Sandra Bullock has been gracing the silver screen for more than 35 years. As much as she may enjoy promoting her latest production projects and film roles, she prefers to keep her personal life to herself.
After her long-time partner, Bryan Randall, died in 2023, though, people couldn’t help but feel interested in The Proposal actor’s love life. To save you from myriad Google searches, we went ahead and did the sleuthing for you. Ahead, find a full rundown of the 59-year-old actress’s love life.
Sandy B met Tate Donovan on the set of Love Potion No. 9, which began filming in 1990 and premiered in 1992. Back in 1995, Sandra revealed to Vanity Fair that she “chased [Donovan] like a dog.”
The pair dated for a few years before calling it quits in 1994. Although they broke up, Sandra continued to view Tate as the love of her life.
"Everybody has one that is apart from all the rest … He brought out everything in me that was good, that was bad, that was suppressed," she told Barbara Walters in 1996. Then, in 1997, she told Rolling Stone, “You have one great love in life, and I've had it."
The Proposal actress took a break from actors and, in 1995, paired up with one of the most famous football players in the game (at the time), Dallas Cowboys quarterback Troy Aikman. This remains somewhat speculative, though, as Sandy B never actually confirmed their romance, she’s just been historically linked to the former football star and current NFL announcer.
In 1995, Sandra took Don Padilla, a film tech, as her date to The Net premiere. While little is known of their relationship, speculation swirls that he is responsible for helping her get over Tate. In a 1996 interview with Detour, she admitted to seeing someone for 10 months and noted that he was a “really sweet person.” "It's been rough because of all this that happened plus he's working all the time and I rarely get to see him,” she added. “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."
Sandra moved on to dating her A Time to Kill co-star, Matthew McConaughey in 1996, though, in typical Sandy B fashion, she kept it under wraps. Although the pair split in 1998, she continues to hold Matthew in great respect. “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.”
From 1999 to 2001, Sandra dated Austin indie-rocker, Bob Schneider. “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.”
Sandra found herself linked to Ryan Gosling from 2002 to 2003 following their time on set together for 2002’s Murder by Numbers. In an interview with Cosmo, the Gravity actress revealed that Ryan had a way of bringing her back down to earth, noting that he taught her "to chill. I live my life at a manic pace, and he's taught me to disregard all that isn't important. He's like a little Buddha."
Years after their relationship fizzled out, the duo continues to hold each other in high regard. In a 2011 interview with The Times, Ryan called Sandra one of the “greatest girlfriends of all time.”
After dating her way through the ‘90s and early ‘00s, Sandra met West Coast Choppers founder Jesse James and instantly hit it off. They got married in July 2005 and even began the adoption process for her son, Louis, in January 2010. However, following infidelity allegations that year, they divorced in June 2010. He eventually admitted to the allegations, telling Daily Mail in 2017 that, “Yeah, I did cheat on my wife, yeah. I stood up and took accountability for it and apologized. And that’s [the] end of story.”
Although rumors swirled that Sandra and Chris Evans were an item in 2014, Sandy confirmed that they were just friends. Nevertheless, Chris told E! News and Playboy that she was his childhood celebrity crush. “I used to be in love with Sandra Bullock when I was growing up—Sandy B. was my girl,” he told Playboy.
Sandra began dating photographer Bryan Randall after he photographed her son Louis’s birthday party. The pair dated for eight years but never got married. Tragically, Bryan died at the age of 57 in August 2023, following a private 3-year battle with ALS.
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