Sandra Bullock’s Relationships Through The Years, Who Is She Dating Now?
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Her Hollywood career is peppered with acting credits in films such as Speed (1994), The Net (1995), Miss Congeniality (2000), The Proposal (2009), The Blind Side (2009), Gravity (2013), Minions (2015) and Ocean’s 8 (2018), all of which were box office hits. Just like her illustrious long career, Sandra Bullock’s relationships have been quite eventful over the years. Let’s dive into the dating history of the Hollywood screen diva; high-profile relationships, a star-studded cast of ex-lovers, headline-grabbing breakups, and everything in between.

Sandra Bullock’s Relationships Through The Years, Who Is She Dating Now?
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Who Is Sandra Bullock Dating?

In 2015 Sandra Bullock met with former high fashion model and international photographer Bryan Randall. Originally it was claimed that the duo met through mutual friends, but it was confirmed that they first met when Oscar-winning actress Randall asked her to cover her son Louis’ birthday party. The couple moved in together in early 2016 and have continued to keep a relatively low profile. Randall has never been married before, but he has an adult daughter named Skylar Staten Randall from a previous relationship and is now a father figure to Bullock’s children Louis and Laila.

Sandra Bullock’s Relationships Through The Years, Who Is She Dating Now?
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Bryan Randall is the founder of the Los Angeles-based lifestyle photography company Brian Randall Photography and also runs a professional boutique photography studio on the Mornington Peninsula in Victoria, Australia. In his heyday, Randall also worked as a high-fashion model for men’s fashion brands such as Saint Laurent and Hugo Boss. His notable magazine contributions include a feature in the September 2011 issue of Harper’s Bazaar Singapore, where he posed alongside supermodel Cindy Crawford.

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Sandra Bullock’s Relationship Through The Years

Tate Donovan

Sandra Bullock’s Relationships Through The Years, Who Is She Dating Now?
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Sandra Bullock’s first romantic relationship with a celebrity colleague dates back to the 1990s when she met Hollywood actor and director Tate Donovan. According to reports, the two met in 1990 during the shooting of the romantic comedy Love Potion No. 9. It was widely reported that Bullock and Donovan even got engaged at some point, but this was never really confirmed. Sandra Bullock’s relationship with Tate finally ended in 1994, leaving the actress very desperate.

Matthew McConaughey

Sandra Bullock’s Relationships Through The Years, Who Is She Dating Now?
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Shortly after they played together in the 1996 film A Time to Kill, Sandra Bullock and Hollywood heart-throb Matthew McConaughey were associated with a romantic relationship. In the classic Bullock style, there was no formal confirmation of their romance, but there were enough public appearances and PDAs to confirm the speculation. Sandra Bullock’s relationship with the actor lasted for about 2 years when it came to an abrupt end in 1999.

Bob Schneider

Sandra Bullock’s Relationships Through The Years, Who Is She Dating Now?
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At the time she was based in Austin, Texas, Sandra Bullock had a two-year relationship with Texas-based music artist Bob Schneider, whom she met in 1999. The romance proved to be an important career boost for Schneider, as some of his songs appeared in a number of Bullock’s films. However, their blissful working relationship could not keep the flame burning for too long when the duo went their separate ways in 2001.

Ryan Gosling

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Sandra Bullock’s relationships star-studded list of ex-lovers includes Canadian-born Hollywood actor and musician Ryan Gosling, her co-star in the film Murder by Numbers (2002). Although it was short-lived, Sandra Bullock’s relationship with the Brocken attracted a great deal of media attention. The romance lasted for about a year when it ended in 2003. According to her now ex-boyfriend Ryan Gosling, her relationship was overwhelmed by the massive media frenzy it caused.

Marriage with Jesse James

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Sandra Bullock’s longest relationship to date is her 5-year marriage to American TV star Jesse James, who is best known for his work on the reality series Monster Garage. The two are said to have met when Bullock arranged a meeting with their 10-year-old godson as a Christmas present for James. The rest is history, as their relationship culminated in their marriage on July 16, 2005.

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In early 2010, big trouble was brewing in the couple’s paradise when a media scandal broke out in which several women claimed to have had affairs with Jesse James. The scandal took an enormous toll on Bullock, as she canceled a number of public engagements at the time. In a public apology released on March 18, 2010, James stated that most of the rumors were untrue, but he did not refute all the allegations. He eventually went to a rehab facility to save her marriage, but his efforts came too late when Bullock filed for divorce on April 28, 2010. Their divorce was finalized on June 28, 2010, which was a rather unfortunate end to their 5-year marriage.

Troy Aikman

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Sandra Bullock’s relationships history also extends beyond Hollywood, as the Oscar-winning actress also dated retired American football quarterback Troy Aikman, known for his 12-season stint with the Dallas Cowboys. In his heyday as an NFL star, Troy had a relatively minor romantic relationship with Bullock. Their relationship is said to have begun in 1995, although there has been no official confirmation of either of them.

It remains unclear when their romance ended, but it is said that distance was an important factor in their separation. Interestingly, almost two decades after their first relationship, the former lovers hit the headlines again in 2014, when they supposedly found each other again. Just like their first encounter, there was no confirmation for this second episode.