Sandra Bullock's Complete Relationship History

Sandra Bullock has been an icon of American cinema since she burst onto the scene in the '90s. With credits in dozens of beloved films that include "Speed," "Miss Congeniality," "Two Weeks Notice," "The Proposal," "The Blind Side," and "The Lost City," Bullock has been a rom-com heroine and an action star — sometimes both at the same time.

While Bullock may be best known for her on-screen romances, her off-screen love life has been equally dramatic. Over the years, she's been linked to sports star Troy Aikman, actors Ryan Gosling and Matthew McConaughey, and most recently, photographer Bryan Randall. Bullock has only married once — to West Coast Choppers CEO Jesse James – but it was Randall whom Bullock considered the "love of [her] life." In late 2021, Bullock explained on "Red Table Talk," saying, "I don't wanna say do it like I do it, but I don't need a paper to be a devoted partner."

Before finding her prince, though, the actor had to kiss a few frogs.

Sandra Bullock's first boyfriend was a childhood sweetheart. The soon-to-be star dated Greg Davis while attending high school in Virginia. Not much is known about Davis or his relationship with Bullock; however, it does seem they were pretty close. In fact, Bullock and Davis were even named "Most Likely Couple to Get Married" in school, according to Rolling Stone. Clearly, though, that didn't happen!

Although Bullock and Davis' relationship didn't last, they both ended up pursuing careers in Hollywood. While Bullock went on to star in films like "Gravity," "Ocean's Eight," and "Bullet Train," Davis worked behind the scenes, often as a rigging gaffer in the camera and electrical department, on the sets of popular films like "The Hunger Games: Catching Fire," "Passengers," and "The Tomorrow War."

It seems that, at least for a time, Davis regretted no longer being in a relationship with the actor. In 1995, he penned an essay titled, "I was the pillock who lost Sandra Bullock," which was published in Sunday Magazine.

Early in her acting career, Sandra Bullock went on to date Tate Donovan. Bullock and Donovan met in 1991 when they both starred in "Love Potion No. 9." As Bullock told Vanity Fair in 1995, she "chased him like a dog." She went on, saying, "I adored Tate so much. It's like they say, there's one person in your life, and Tate and I are closer than any two people I've ever experienced in my life." In fact, Bullock thought that they still meant a lot to each other at the time, even though they'd since broken up. "I can't explain why things worked out the way they did," she said. "We both know why it happened." 

You may remember Donovan as Joshua, the short-lived boyfriend of Rachel in "Friends." As it turns out, Jennifer Aniston also dated the actor. Years later, during a conversation with Aniston for Interview magazine, Bullock said, "We both partook of Tate ... who was a very patient human being, given that he dated us both." Aniston replied, "He seems to have a type." Bullock came back, "Talented. Funny. Kind. Introspective. Generous." At least Bullock was left with a friend in Aniston despite her relationship with Donovan failing to work out.

When Troy Aikman began dating Sandra Bullock, he was the star quarterback for the Dallas Cowboys. The pair dated in the mid-1990s before eventually ending things when the long-distance relationship reportedly became too difficult.

Years later, rumors began to spread that the pair were picking up where they'd left off. "Sandra and Troy have always got on well, but she doesn't want to publicly date him until she's 100 per cent ready for a relationship," a source told Closer in 2014. "She's also worried about getting her heart broken, so a no-strings fling is fine, but she's not committing to anything yet." By then, Aikman had retired from football and was working as an NFL color commentator for Fox. Bullock's career was still going strong and she'd since been married and divorced and welcomed a son. "Sandra hasn't introduced Troy to Louis as anything other than mommy's friend," the source said.

In the mid-'90s, Sandra Bullock was briefly linked to Don Padilla, who worked in the camera department as a grip at the time. Padilla accompanied Bullock to the premiere of "The Net" in July 1995. In November of that year, couple also attended a book launch together.

Without naming Padilla, Bullock referred to him as someone she'd been seeing for 10 months when interviewed by Detour in 1996. "Really sweet person," she said. "It's been rough because of all this that happened plus he's working all the time and I rarely get to see him. But for a year I was by myself trying to date and I'm telling you dating was the worst experience I ever had." Bullock went on to say, "I seem to have attracted everyone whose intentions were not the best." Could she have been referencing Troy Aikman? We may never know for certain.

Following her relationship with Don Padilla, Sandra Bullock found love again — this time with actor Matthew McConaughey, whom she met while they were both filming "A Time to Kill" in 1996. The pair dated for about two years.

As Bullock told Cosmopolitan in 2003, though, she and McConaughey remained friends. "It's the work we both put in," she explained. "There's a great amount of respect and love. I feel very cared for by Matthew." After breaking up, McConaughey admitted,"I do love her, and will always love her. Absolutely." He also revealed he was holding out hope that they could date again. While that didn't happen, they did remain freinds — as Bullock knew they would. "No matter where he is in his life or where I am in mine — he could be married — I know we would stay close," she told Cosmo.

In 2014, McConaughey referenced Bullock in a speech after she won the Decade of Hotness award at the Guys Choice Awards. "I've worked with you. I've tried to kiss you — successfully and unsuccessfully," he said as the audience laughed. He continued, saying, "Here is to your decade of hotness. I'm glad to say that I knew you the decade before." Bullock then got onto the stage and gave him a hug — how cute!

Sandra Bullock dated musician Bob Schneider from 1999 to 2001. During their relationship, the two were involved in a plane crash after leaving the premiere of "Miss Congeniality." Thankfully, both Schneider and Bullock were uninjured in the crash.

As Bullock revealed in an early 2000s interview with Cinema.com, "As celebrities go, Bob and I have a very low-key relationship. We live our life together one day at a time. It's something I learned through trial and error." The actor revealed that she struggled with saying "I love you" at the time. "But then Bob and I talk German all the time to each other [they both grew up in Germany], which is terribly funny because I'm so bad at it," she went on. "Maybe saying 'I love you' in German could be easier for me."

While Bullock wanted to keep her relationship under the radar, she did try to help Schneider get into the public eye as an artist. "Sandra discovered Bob and has really promoted him. He is very talented," the actor's friend, Rosanna Arquette, said. In fact, Schneider's song "Bullets" made it onto the soundtrack for "Miss Congeniality." 

In 2003, rumors began to spread that Sandra Bullock was dating cyclist Lance Armstrong. The pair were linked just one month after his split from his wife, Kristin Richard. "She is absolutely smitten," an anonymous source alleged to SF Gate. "She really believes Lance could be the one. He's successful, determined, a survivor and, let's not forget, gorgeous."

The rumor came at a time when Bullock was still thought to be dating Matthew McConaughey. "Up to now, Sandra has always gone back to Matthew, but Lance has changed all that," the source said. Apparently, Bullock and Armstrong were even seen on a date in New York. "They were all over each other," a witness claimed. "She was rubbing his thigh and he was massaging her shoulders. At one point they even started feeding each other."

Later that year, Bullock and Armstrong were photographed together at a party celebrating the launch of his book, "Every Second Counts." It is not known when Armstrong and Bullock broke up, but it seems their relationship was pretty short-lived. 

One of Sandra Bullock's most publicized relationships was with actor Ryan Gosling, whom she met on the set of "Murder by Numbers." The pair had a significant age gap — Bullock was 38, while Gosling was only 21 at the time. However, they soon began making public appearances together. Their first appearance as a couple was in 2002 at the "Murder by Numbers" premiere.

The following year, Bullock seemed to concede that the two were in some form of relationship. When asked by Cosmopolitan if they were friends, Bullock explained, "Let me see if I can answer that politically and correctly. We're friends," she said. However, they weren't just friends. "If you were to add the word just, it would probably be a bit of a lie. So I'd say were friends," Bullock admitted. As the "Miss Congeniality" star went on to explain, she learned a lot from Gosling despite their age difference. "I live my life at a manic pace, and he's taught me to disregard all that isn't important. He's like a little Buddha."

However, later that year, the pair broke up. Nevertheless, Gosling always remembered Bullock fondly. "I had two of the greatest girlfriends of all time," he told the Independent in 2011, speaking of Bullock and Rachel McAdams, whom he later dated. "I haven't met anybody who could top them."

In 2003, Sandra Bullock met Jesse James, best known as host of the reality show "Monster Garage" and founder of West Coast Choppers. Bullock had taken her godson on a trip to visit the West Coast Choppers motorcycle garage. Apparently, her godson was too starstruck to talk. "I thought, God, do I have to make conversation?" Bullock recalled to Vanity Fair of their first meeting. James began sending her emails (when she refused to give him her number). "So basically through a courtship of letters, which I didn't even recognize, I learned about a human being," she said. "It was not something I wanted, needed, or looked for, but because he was a stronger person than I was, spiritually and on a tolerance level, I was lucky enough that he educated me."

By 2005, the pair had tied the knot. At first, Bullock couldn't have been happier. "People say, 'Oh, my God, you're going to have sex with one person the rest of your life.' I hope I have sex with him for the rest of my life, because I like it!" she said.

However, by March 2010, their marriage was on the rocks after James reportedly cheated on Bullock with a number of women. "There is only one person to blame for this whole situation, and that is me," James said in a statement to People. The couple was in the middle of adopting a child at the time. In April, Bullock filed for divorce and went on to adopt her son as a single parent.

In 2014, Sandra Bullock was rumored to be dating Captain America himself, Chris Evans. Evans had previously admitted she was his celebrity crush. "I used to be in love with Sandra Bullock when I was growing up," he told Playboy in 2012. "Sandy B. was my girl. I remember seeing 'Speed' when I was in seventh grade and just thinking, That's her. I can't say I know her, but from what I've heard, she's fantastic." 

The pair appeared to get close in 2014 and they were even spotted on a date in Hollywood, but sources were adamant that any romance between them was still in the very early stages. "They are not in a relationship, but they are definitely hanging out and are in the early getting-to-know-each-other phase," a source told E! News. "They haven't put a title on it, but they really like each other." Later that year, however, Bullock confirmed that the short-lived relationship had run its course.

Just one month after the rumors began to spread, she joked to Entertainment Tonight, "You guys are a little behind. We've since married and it started breaking apart, so we separated. We filed for divorce, and I hope everyone can respect our privacy. But we're going to remain friends and share responsibility of the farm animals we've taken on, because you just can't abandon the animals." Clearly, any romance between them wasn't very serious.

One of Sandra Bullock's most significant relationships came in the form of Bryan Randall, a photographer. The pair were together from 2015 until his death in August 2023. "It is with great sadness that we share that on Aug 5, Bryan Randall passed away peacefully after a three-year battle with ALS," his family said in a statement to People. "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."

For Bullock, Randall was, as she said during an appearance on "Red Table Talk," the "love of [her] life." She continued, saying, "We share two beautiful children — three children, his older daughter. It's the best thing ever." Nevertheless, she didn't feel the need to walk down the aisle again.

As Bullock's sister wrote in an Instagram tribute, Bullock was with Randall as a carer and partner up until his death. "ALS is a cruel disease but there is some comfort in knowing he had the best of caretakers in my amazing sister and the band of nurses she assembled who helped her look after him in their home," she wrote on Instagram.

Throughout Sandra Bullock's life, there have been plenty of relationships along with a couple almost-boyfriends. One man she never dated (but definitely wanted to) was Keanu Reeves, her co-star in "Speed." Although the pair were never more than friends, they both admitted to crushing on each other. 

"I think about how sweet Keanu Reeves was and how handsome he was," she explained on "The Ellen DeGeneres Show." "It was hard, it was really  — it was hard for me to, like, really be serious. Like, he would look at me, and I'd be like [giggling]," she said. She added, "Never dated him. There was just something about me that I guess he didn't like." However, Reeves later confirmed that wasn't exactly true. When Reeves later appeared on "The Ellen DeGeneres Show," she asked him about Bullock's comments. "She obviously didn't know I had a crush on her either, so," he admitted.

It is possible that George Clooney and Sandra Bullock could've also gone the distance if they ever started dating. However, Clooney has always maintained that their relationship is strictly platonic. "She was dating one of my best friends," Clooney said to E! News, referring to an unnamed partner. "There's a certain bro code, you know what I mean?" he added. "I've known her a long, long time." Bullock admitted to Access that Clooney was instead a wingman. "George went to [his friend] and said, 'If you don't marry her, I will,'" she recalled.