Sandra Bullock's Romantic History: The Rumors and the Reality, Including the Relationships You Totally Forgot About

Just like when you're watching one of the Oscar winner's movies, you may be charmed all over again (and definitely creeped out at one point) when you remember some of these moments in her dating past

By Natalie Finn Aug 08, 2017 11:00 AMTags
Sandra BullockPeter Kramer/NBC

Sandra Bullock once famously said that she'd be the first person to recommend not dating her, "because I'll probably make you miserable."

Big surprise, no one took that seriously for a second.

The Oscar winner, once divorced and now happily ensconced in a live-in relationship with photographer Bryan Randall, has been a huge star for almost 25 years—meaning, she's been fielding questions about her personal life for just about that long.

By now she's sat through interviews at every stage of the romance game, through the ups and the downs, when it was real and when it was just a passing rumor, during the honeymoon phase and then in the thick of the postmortem after it all went wrong.

But through the majority of it, Bullock was refreshingly candid and often endearingly self-deprecating (see above quote) about dating and breakups (though she wouldn't usually say much while a relationship was ongoing). Better yet, she's almost never met a trumped-up report that she didn't relish poking fun at, making it easier to keep the reality and the rumors straight.

In 1999, asked by Entertainment Tonight if she felt there was that one person out there for her her, she smiled and shook her head, feigning emotional distress and squealing, "I don't know!"

Admitting that at one point she was "deathly afraid of marriage," she said she'd learned a lot about love and what it meant to love someone. The Hope Floats star mused, "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...Who care how much somebody makes for a living? In the end we're all going to be old and wrinkled. You'd like to know that that person can, a, make you laugh, and think, you know can really stimulate you and excite you when they're gone and you think about them. Somebody you can admire and be proud of and sit back and go, 'this is my man.'

And whether or not he's a millionaire, or he's a painter, a musician, or somebody who just, you know, shucks clams, it's that respect level that we forget to look for."

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There haven't been any clam shuckers in the mix (not professional ones, anyway), but when Bullock was just kinda doing her her thing in the dating department and making her way in Hollywood, she was a wellspring of information.

She revealed to Detour in 1996 that her first-ever boyfriend's initials were G.D., though she withheld his name from the record. "Red hair. Irish. I have a thing for red haired Irish boys as we know," she quipped. (Yeah, Tate Donovan was kinda gingery back in the day...)

Over the years, she has candidly admitted to having once sent herself flowers to jog a guy's interest in her (it worked), to a pattern of not attracting guys with the best intentions, to her tendency to put the guy first and herself second, and to her belief in the adage that the best way to get over someone is to meet someone else. 

"I'm not saying go out and sleep with them," she clarified to Detour. "I'm just saying go out and have a conversation and know that they find you attractive and go, 'Okay, I'm not the piece of trash that I thought I was two days ago.' Allow yourself a week or two to eat bonbons and be depressed but then make your friends take you out. The worst parts of being dumped or breaking up is the night time, going to sleep and wanting to fall asleep and wondering where they are every second of the time."

That being said, Bullock didn't believe that rebounding was going to solve all her problems. Or she eventually arrived at that conclusion.

Mark Davis/WireImage for Spike TV

She told in 2000, "I don't need a man to be happy. But it takes some time to realize that. I don't need to find a man to progress as a human being. I'd do it with him. And if I happen to outgrow him, or he outgrows me, that's what happens. I've never been in a place that I couldn't get out of. Yes, sometimes you stay in a place for a while because you're trying to figure out. You wonder whether you're going through a phase, or whether something is really not working, or if it's just another hill."

Bullock has also dated a few of her co-stars, admitting to Cosmopolitan in 2003 that movie sets are "breeding grounds for that kind of stuff, so you just have to have a good set of rules going into it." (No. 1: stay away from the co-stars who are in relationships.)

"It's the greatest dating service on the planet," she said. "You take two people who normally can't leave the house, who don't know if people are with them for the right reasons, and they get paired up because they have chemistry, and they happen to fall in love."

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Not exactly excluding actors from the picture, she also told the mag, "I love people who are artistic, confident, and even cocky but with an underlying modesty that is humbling. They also have to have a wicked sense of humor, and I have to feel challenged. If somebody does not swat it right back to me, I'll get bored."

But in 2010, when she nearly simultaneously got divorced and became a mom, there was a definite shift in how Bullock approached talking about herself and how much she was willing to share about her personal life. Because after son Louis arrived, he was the man in her life, and mother and child's privacy was paramount. (Though, praise be, she still loves laughing at rumors.)

So here's a walk down relationship-memory lane, with Sandra herself as our guide:

Tate Donovan

The Damages star was one of the great loves of Bullock's early-Hollywood life after they met in 1990 on the set of Love Potion No. 9, which didn't get to theaters until 1992. They broke up in 1994 and, not long after, Donovan started dating Jennifer Aniston.

"I adored Tate so much," Bullock told Vanity Fair in 1995, her voice reportedly trembling with emotion. "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. There's nobody that means more to me, and I know for a fact that I mean the most to him, in that certain way. I can't explain why things worked out the way they did. We both know why it happened." 

"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, explaining how she had always held people at arm's length prior to dating Donovan. Asked if she was over the relationship, Bullock said, "I don't think you ever get over something that is honest...It takes a lot for me to fall [in love]. A lot. And knowing him was the greatest gift to myself and to my personality—and to my work, in sort of opening the door."

The actress shot down Walters' suggestion that perhaps it was her fame surpassing Donovan's that helped bring about the end. "Never in a million years do I think that success is what pushed a love away," Bullock countered. "That's not it at all. And it doesn't go away. It stays in its very special place. It's always something that'll be taken care of and I respect it, and I protect that more than anything, and I won't let anybody cheapen it. Because two good, honest people, just because it doesn't work doesn't mean they can't stay doesn't make anybody the bad guy. We both made mistakes and you've got to go on."


Asked if she wanted to be married, the then 30ish-old Bullock (she used to play coy about such things way back in the day), told Walters, "I'd love to be in a place where I go, 'I'm ready to be married.'" But she wasn't ready then. (And she also said she'd never yet been engaged, though some reports have called Donovan her ex-fiancé.)

Donovan told E! News in 2010, after seeing both Bullock and Aniston at the Golden Globes that year, "I mean, it's been 150 years, so if you can't bury hatchet in that amount of time something's wrong with you."

Troy Aikman

When Bullock was blinked-and-you-missed-it linked to the NFL Hall of Famer in 2014, that wasn't their first time sharing column space. Fresh off the success of Speed, the actress was linked to Aikman back in 1995, too, when he was still the Dallas Cowboys' superstar quarterback.

Vanity Fair broached the rumor, but she shook her head, saying, "I don't want to put myself in the dating category."It's going to be a long time before I can trust anyone again. I don't know anybody who'd want to get involved with me right now, and be put through all the strain, because I have no idea what all the repercussions might be. I couldn't possibly imagine anybody wanting to be there unless they were a thrill seeker." She added, smiling, "But if somebody does, and they're really secure with that, and they want to be in my life for the long haul, like a 12-year dating process before we start really seeing each other..."

Don Padilla

The film tech was Bullock's date to the July 1995 premiere of The Net—and though she had told VF around then that it was "going to be a long time before I can trust anyone again," it sounds as though Padilla have been the guy who helped Bullock out of the Tate Donovan doldrums.

Talking to Detour in 1996 in Jackson, Miss., where A Time to Kill was close to wrapping production, Bullock admitted she'd been seeing someone for about 10 months.

"Really sweet person," she described the then-nameless lucky guy. "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. I seem to have attracted everyone whose intentions were not the best."

A June 1997 Rolling Stone profile recounts Bullock as having some professional and personal issues on the set of the legal drama as well, in part because of the breakdown of her relationship with Padilla.

"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 cryptically reflected to the magazine. "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."

Matthew McConaughey

Bullock told Detour that she had once sworn off dating actors, assuming they wouldn't have the best intentions, but "I generalized and it wasn't fair because I met some people that aren't that way."

These two were rumored to be the hot couple after co-starring in A Time to Kill (on which Bullock had used her blockbuster clout to help McConaughey land the job, which turned out to be his big break). But when the nearly two-year romance was unfolding, neither admitted to it in real time. 

On Oprah while out promoting 1997's Hope Floats, when asked if she was dating McConaughey (who also is said to have romanced Ashley Judd, who played his wife, during filming), she said, point blank, "No, we are not." But, she added jovially, "whatever woman gets him is going to have to get by me."

But by 2003, she didn't correct Cosmopolitan when McConaughey was referred to her as her ex-boyfriend.  Asked how they managed to stay friends, she said, "It's the work we both put in. 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."

Sure enough, they've remained friends (Bullock's been seeing hanging out with McConaughey's wife, Camila Alves) and he joined Keanu Reeves and Hugh Grant in feting the foxy star at the 2014 Guys' Choice Awards, when she was given Spike TV's Decade of Hotness honor.

Bob Schneider

During the nearly two decades when Austin, Texas, was her home base, Bullock quietly dated the Austin-based musician from around 1999 until 2001—but the union of his songs and her films transcended the time constraints of their relationship.

Schneider's song "Blue Skies for Everyone" is in Gun Shy, "Bullets" is on the Miss Congeniality soundtrack, "The World Exploded Into Love" is in The Divine Secrets of the Ya-Ya Sisterhood and "Love Is Everywhere" is one of the better things in All About Steve. (Kinda like she did with McConaughey, she's said to have helped put Schneider on the map.)

"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," Bullock dished to in 2000.

She admitted, "Dating is complicated for me. I have a fear of saying the L-word. Oh my God! I always feel like the minute I say it the sky will fall. I'm like, 'I lllllllllloooooo...'" she trailed off. "Love is a bad, bad thing! I've said 'I adore you,' and that was my way of, like, saying...because it felt the same and I meant exactly that...But then Bob and I talk German all the time to each other, which is terribly funny because I'm so bad at it. Maybe saying 'I love you' in German could be easier for me."

At the time, though, while on the verge of another hit with Miss Congeniality, she said, "I love working, but I also enjoy this nesting period I'm in...I've narrowed my dating prospects down to one person. Whatever happens, happens. I don't know what that will be, but there's so much joy now. So much joy."

Ryan Gosling

In 2003, the Cosmo interviewer noted that Bullock had never used the word "just," as in "just friends," when talking about McConaughey, because that would have been not quite truthful. If there was no "just," then they could technically be friends... who also happened to be dating. 

So when asked if she would describe herself and Gosling, her co-star in Murder by Numbers, as "just friends," Bullock said, "Let me see if I can answer that politically and correctly. We're friends." Adding "just" would "probably be a bit of a lie," she admitted. "So I'd say we're friends."

She said that Gosling had helped her, a self-professed OCD type, "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."

Jesse James

When Bullock married the Monster Garage biker on July 16, 2005, they were already the most adorable odd couple in Hollywood.

"No one knows what someone is like based on appearance," Bullock reminded People before they snuck off and tied the knot in front of friends and family who didn't know ahead of time they were going to a wedding. "There are people who look very innocent, loving and churchgoing who cheat on their spouses, don't take care of their children and are horrible to humanity."

The heavily tattooed West Coast Choppers owner, whom Bullock met while taking her nephew for a tour of his Long Beach shop, made for a pretty dashing red carpet date and he always seemed to be looking at his wife so admiringly from the crowd. James also seemed like a stand-up guy, getting scolded on Celebrity Apprentice for not hitting his Hollywood-star wife or her fancy friends up for money rather than name-drop.

About 10 days after Bullock won the Best Actress Oscar for The Blind Side in 2010, however, the world would find out that the star of Jesse James Is a Dead Man was actually just a jackass. Among other things, it turned out he'd been cheating on Bullock. Lots.

"This has caused my wife and kids pain and embarrassment beyond comprehension and I am extremely saddened to have brought this on them," James, a father of three with his first wife, said in a statement. "I am truly very sorry for the grief I have caused them. I hope one day they can find it in their hearts to forgive me." (Don't worry, he forgave himself.)

Days after she filed for divorce that April, Bullock introduced her son Louis to the world on the cover of People, revealing that she and James had been adopting Louis together until the reality star torpedoed their marriage. 

"We're all where we're supposed to be," she told Vogue in 2013. "I am exactly where I want to be now. You can't go backward. I'm not going backward." Louis has remained center stage, only now he has a co-star in sister Laila, whom Bullock adopted in 2015.

Ryan Reynolds

With all of the leading men in her onscreen life, it's a wonder that these sorts of rumors didn't trail her off-camera even more often.

So though their chemistry was off the charts in The Proposal, these two were also just buddies as well.

"Oh, my lovah? My new lovah?" Bullock nodded and feigned a romantic accent when Al Roker checked in with her on the red carpet at the 2011 Golden Globes about her and Reynolds. He had filed for divorce from Scarlett Johansson less than a month beforehand, and Bullock herself had been divorced for less than a year.

The actress jovially informed Al, "I think there will be a collective sigh amongst women in the United States when I say, he's not my lovah, he's just an amazing friend I've had for 10 years. And I hope there's more friendship like that, but I don't [returning to accent mode] get his loving after dark." Asked about her son, she smiled and agreed, "That's the only man in my life right now."

Chris Evans

Definitely friends, and a source told E! News the handsome pair "really liked each other" (what a stretch, right?), but Bullock insisted they were nothing more.

"You guys are a little behind," the actress told ET when asked about the dating speculation in June 2014. "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."

In March 2017, Evans told E! that Bullock was one of his big celebrity crushes, "like when I was in seventh or eighth grade."


Bryan Randall

After taking a nice long break from relationships to focus on her kids and, when she was so inclined, little work (enough to score her a second Oscar nomination, for Gravity), Bullock started dating the photographer and former model in 2015, after he had been hired to shoot Louis' 5th birthday party.

More than two years later, they're cohabitating and a source previously told E! News that Bullock was the "happiest she's ever been" with Randall, who also has a grown daughter.

And whose happiness in Hollywood should we be happier for than Sandra Bullock's?

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