Sandra Bullock’s Dating History: Jesse James, Bryan Randall and More

Credit: BDG/Shutterstock; Snorlax/MEGA; Bei/Shutterstock

Sandra Bullock’s Dating History: Jesse James, Bryan Randall and More

Leading lady on and off the screen! Sandra Bullock slays the love game in real life just as epically as she does in her charming romantic movies. The actress opened up about searching for the L-word in 1999. “Maybe people spend too much time looking,” she told Entertainment Tonight. “I think we spend too much time looking for things that are more things that society wants us to look for and that we get from a magazine rather than that are really worth it.” Bullock then elaborated on the qualities she wanted in a partner. “Who cares how much somebody makes for a living? In the end, we’re all going to be old and wrinkled,” she explained. “You’d like to know that that person can make you laugh and think, you know, can really stimulate you and excite you when they’re gone and you think about them. Somebody you can admire and be proud of and sit back and go, ‘This is my man.’ And whether or not he’s a millionaire or he’s a painter, a musician or somebody who just, you know, shucks clams, it’s that respect level that we forget to look for.” The Oscar winner seemed to find her match in Jesse James, whom she wed in July 2005. However, they divorced in June 2010, three months after his cheating scandal. [jwplayer AUq40yX3-l3ahXupL] “We’re all where we’re supposed to be,” she told Vogue in October 2013. “I am exactly where I want to be now. You can’t go backward. I’m not going backward. I’m grateful that I’m here, blessed to have what I have. Nobody can be prepared for anything.” Bullock announced the adoptions of son Louis in April 2010 and daughter Laila in December 2015. After becoming a mother, the Oscar winner moved on with Bryan Randall in 2015. “Bryan is such a sweet soul, and things couldn’t be more different from the toxic relationships she’s been in before,” a friend of Bullock exclusively told Us Weekly in June 2019, adding that she “knows Bryan is The One.” Despite their long-term commitment, the pair are waiting to make things official. “They’re totally open to getting married down the line but there’s no pressure on either side,” an insider told Us in November 2020. “[It’s] more of an acknowledgment that they’re lucky to have each other and that it doesn’t take a piece of paper or formality to ensure happiness.” Scroll down to revisit Bullock’s complete dating history, from marriage to long-term love and more.

Credit: Robert Isenberg/Anarchy Prods/Kobal/Shutterstock

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: Linda Kaye/AP/Shutterstock; Dave Lewis/Shutterstock

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: Dave Lewis/Shutterstock

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: eter Brooker/Shutterstock

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: Suzanne Cordeiro/Shutterstock; Andrew Gombert/EPA/Shutterstock

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: Bei/Shutterstock

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: BDG/Shutterstock

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: Jonathan Hordle/Shutterstock; Jim Smeal/BEI/Shutterstock

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: Snorlax/MEGA

Bryan Randall

The Virginia native began dating Randall in 2015 after he photographed her son Louis’ birthday party. While the couple have stayed 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.”

The duo consistently spark wedding rumors, but her rep told Us in March 2018 that Bullock and Randall “are not married.”