, their once fiery romance had grown into something else — a deep friendship, and they separated on mutual terms.

"We still have great love, great affection, great friendship. It is wonderful, and I think we probably deserve credit for it because the kids are great, they came through it OK," Redford shared.

Sonia Braga (1987 – 1988)

Following his divorce from Van Wagenen in 1985, Redford entered a high-profile relationship with Brazilian bombshell Sonia Braga, who was 14 years younger than him. They met in 1987 on the set of "The Milagro Beanfield War" — Braga's first American film.

Soon, he became more than a co-star. In between takes, they strolled, talking about nature and Brazil. Following Redford's death, Braga paid tribute to him in a heartfelt Instagram post.

Although they had not seen each other for many years, she noted how certain memories would return while she photographed flowers in New York — quiet walks, rare blooms, and the smell of the earth.

Lena Olin (1990 – 1991)

In the early '90s, Redford had a love affair with Swedish actress Lena Olin. Though details about their relationship remain scarce, Olin's tribute years later spoke volumes about the impact he had on her life.

On September 16, 2020, she shared a brief but heartfelt message on Instagram that read, "An incredible man! You made such a difference! As an actor, director, producer and friend!"

Kathy O'Rear (1990 – 1995)

In the early to mid-1990s, Redford also dated Kathy O'Rear, a costume assistant 20 years his junior. However, their five-year relationship played out far from red carpets and headlines.

Sibylle Szaggars (2009 – 2025)

Redford's final and perhaps most profound love came not from Hollywood but from art. He met Sibylle Szaggars, a German-born painter, at Sundance in the late 1990s.

The connection was immediate, untouched by fame or expectation. "So it was a wonderful beginning of a relationship," the Hollywood icon said.

"Because it began as two human beings meeting each other and finding a connection as two human beings rather than being colored by success or whatever," he continued.

They later married in 2009, and he called her "a very special person," praising their shared creative spirit. "She's younger than I am, and European, which I like, so that's a whole new life," Redford also noted.

Rumored Romances – Natalie Wood

Rumors of a romance between Redford and Natalie Wood circulated during their time working together, fueled by what many saw as an undeniable connection.

According to her assistant, Howard Jeffrey, the actress "fell head over heels for Redford" during filming, despite knowing that "he not only looked like Jack Anderson, the all-American boy, but he lived like him as well."

Redford later acknowledged a deep attraction and a "closeness beyond friendship," but also noted the risks of getting romantically involved with co-stars.

Still, he cherished her, stating, "I loved Natalie's seriousness." Even after Wood married agent Richard Gregson, Redford remained close to her — he was her best man at the wedding — and their bond endured until her untimely death in 1981.

Barbra Streisand

According to author Robert Hofler, speculation around Redford's relationship with Barbra Streisand dates back to the '70s.

In his book, "The Way They Were: How Epic Battles and Bruised Egos Brought a Classic Hollywood Love Story to the Screen," he revealed that Redford was initially hesitant to take on the role opposite Streisand in "The Way We Were" in the early 1970s.

The actor was allegedly wary of her strong presence and the intensity of their on-screen dynamic. Furthermore, Hofler alleged that when it came time to film the love scene, Redford took no chances — reportedly wearing two jock straps "to protect himself" while Streisand donned a bikini.

Hofler further claimed that Streisand was "infatuated" and "mesmerized" by Redford, who was described in the book as resembling a "Ken doll."

Streisand has never confirmed a romance but has always spoken highly of Redford. "Bob is that rare combination — an intellectual cowboy, a charismatic star who is also one of the finest actors of his generation," she shared.

She also opened up about their close bond, revealing, "Bob and I were genuinely curious about each other, and I believe that's what comes across on screen."

Following his recent passing, the actress paid tribute to him on Instagram, calling every day on the set "exciting, intense and pure joy." "He was one of a kind," she wrote. "And I'm so grateful to have had the opportunity to work with him."

Jane Fonda

Another one of Redford's rumored romances was with Jane Fonda. However, the actress set the record straight on what really happened between them.

"Well, I was in love with him," she revealed. The pair shared the screen multiple times and, "I was always in love with Robert Redford. I made three films with him and nothing happened because I was married and he was married," Fonda stated.

Despite the ups and downs, the actress described Redford as "a very good person," though she acknowledged, without elaborating, that "he just has an issue with women."

Following Redford's passing, Fonda shared a heartfelt tribute on Instagram. Posting a photo from "Our Souls at Night" with co-star Iain Armitage, she wrote, "Thank you, dearest Bob, for all the pleasure you brought over the years. RIP."

From a tragic first love in New York City to a decades-long romance with a German artist who met him as just a man, not a movie star, Redford's relationships paint a picture of a man who loved deeply.