Sandra Bullock Revealed What She Learned from Ryan Gosling When They Dated 20 Years Ago

Sandra Bullock has been gracing the silver screen for more than 35 years. As much as she may enjoy promoting her latest production projects and film roles, she prefers to keep her personal life to herself.

After her long-time partner, Bryan Randall, died in 2023, though, people couldn’t help but feel interested in The Proposal actor’s love life. To save you from myriad Google searches, we went ahead and did the sleuthing for you. Ahead, find a full rundown of the 59-year-old actress’s love life.

Tate Donovan

Sandy B met Tate Donovan on the set of Love Potion No. 9, which began filming in 1990 and premiered in 1992. Back in 1995, Sandra revealed to Vanity Fair that she “chased [Donovan] like a dog.”

tate donovan and sandra bullock photo by ron galellaron galella collection via getty images
Sandra Bullock and Tate Donovan, 1994Ron Galella

The pair dated for a few years before calling it quits in 1994. Although they broke up, Sandra continued to view Tate as the love of her life.

"Everybody has one that is apart from all the rest … He brought out everything in me that was good, that was bad, that was suppressed," she told Barbara Walters in 1996. Then, in 1997, she told Rolling Stone, “You have one great love in life, and I've had it."

Troy Aikman

The Proposal actress took a break from actors and, in 1995, paired up with one of the most famous football players in the game (at the time), Dallas Cowboys quarterback Troy Aikman. This remains somewhat speculative, though, as Sandy B never actually confirmed their romance, she’s just been historically linked to the former football star and current NFL announcer.

Don Padilla

actress sandra bullock and boyfriend don padilla attend kelly kleins underworld book party on november 3, 1995 at the calvin klein store in new york city photo by ron galella, ltdron galella collection via getty images
Sandra Bullock and Don Padilla, 1995Ron Galella, Ltd.

In 1995, Sandra took Don Padilla, a film tech, as her date to The Net premiere. While little is known of their relationship, speculation swirls that he is responsible for helping her get over Tate. In a 1996 interview with Detour, she admitted to seeing someone for 10 months and noted that he was a “really sweet person.” "It's been rough because of all this that happened plus he's working all the time and I rarely get to see him,” she added. “But 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."

Matthew McConaughey

sandra bullock and matthew mcconaughey photo by magma agencywireimage
Sandra Bullock and Matthew McConaughey, 1997Magma Agency

Sandra moved on to dating her A Time to Kill co-star, Matthew McConaughey in 1996, though, in typical Sandy B fashion, she kept it under wraps. Although the pair split in 1998, she continues to hold Matthew in great respect. “It’s the work we both put in—there’s a great amount of respect and love,” she told Cosmopolitan in 2003. “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.”

Bob Schneider

bob schneider and sandra bullock attend the bambi awards 2000 in december, 2000 in berlin, germany photo by gisela schobergetty images
Sandra Bullock and Bob Schneider, 2000Gisela Schober

From 1999 to 2001, Sandra dated Austin indie-rocker, Bob Schneider. “As celebrities go, Bob and I have a very low-key relationship,” she told in 2000. “It’s something I learned through trial and error.”

Ryan Gosling

Sandra found herself linked to Ryan Gosling from 2002 to 2003 following their time on set together for 2002’s Murder by Numbers. In an interview with Cosmo, the Gravity actress revealed that Ryan had a way of bringing her back down to earth, noting that he taught her "to chill. 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."

sandra bullock, ryan gosling during after party for murder by numbers premiere at michaels in new york, new york, united states photo by sylvain gabouryfilmmagic
Sandra Bullock and Ryan Gosling, 2002Sylvain Gaboury

Years after their relationship fizzled out, the duo continues to hold each other in high regard. In a 2011 interview with The Times, Ryan called Sandra one of the “greatest girlfriends of all time.”

Jesse James

west hollywood, ca march 07 actor jesse james and actress sandra bullock arrive at the 2010 vanity fair oscar party hosted by graydon carter held at sunset tower on march 7, 2010 in west hollywood, california photo by ethan millerwireimage
Sandra Bullock and Jesse James, 2010Ethan Miller

After dating her way through the ‘90s and early ‘00s, Sandra met West Coast Choppers founder Jesse James and instantly hit it off. They got married in July 2005 and even began the adoption process for her son, Louis, in January 2010. However, following infidelity allegations that year, they divorced in June 2010. He eventually admitted to the allegations, telling Daily Mail in 2017 that, “Yeah, I did cheat on my wife, yeah. I stood up and took accountability for it and apologized. And that’s [the] end of story.”

Chris Evans

west hollywood, ca february 26 exclusive access special rates apply no north american on air broadcast until march 1, 2012 chris evans and sandra bullock attend the 2012 vanity fair oscar party hosted by graydon carter at sunset tower on february 26, 2012 in west hollywood, california photo by kevin mazurvf12wireimage
Sandra Bullock and Chris Evans, 2012Kevin Mazur/VF12

Although rumors swirled that Sandra and Chris Evans were an item in 2014, Sandy confirmed that they were just friends. Nevertheless, Chris told E! News and Playboy that she was his childhood celebrity crush. “I used to be in love with Sandra Bullock when I was growing up—Sandy B. was my girl,” he told Playboy.

Bryan Randall

new york, ny june 05 sandra bullock and bryan randall are seen at oceans 8 world premiere on june 5, 2018 in new york city photo by jackson leegc images
Sandra Bullock and Bryan Randall, 2018Jackson Lee

Sandra began dating photographer Bryan Randall after he photographed her son Louis’s birthday party. The pair dated for eight years but never got married. Tragically, Bryan died at the age of 57 in August 2023, following a private 3-year battle with ALS.

You Might Also Like