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

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Her Hollywood career is dotted with acting credits in films like 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 monsters. Just like her illustrious long-running career, Sandra Bullock’s relationship through the years has equally been quite eventful. Let’s delve into the dating history of the Hollywood screen diva; from high-profile relationships, a star-studded array of ex-lovers, headline-grabbing breakups and every other thing in between.

Who Is Sandra Bullock Dating?

Back in 2015, Sandra Bullock got together with former high fashion model and international photographer Bryan Randall. Initially alleged that the duo met through mutual friends, it has been confirmed that they first met when the Oscar winner hired Randall to cover the birthday party of her son Louis. The couple moved in together in early 2016 and have continued to maintain a relatively low profile. Randall has never been married before but he has a grown daughter named Skylar Staten Randall from a past relationship and now a father figure to Bullock’s children Louis and Laila.

Bryan Randall is the founder of Los Angeles-based lifestyle photography company Brian Randall Photography and also runs a professional boutique photo studio located on Mornington Peninsula in Victoria, Australia. In his heydays, Randall also worked as a high-fashion model for menswear fashion brands like Saint Laurent and Hugo Boss. Among his notable magazine features is a spread in the September 2011 issue of Harper’s Bazaar Singapore in which he posed alongside supermodel .

Sandra Bullock’s Relationship Through The Years

Tate Donovan

Sandra Bullock’s first romantic involvement with a fellow celeb dates back to the 1990s when she got together with Hollywood actor and director Tate Donovan. The pair reportedly met in 1990 while filming the romantic comedy Love Potion No. 9. It’s been widely reported that Bullock and Donovan even got engaged at some point, however, this was never truly confirmed. Sandra Bullock’s relationship with Tate eventually came to an end in 1994, leaving the actress highly distraught.

Matthew McConaughey

Shortly after they starred together in the 1996 film A Time to Kill, Sandra Bullock and Hollywood heartthrob  were linked to a romantic relationship. Classic Bullock style, there was no formal confirmation of their romance, however, there was sufficient public appearances and PDA to authenticate the speculations. Sandra Bullock’s relationship with the actor lasted for roughly 2 years as it came to an abrupt end in 1999.

Bob Schneider

At the time she was based in Austin, Texas, Sandra Bullock had a 2-year relationship with Texas-based music artist Bob Schneider whom she met in 1999. The romance proved to be a major career booster for Schneider as some of his songs got featured in a number of Bullock’s films. However, their blissful working relationship couldn’t keep the flame burning for too long as the duo went their separate ways in 2001.

Ryan Gosling

On Sandra Bullock’s star-studded list of ex-lovers is Canadian-born Hollywood actor and musician Ryan Gosling, her co-star in the film Murder by Numbers (2002). Though shortlived, Sandra Bullock’s relationship with the hunk gained a lot of media attention. The romance lasted for about one year as they called it quit in 2003. According to her now-ex-boyfriend, Ryan Gosling, their relationship was overwhelmed by the massive media buzz which it generated.


Marriage to Jesse James

Sandra Bullock’s longest relationship yet is her 5-year marital union with American TV personality Jesse James, best known for his work on the reality series Monster Garage. The two are said to have met when Bullock arranged to meet James with her 10-year old godson as a Christmas gift for the latter. The rest is history as their relationship culminated in their getting married on July 16, 2005.

In early 2010, major trouble brewed in the couple’s paradise as a media scandal arose in which several women alleged to have had affairs with Jesse James. The scandal took a huge toll on Bullock as she canceled a number of public engagements at the time. In a public apology issued on March 18, 2010, James declared that most of the rumours were untrue, however, he did not refute all the claims. He eventually checked into a rehab facility in a bid to salvage their marriage but his efforts were too late as Bullock filed for divorce on April 28, 2010. Their divorce was finalized on June 28, 2010, bringing a rather unfortunate end to their 5-year union.

Troy Aikman

Sandra Bullock’s relationship history also extends beyond Hollywood as the Oscar-winning actress has 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 lowkey romantic involvement with Bullock. Their relationship is reported to have begun in 1995 though there was no official confirmation from either of the two.

It remains unclear when their romance came to an end, however, it is said that distance was a major factor to their break up. Interestingly, nearly 2 decades after their first involvement, the former lovers made headlines again in 2014 as they were said to have reconnected. Just like their first involvement, there was also no confirmation of this second episode.

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