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Sandra Bullock dating and marriage history: Ryan Gosling, Jesse James, Bryan Randall, and more

A glimpse into Bullock's past.

Sandra Bullock and Bryan Randall
Photo by BERETTA/SIMS/SHUTTERSTOCK

One can very well imagine how it feels to lose the love of one‘s life. That’s exactly what actress Sandra Bullock is going through now after losing her long-term partner, Bryan Randall on Saturday. A source closer to the family confirmed the news on Monday that Randall died of amyotrophic lateral sclerosis (ALS), a nervous disorder with which he was battling for nearly three years.

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While condolences are pouring in from friends, family, and fans, many people have used this occasion to revisit Bullock’s relationship with Randall, with whom she had a relationship of over eight years. The tragic event has also led fans to recall the actress’s past relationships and romances that always attracted a huge chunk of public and media attention.

Here’s all we need to know about the Gravity star and some of the well-known people she was romantically involved with.

Ryan Gosling

Photo by Denis Makarenko/Shutterstock

Despite the huge age gap, Ryan Gosling, 21, and Bullock, 37 are believed to have immediately hit it off after meeting on the set of the 2002 psychological thriller, Murder by Numbers. Their relationship lasted from 2001 to 2003, during which the pair were spotted making numerous public appearances together which also included their movie’s red carpet appearance in 2002 at Cannes.

The reason for their breakup is still unknown but Gosling blamed the industry for the end of their relationship, saying, “Showbusiness is the bad guy. When both people are in show business it’s too much showbusiness. It takes all of the light, so nothing else can grow.” Years later, Gosling still had good things to say about Sandra and in a 2011 interview, he regarded her as “one of the greatest girlfriends of all time.”

Jesse James

Photo by Billy Farrell/Patrick McMullan/Getty Images

Bullock tied the knot with reality star Jesse James in 2005 after two years of dating. Unfortunately, in 2010 Bullock decided to end things and filed for a divorce. The reason was James’ infidelity as he was later called out for cheating on The Blind Side star with multiple women.

The same year, the couple began their adoption process for their son Louis. Following their split, Bullock became a single parent and in an interview with CBS expressed concern about how the divorce might impact her son, stating,

“I mean, so much had happened. How do you process grief and not hurt your child in the process? It’s a newborn. They take on everything that you’re feeling. So my obligation was to him and not tainting the first year of his life with my grief.”

Following her separation with James, she adopted her daughter Laila in 2015 and began dating Bryan Randall.

Bryan Randall

Photo by Jackson Lee/GC Images

The Proposal star’s long-term relationship was with Bryan Randall who she met on her son’s birthday in January 2015. They started dating a few months later and in August 2015 were seen attending the wedding of Justin Theroux and Jennifer Aniston.

A month later, they were spotted on a double date with the newlywed couple. Later, the couple was spotted going on a couple of dates. In 2021, Bullock spoke in detail about her relationship with Randall on Red Table Talk calling him the “love of her life” as well as clarifying her intention to never marry,

“I am someone who went through the divorce process. I found the love of my life. We share two beautiful children — three children, his older daughter. It’s the best thing ever. I don’t wanna say do it like I do it, but I don’t need a paper to be a devoted partner and devoted mother.”

In 2022, Bullock talked to People about taking time off from work and spending more time with family. “I’m not retiring, just going to not spend time in front of the camera for a while. I have beautiful babies. I’d rather look at them,” is what she stated about her decision to prioritize her family.

Their relationship lasted until Randall’s death on Aug. 5, 2023.

Bullock was also linked with some of the industry’s well-known names like Matthew McConaughey, whom she dated from 1996 to 1998. The pair kept their relationship private and amicably parted ways later. Others include Bob Scheider – with whom she was romantically involved from 1999 to 2001, as well as Captain America star Chris Evans – with whom she was linked in 2014.

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