Barbra Streisand and James Brolin's Relationship Timeline

Barbra Streisand and James Brolin were set up on a blind date in 1996 and wed two years later

After 25 years of marriage, Barbra Streisand and James Brolin's relationship is stronger than ever.

The iconic singer, actress and director and Brolin first met at a blind date dinner party in 1996, when Streisand was 54 and Brolin was 56. The pair, who each have children from previous marriages, wed two years later in a highly-anticipated backyard wedding at Streisand's home in Malibu.

"I can't tell you how lucky I am that this would happen to me so late in life," Brolin said in his wedding speech. "Every night is a new adventure. Sleeping is a waste of time. I can't wait to see her again in the morning."

Through the years, Streisand and Brolin have supported each other at various awards shows and movie premieres, all while putting each other and their ever-growing family first.

"By the way, 20 years in Hollywood is like, 50 years in Chicago, I always say," Streisand said of her marriage in a 2016 interview with Mario Lopez of Extra TV.

From attending State Dinners together to doting on their grandchildren, here's everything to know about Barbra Streisand and James Brolin's relationship.

July 1, 1996: Barbra Streisand and James Brolin get set up on a blind date

Streisand and Brolin's first meeting was at a dinner party with mutual friends, including Streisand's ex-boyfriend Jon Peters. "We were set up as a blind date, and I was so shy that I came into the house and I went downstairs to be with the children and play with them until I had to sit down at the table," Streisand said in a 2021 appearance on The Tonight Show.

She also revealed that she made fun of Brolin's haircut later that night. "I expected a guy with a brown beard and brown, wavy hair, like a mountain man," she joked. "And I saw a guy that had all his hair cut off, no beard. And I walked by him. I put my hand through his hair and said, 'Who f—ed up your hair?' "

September 1996: James Brolin heads to Ireland to direct My Brother's War

Three months after their first date, Brolin shipped off to Ireland to direct his political thriller My Brother's War.

Despite the distance, Streisand and Brolin stayed in touch. "I remember falling asleep on the bathroom floor with the phone pressed against my ear," she told PEOPLE in 1998.

November 7, 1996: Barbra Streisand opens up about meeting James Brolin

In an interview with the Los Angeles Times for her 1996 rom-com with Jeff Bridges, The Mirror Has Two Faces, Streisand opened up for the first time about her relationship with Brolin.

"I couldn't have met him while I was making this movie. I wouldn't have been open," she explained. "Once the movie was done and I could relax and edit the movie in my house, which is the fun part, I was open to a relationship again and it manifested itself."

November 10, 1996: Barbra Streisand and James Brolin make their red carpet debut

The couple made their red carpet debut at the Ziegfeld Theater for the New York City premiere of The Mirror Has Two Faces. Streisand starred in and directed the film, and also wrote the movie's original song, which earned her an Oscar nomination.

March 24, 1997: Barbra Streisand and James Brolin attend the 69th Academy Awards

Streisand and Brolin hit another red carpet together for the 1997 Oscars. At the ceremony, Céline Dion performed a rendition of Streisand's song from The Mirror Has Two Faces, "I Finally Found Someone."

July 1, 1998: Barbra Streisand and James Brolin wed in Los Angeles

Exactly two years after their first date, Streisand and Brolin tied the knot with a star-studded backyard wedding. Guests included John Travolta, Kelly Preston, Tom Hanks, Rita Wilson, Quincy Jones and Sydney Pollack. "We wanted to be surrounded by people we've loved for a long time," Streisand told PEOPLE.

At the reception, Streisand serenaded Brolin with two new love songs. "It was probably the most beautiful wedding I've been to," said Travolta.

August 27, 1998: Barbra Streisand supports James Brolin at his Hollywood Walk of Fame induction ceremony

On Aug. 27, 1998, Brolin was honored with his own star on the Hollywood Walk of Fame. Streisand supported her husband at the ceremony in their first public appearance as newlyweds.

December 20, 2000: Barbra Streisand and James Brolin attend the National Medal of Arts Award Dinner at the White House

In 2000, former President Bill Clinton awarded Streisand with the National Medal of Arts, the highest honor for achievement in the arts.

Following the ceremony, Streisand and Brolin headed to the White House for the awards dinner, where they dined with the President and other honorees.

January 14, 2003: Barbra Streisand and James Brolin walk the red carpet at the premiere of A Guy Thing

Streisand was on deck to support Brolin at the premiere of A Guy Thing, his film with Julia Stiles and Jason Lee. The couple walked hand-in-hand to Mann's Bruin Theater in Westwood, California, where the premiere took place.

December 16, 2004: James Brolin and Barbra Streisand attend the premiere of Meet the Fockers

Brolin supported Streisand at the L.A. premiere of the hit comedy Meet the Fockers, the sequel film to 2000s Meet the Parents. Streisand starred alongside Ben Stiller, Dustin Hoffman and Teri Polo in the film.

2006: Barbra Streisand and James Brolin snap a photo of their blended family

Following a concert during her 2006 tour, Streisand and Brolin posed for a photo showing off their blended family. The photo includes Brolin's son, Josh, his grandson, Trevor, and Streisand's son, Jason Gould, with ex-husband Elliott Gould.

July 28, 2007: Barbra Streisand is awarded the Légion d'Honneur

On July 28, 2007, Streisand was given yet another prestigious award, the Légion d'Honneur, the highest French order of merit.

Brolin was in attendance at The Elysee Palace In Paris as former French President Nicolas Sarkozy officially pinned Streisand.

December 7, 2008: Barbra Streisand receives Kennedy Center honors

The awards kept coming for Streisand, who was honored by the Kennedy Center in 2008.

Streisand and Brolin shared a cute moment on the red carpet before the gala, where stars like Queen Latifah, Beyoncé and Ne-Yo performed in Streisand's honor.

January 19, 2011: Barbra Streisand and James Brolin attend a State Dinner at the White House

Streisand and Brolin, who have always been friendly with political figures, were guests of honor at a 2011 State Dinner at the White House for former Chinese president Hu Jintao. The pair were invited by former President Barack Obama and First Lady Michelle Obama.

August 25, 2015: Barbra Streisand and James Brolin throw a star-studded house party

Streisand and Brolin turned their house into a red carpet in 2015 when they hosted a star-studded dinner party with guests like Lady Gaga, Travolta and Ryan Murphy. "A wonderful evening at home," Streisand captioned a photo of the group.

Gaga went on to star in the remake of Streisand's iconic film, A Star is Born, a decision Streisand felt was "the wrong idea."

November 5, 2015: James Brolin reveals he and Barbra Streisand have separate bank accounts

In a 2015 interview with HuffPost Live, Brolin revealed that he and Streisand keep their finances separate. "We bifurcated, and I love it that way," he said.

"This is my third marriage, and I know what trouble can come out of marriage, so I didn't want any reason that I would ever have to be either divorced or married again," he explained, adding, "And that was 20 years ago, so it works."

2016: James Brolin opens up about convincing Barbra Streisand to sing in I'll Be Home For Christmas

Brolin sat down with Harry Connick Jr. on his talk show, Harry, and revealed how he convinced Streisand to sing in his holiday film I'll Be Home For Christmas.

"That wasn't necessarily easily done because she's never lent any of her music to any television," he said. "One day at dinner I said, 'You know honey, what if? What if?' And I didn't get much back right then and then a couple of days later it's, 'Merry Christmas, here's your Christmas present.' "

July 2, 2018: Barbra Streisand and James Brolin celebrate their 20th wedding anniversary

In a sweet post for her husband on their 20th wedding anniversary, Streisand wrote, "Has it really been 22 years since our blind date? Married for 20 years. Happy anniversary honey," signing off with her nickname, "Bee."

Reflecting on the milestone with Entertainment Tonight, Brolin revealed that his secret to a healthy marriage is couples therapy. "I do believe in counseling if anybody ever has a problem in their marriage," he said. "Bring in a referee, talk it over, and I swear to you, it will dispel by the end of the session, each time."

November 7, 2018: Barbra Streisand and James Brolin celebrate the birth of their third grandchild

Brolin's son from his first marriage, Josh, welcomed daughter Westlyn Reign, his third child and his first with wife Kathryn Boyd, on Nov. 7, 2018. Streisand fulfilled her grandma duties before Westlyn was even born: "She is really into it and I love that she is into it," Josh told PEOPLE in June 2018. "I mean, it's like very typical Jewish grandmother who is saturated by this event. It's awesome."

Josh and Kathryn welcomed their second daughter, Chapel Grace, on Christmas Day 2020. Streisand often posts photos with her two young granddaughters.

July 1, 2020: Barbra Streisand and James Brolin celebrate 24 years together

Celebrating their 22nd wedding anniversary and 24th year together during the COVID-19 pandemic, Streisand posted a throwback photo from her and Brolin's wedding day. "There's no one I'd rather be locked up with than you honey — can't believe it's been 24 years together!" she wrote.

June 2, 2021: James Brolin says being stuck at home allowed him to fall in love with Barbra Streisand all over again

In a virtual appearance on The Talk, Brolin revealed that lockdown measures actually strengthened his relationship with Streisand.

"We, for a long time, were put out by COVID. And a lot of people, their marriages haven't gone well during these 15 months," he said. "We've literally fallen in love over this period of time, just being stuck together every day and making it work."

August 6, 2021: Barbra Streisand shares her secrets for a long marriage

While promoting her 2021 album Release Me 2, Streisand shared her marriage secrets with Variety.

"The secret is to listen carefully," she explained. "I think to be a good actor, you have to listen. To be a good person, you have to listen. To be a good marriage partner, you have to listen. Hear the other person. Agree to disagree."

June 14, 2022: James Brolin said he would be open to working with Barbra Streisand

Speaking to AARP magazine, Brolin said that he's hopeful he can one day work with Streisand on a project, with him as an actor and her as director.

"We had two projects we read out loud a couple times that she wanted to do. She wanted to direct both," he revealed. "I'm fine with it, but she keeps thinking I'm going to be a rascal to direct. I tell her, 'No, I'm putty in every director's hands.' "

September 2022: James Brolin shares the key to a strong relationship

Brolin shared the secret to his and Streisand's long-lasting romance with PEOPLE in September 2022.

"I think everybody needs to be a negotiator," he explained. "Everybody needs to have patience and know when to take a walk."

November 5, 2023: James Brolin and Barbara Streisand appear on CBS Sunday Morning

While talking with Gayle King on CBS Sunday Morning, Brolin revealed that he proposed to Streisand three times.

"She wasn't sure about this idea," he said, to which Streisand added: "I have to try them out for a least two years."

Brolin also shared that he was celibate for three years before meeting his now-wife.

"I had not had any interest in getting involved in a lousy situation," he told King.

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