Sandra Bullock’s Dating History, From Keanu Reeves To The Late Bryan Randall

The woman once dubbed ‘America’s Sweetheart’ has had a few of her own. Here is a closer look at Sandra’s dating history amid her late boyfriend’s passing.

• Sandra Bullock is an actress known for her hit movies including Miss Congeniality, Bird Box, Ocean’s 8, and more.
• Her last boyfriend was the late Bryan Randall.
• She was once rumored to be dating Keanu Reeves, however, it was merely a crush.
• Sadly, Bryan died on Aug. 5, 2023, the family confirmed two days later.

“I’ve learned more in the past two years about the word – you know, people say the word ‘love’ and what that means to love somebody,” Sandra Bullock said in a 2013 interview with Entertainment Tonight. “Maybe people spend too much time looking. I think we spend too much time looking for things that are more things that society wants us to look for and that we get from a magazine rather than that are really worth it.”

Apparently, when you stop looking, that’s when you find what you’ve been searching for all this time. Since 2015, Sandra and her late boyfriend Bryan Randall enjoyed a low-key romance, up until his sudden passing in Aug. 2023. His family confirmed the somber news in a statement to HollywoodLife. “It is with great sadness that we share that on August 5th Bryan Randall passed away peacefully after a 3 year battle with ALS. Bryan chose early to keep his journey with ALS private and those of us who cared for him did our best to honor his request,” the statement read.

“We are immensely grateful to the tireless doctors who navigated the landscape of this illness with us and to the astounding nurses who became our roommates, often sacrificing their own families to be with ours,” they added. “At this time we ask for privacy to grieve and to come to terms with the impossibility of saying goodbye to Bryan.” Amid his passing, below is a closer look at Sandra’s dating history – including romances with Ryan Gosling, Matthew McConaughey, and Jesse James.

Sandra Bullock & Bryan Randall

Bryan Randall was a professional photographer and former model. Bryan – who died at 57 years old – ran a photography company called Bryan Randall Photography. He also used to work as a model, posing for Harper’s Bazaar, Hugo Boss, Saint Laurent, and Vogue Paris in the 1990s. He also appeared in a 2011 issue of Harper’s Bazaar Singapore alongside Cindy Crawford.

Like Sandra, 59, Bryan was a parent. He has an adult daughter, Skylar, from a previous relationship. Sandra has two adopted kids: son Louis (b. 2010) and daughter Laila (b. 2012). Bryan has taken on the role of “raising the two kids with Sandra,” according to Us Weekly, who also reports that he’s talking about wanting more children.

Bryan once dated Paris St. John, daughter of The Young and the Restless’ Kristoff St. John and boxer Mia St. John. Mia told Us Weekly in 2015 that Bryan was a “free spirit” who “couldn’t care less about money” and that he’s “kooky, goofy…so funny and very young at heart.”

As for date night, Sandra and Bryan often kept it low-key, according to Us Weekly. While the couple previously enjoyed an occasional night out in Los Angeles, hitting up Craig’s or somewhere fancy, supposedly their ideal date night was often “to send the kids upstairs and snuggle up on a couch with a pizza or a bowl of popcorn.”

How Did Sandra Bullock & Bryan Randall Meet?

Sandra and Bryan first met in 2015, after he was hired to photograph her son Louis’ birthday part, per Us Weekly. The couple kept their romance out of the spotlight for a few years before rumors of a possible marriage began popping up.

“For a year, I was by myself trying to date, and I’m telling you dating was the worst experience I ever had. I seem to have attracted everyone whose intentions were not the best,” Sandra said in a 1996 interview with Detour (h/t E! News). “They were nice people, but they just weren’t suited for me, and that’s hard because I seriously thought I’m never ever going to find anybody that will love me and just enjoy life.”

Most recently, in Nov. 2021, Sandra opened up to Red Table Talk about her thoughts on marriage. “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,” she gushed at the time. “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.”

Sandra Bullock’s Past Relationships

“If you’ve never been around somebody that gives you that feeling of ‘Maybe this could be the one’ or enlivens you that way, I think you get a little scared. I don’t think [my character’s] ever…been across someone that she respected and admired enough to say, ‘You are worth battling it out with for a lifetime,’’ Sandra said in that 2013 interview with ET. “You’d like to know that that person could…make you laugh and think, can really stimulate you and excite you when you’re gone…somebody you can admire and be proud of and sit back and go, ‘This is my man.’ “

“Whether or not he’s a millionaire or if he’s a painter, a musician, or somebody who just shucks clams, I think it’s that respect level that we forget to look for,” she added. Sandra’s romantic history is full of artists, sports, and millionaires.

She first began dating Tate Donovan while filming 1992’s Love Potion No. 9. Sandra and the O.C. alum stayed together for three years and were even engaged before calling it quits. In 1995, she had a brief romance with NFL star Troy Aikman. The following year, she revealed she was dating film tech, Don Padilla.

“[He’s a] really sweet person,” she told Detour of her then-unidentified boyfriend. “It’s been rough because of all this that happened, plus he’s working all the time, and I rarely get to see him.” They were together for about ten months, and she told Rolling Stone in 1997 that the breakdown of her relationship with Padilla affected her work on A Time To Kill.

“I had to look at myself and go, ‘I’m responsible for so many things now, what am I choosing to hold close to my heart? And what do I choose to let go of and not control?’ You learn what you’re made of,” she said. “I could have thrown in the towel, or I could just put my head down and say, ‘OK, give me a windbreaker, I’m going in.’ And it was beautiful to realize that your friends are not just hanging in for the good times. ‘Cause the good times mean absolutely nothing at all.”

Sandra worked opposite Matthew McConaughey on A Time To Kill. The two were rumored to be a couple at the time, and she didn’t correct Cosmopolitan in 2003 when they referred to her as her ex. “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.”

Sandra also dated musician Bob Schneider, former lead singer of Ugly Americans, from 1999 to 2001. From 2002 to 2003, she and Ryan Gosling were an item. After Sandra and Ryan split, she met motorcycle mechanic/entrepreneur/reality television star, Jesse James. The couple first crossed paths while she took her nephew on a tour of his Long Beach shop, per E! News, leading to a romance that ultimately saw them tie the knot in July 2005. The couple split in 2010 after he cheated on her. Afterward, there were rumored romances with Ryan Reynolds and Chris Evans, but that was all speculation and celebrity crushin’.

Sandra was rumored to have dated Keanu Reeves in prior years, however, she set the record straight on that during a 2018 appearance on The Ellen DeGeneres Show. “Never dated him,” Sandra said at the time. “There’s just something about me that I guess he didn’t like.”