Sandra Bullock’s Dating History: Photos of the Men She’s Dated

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August 8, 2023 3:01PM EDT
Sandra Bullock Jesse James
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Sandra Bullock is one of Hollywood’s most beloved leading ladies. And while the brunette beauty has been in her fair share of big-screen rom-coms, the star tries to keep her own relationships more private. She’s dated a few dudes, and was even married from 2005 to 2010, but tends to keep tight-lipped about her romances. She dated Bryan Randall from 2015 until 2023, when he tragically died of ALS.

One of Miss Bullock’s earliest public relationships was with co-star Tate Donovan. It turns out fellow star George Clooney was actually the one who set them up too! Ready to learn more about the men who Sandra Bullock has loved? Check out our gallery for her complete relationship history.

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Tate Donovan

Tate Donovan
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Sandra and Tate met in 1990 on the set of ‘Love Potion No. 9’ and were together until 1994. Sandra later confessed to being a bit forward at the start, telling Vanity Fair she ‘chased him like a dog’ in 1995.

July 25, 2022, 5:42PM
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Matthew McConaughey

Matthew McConaughey
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Sandra Bullock and Matthew McConaughey, seen here in 1997, quietly began dating after meeting on ‘A Time to Kill’. They were together for two years and still remain friends.

Sandy opened up about their dynamic with Cosmopolitan in 2003, saying ‘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.’

July 25, 2022, 5:42PM
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Jesse James

Jesse James
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Sandra Bullock married biker Jesse James in 2005, seen here together at the 2010 Screen Actors Guild Awards. The pair met after she stopped by his show ‘Monster Garage’. The marriage was a massive failure, however. The West Coast Choppers founder was caught cheating on Sandra with multiple women, which he later copped to. They divorced in 2010.

July 25, 2022, 5:42PM
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Troy Aikman

Troy Aikman
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Football MVP and sportscaster Troy Aikman was once one of Sandra Bullock’s suitors. The stars dating in 1995 and reunited in 2014 after her divorce from Jesse James.

July 25, 2022, 5:42PM
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Bob Schneider

Bob Schneider
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Musician Bob Schneider was Sandra Bullock’s beau from 1999 to 2001. She called their relationship ‘very low-key’ in a 2000 interview. ‘It’s something I learned through trial and error.’

July 25, 2022, 5:42PM
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Ryan Gosling

Ryan Gosling
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Ryan Gosling and Sandra Bullock, here at thed 2002 Cannes Film Festival, had a brief romance. After working on ‘Murder by Numbers’ together, they dated from 2002 to 2003. Ryan still has fond feelings for his ex, calling her one of ‘greatest girlfriends of all time’ in a 2011 interview with The Times.

July 25, 2022, 5:42PM
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Chris Evans

Chris Evans
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Chris Evans and Sandra Bullock were rumored to be an item around 2014. Nothing was ever confirmed but the star was asked about the romance during a 2014 chat with Entertainment Tonight. Deftly navigating the ask, she joked that the duo had already married and divorced. ‘You guys are a little behind,’ she winked.

July 25, 2022, 5:42PM
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Sandra Bullock & Bryan Randall At ‘Ocean’s 8’ Premiere

Sandra Bullock & Bryan Randall At ‘Ocean’s 8’ Premiere
Richard Young/Shutterstock

Sandra Bullock started dating Bryan Randall in 2015. The two kept their relationship extremely private and mostly out of the public eye. In Aug. 2023, it was confirmed that Bryan had passed away after secretly battling ALS for three years.

August 8, 2023, 7:43AM