Sandra Bullock Is “Open to the Possibility” of Dating—Here’s Her Complete Relationship History
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Sandra Bullock is reportedly open to dating again after the passing of her long-term partner Bryan Randall in 2023. While Bryan was Sandra’s longest and most significant relationship, we’re taking a look back on her dating history–including with celebs like Tate Donovan and Ryan Gosling (IKR, who knew?).
Tate Donovan: 1990 to 1994...ish?
Tate (or as I call him, Jimmy Cooper from The O.C.) and Sandra met while filming Love Potion #9, and even got engaged before they eventually split.
“I adored Tate so much,” Sandra told Vanity Fair about a year after they parted ways. “It’s like they say, there’s one person in your life, and Tate and I are closer than any two people I’ve ever experienced in my life. There’s nobody that means more to me, and I know for a fact that I mean the most to him in that certain way.”
ALSO, can we all watch this movie together?
Troy Aikman: Circa 1995
Sandra and Troy (who played for the Dallas Cowboys) were so low-key, we wouldn’t even know they’d dated if it weren’t for—unsubstantiated!—tabloid rumors that they had a reunion in 2015.
Matthew McConaughey: 1996 to 1998
These two starred in A Time to Kill together and apparently sparks flew! They actually stayed friends post-breakup, and Sandra told Cosmopolitan in 2003 (*waves hi*), “It’s the work we both put in. There’s a great amount of respect and love. 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.”
Bob Schneider: 1999 to 2001
It was short. It was sweet. And it was very chill. As Sandra told Cinema.com in 2000, “As celebrities go, Bob and I have a very low-key relationship. It’s something I learned through trial and error.”
Ryan Gosling: 2002 to 2003
Surprise! Sandra and Ryan dated thanks to filming Murder by Numbers, and she even joked to Cosmo about the relationship while it was happening: “Let me see if I can answer that politically and correctly. We’re friends...If you were to add the word just, it would probably be a bit of a lie. So I’d say we’re friends.”
Jesse James: 2003 to 2010
Sandra and Jesse met when he was filming Monster Garage, and they got married in 2005. Annnnnd then they split after multiple women came forward and claimed they’d had affairs with Jesse. He later said in an interview with the Daily Mail, “Yeah, I did cheat on my wife, yeah. I stood up and took accountability for it and apologized. And that’s end of story.”
Chris Evans (Maybe): 2014
This one is just a rumor, but E! News DID report that “They are not in a relationship, but they are definitely hanging out and are in the early getting-to-know-each-other phase. They haven’t put a title on it, but they really like each other.”
Bryan Randall: 2015 to 2023
Sandra met Bryan in 2015 and their relationship was pretty private. But Sandra opened up about Bryan a few times—including in 2021 when she told Red Table Talk, “He’s the example that I would want my children to have. I have a partner who’s very Christian and there are two different ways of looking at things. I don’t always agree with him, and he doesn’t always agree with me. But he is an example even when I don’t agree with him.…We’re saying it differently but we mean the exact same thing.”
Bryan sadly died in 2023 after a private battle with ALS. This past summer, a source told People that Sandra’s friends “gave her the support that she needed both during his illness and afterward. She is grateful for all the love. Everyone helped to lift her up after Bryan passed.”
Where Things Stand Now
Following the tragic death of her partner, a source told Us Weekly that Sandra is “open to the possibility” of dating in the future, but for now, she’s “healing slowly, keeping Bryan’s memory alive and focusing on her children.”
An insider also told In Touch, “She knows Bryan wanted her to pick up the pieces and try to find a good guy.”
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