Sandra Bullock has had her share of great loves, just like the characters in her charming romantic movies.
The Oscar winner seemed to find her lifelong match in Jesse James, whom she wed in July 2005. However, they divorced in June 2010 after multiple women came forward in March claiming they’d had affairs with James. He later admitted to the infidelity during a 2011 appearance on ABC News.
Bullock and James had begun the adoption process for son Louis in January 2010, but Bullock finished the process as a single parent after their split. She also went on to adopt daughter Laila in December 2015.
After becoming a mother, the actress moved on with Bryan Randall in 2015. Randall died at age 57 in August 2023 after a private three-year battle with ALS. News of his death came days after Us Weekly confirmed that he and Bullock were in a “cooling-off period” after spending time apart.
Scroll down to revisit Bullock’s dating history:
1 of 9
Tate Donovan
The Miss Congeniality star met the O.C. alum while filming 1992’s Love Potion No. 9. They dated for three years and were even engaged before calling it quits.
Bullock also formed a friendship with Jennifer Aniston because of their relationships with the actor. “We were introduced by our former boyfriend. I say ‘our’ because you and I both partook of this one human being,” she told the Friends alum in her Interview cover story in February 2020. “We both partook of Tate. … Who was a very patient human being, given that he dated us both.”
Credit: Robert Isenberg/Anarchy Prods/Kobal/Shutterstock
2 of 9
Troy Aikman
The Proposal actress had a brief romance with the former NFL star in 1995. They were linked again in 2014 after her divorce from James.
Credit: Linda Kaye/AP/Shutterstock; Dave Lewis/Shutterstock
3 of 9
Don Padilla
Bullock revealed in 1996 that she had been dating someone for approximately 10 months, which many believed was the film tech since he attended the July 1995 premiere of The Net with her. “[He's a] really sweet person,” she told Detour of her unidentified boyfriend. “It’s been rough because of all this that happened plus he’s working all the time and I rarely get to see him. But for a year I was by myself trying to date and I’m telling you dating was the worst experience I ever had. I seem to have attracted everyone whose intentions were not the best.”
Credit: Dave Lewis/Shutterstock
4 of 9
Matthew McConaughey
The A Time to Kill costars kept their relationship quiet for two years from 1996 to 1998, when they split. However, they remain pals years later. “It’s the work we both put in. There’s a great amount of respect and love,” she told Cosmopolitan in 2003. “I feel very cared for by Matthew. No matter where he is in his life or where I am in mine — he could be married — I know we would stay close.”
Credit: eter Brooker/Shutterstock
5 of 9
Bob Schneider
Bullock dated the musician from 1999 to 2001. “As celebrities go, Bob and I have a very low-key relationship,” she told Cinema.com in 2000. “It’s something I learned through trial and error.”
Credit: Suzanne Cordeiro/Shutterstock; Andrew Gombert/EPA/Shutterstock
6 of 9
Ryan Gosling
The Murder by Numbers costars were an item from 2002 to 2003. Gosling called Bullock one of the “greatest girlfriends of all time” in a 2011 interview with The Times.
Credit: Bei/Shutterstock
7 of 9
Jesse James
The Bird Box star met the West Coast Choppers founder while touring the set of his show Monster Garage. They tied the knot in July 2005, but he faced allegations of infidelity with multiple women in March 2010. The pair finalized their divorce in June 2010 after he sought treatment at a rehabilitation facility.
“Yeah, I did cheat on my wife, yeah,” James told DailyMail.com in March 2017. “I stood up and took accountability for it and apologized. And that’s [the] end of story.”
Credit: BDG/Shutterstock
8 of 9
Chris Evans
Bullock was linked to the Captain America star in 2014. An insider told Us at the time that Evans was “pursuing Sandra.”
The Two Weeks Notice actress joked about their connection in June 2014. “You guys are a little behind,” she told Entertainment Tonight. “We’ve since married and it started breaking apart, so we separated. We filed for divorce, and I hope everyone can respect our privacy. But we’re going to remain friends and share responsibility of the farm animals we’ve taken on because you just can’t abandon the animals.”
Credit: Jonathan Hordle/Shutterstock; Jim Smeal/BEI/Shutterstock
9 of 9
Bryan Randall
The Virginia native began dating Randall in 2015 after he photographed her son Louis’ birthday party. While the couple largely kept their romance out of the spotlight, a source revealed to Us in September 2018 that they were stronger than ever. “Bryan makes her feel safe and completely takes care of her,” the insider said. “[He’s her] rock.”
In August 2023, a source exclusively told Us that the duo’s relationship was on the rocks after they took some time apart in 2022.
“The feeling is Sandra might be hoping for some type of miracle — that they’ll work things out after this long cooling-off period,” the insider said, adding that the chances of the pair reconciling was “a long shot.”
Days later, Randall’s family announced that the photographer had died at age 57 after a private three-year battle with ALS.
“It is with great sadness that we share that on August 5, Bryan Randall passed away peacefully after a three-year battle with ALS,” the family’s statement to People read. “Bryan chose early to keep his journey with ALS private and those of us who cared for him did our best to honor his request.”
Credit: Snorlax/MEGA
