Unlucky In Love! Inside Sandra Bullock's Past Failed Relationships As Actress Gets 'Cold Feet' About Marrying Bryan Randall

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Source: MEGA

Apr. 18 2022, Published 1:41 p.m. ET

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Sandra Bullock has dated her fair share of Hollywood suitors before getting together with her current boyfriend, Bryan Randall.

While the Miss Congeniality actress, 57, is still on cloud nine with her boyfriend of six years, she's apparently in no rush to get wrapped up in another marriage just yet, considering that her first one went down in flames.

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Even before divorcing ex-husband Jesse James in 2010, the brunette babe hasn't been lucky in love, as she has dated a slew of famous men who just weren't the right fit.


Scroll through the images below to see some of the Hollywood celebrities Sandra Bullock has dated:

Tate Donovan

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Decades before her latest flame, Bullock linked up with Tate Donovan while filming the 1992 film Love Potion No. 9. They ended up dating for three years and were even engaged before calling things off in 1994.

She would later bond with Jennifer Aniston over Tate, who also previously dated the Friends actress.

“We were introduced by our former boyfriend. I say ‘our’ because you and I both partook of this one human being,” Bullock previously told Aniston of their shared past beau, per Us Weekly.

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Matthew McConaughey

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Source: MEGA

Bullock also struck up a romance with heartthrob actor Matthew McConaughey, whom she dated from 1996 to 1998.

Despite going their separate ways, the former flames have since remained on good terms, with Bullock telling 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."

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Bob Schneider

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Source: @bob_schneider_music/Instagram;MEGA
Sandra Bullock

For one of her less publicized relationships, Bullock dated musician Bob Schneider starting in 1999.

Not much is known about their relationship, as Bullock previously stated she wanted to keep things "very lowkey" after learning her lesson from her previous high-profile romances, per Cinema.

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Ryan Gosling

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Bullock also briefly dated Ryan Gosling from 2002 to 2003, previously gushing to Cosmopolitan that The Notebook actor helped her "chill" out. "I live my life at a manic pace, and he's taught me to disregard all that isn't important," she said at the time. "He's like a little Buddha."


Gosling, 41, has also called The Blind Side actress one of the "greatest girlfriends of all time," per Us Weekly.

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Jesse James

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Source: MEGA

Bullock's marriage to James started to breakdown in 2010, just five years after the former spouses' nuptials. Following allegations of infidelity with multiple women, James ended up getting treatment for sex addiction at a rehab facility before they finalized their divorce.

James later owned up to the rumors in a 2017 statement, confessing: "Yeah I did cheat on my wife, yeah," per Page Six. "I stood up and took accountability for it and apologized. And that's [the] end of story."

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Bryan Randall

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Source: MEGA

Randall, 56, is Bullock's current boyfriend, who works as a photographer in Los Angeles, Calif.

The A-lister openly talks about getting married to Randall, although it seems she gets a bit squirmy when it comes time to actually hash out the details. "Whenever the conversation gets serious and turns to setting a date or making any solid plans, she gets cold feet," an insider previously spilled to OK!. “For years, Bryan hasn’t wanted to push too hard because he knows her last marriage ended so badly.”

Only time will tell if Bullock will take the leap of faith and walk down the aisle again.


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