How a Devastating Divorce Led Sandra Bullock to True Love

Following ex-husband Jesse James' heartbreaking infidelity, the Oscar winner found her "soulmate" in photographer Bryan Randall.

By Sarah Grossbart Jul 26, 2018 10:00 AMTags
Sandra Bullock, Oscars 2010Jason Merritt/Getty Images

By her early thirties, Sandra Bullock was already weary from the whole, complicated looking-for-love process. She was seeing someone, "really sweet," she told Dennis Hensley in a 1996 interview for Detour (presumably film tech Dan Padilla, her date to the 1995 premiere of The Net), but getting to that point had been rough. "For a year I was by myself trying to date and I'm telling you dating was the worst experience I ever had," she confessed. "I seem to have attracted everyone whose intentions were not the best."

It's not so much that they were after a slice of her growing fortune or her very much on-the-rise fame (though she said one suitor's ex-girlfriend sold a story claiming he was trashing her character), "Just people who's intentions were so not in tune morally with mine," she clarified. "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."

Sandra Bullock's Romantic History

And this was a whole decade and a half before the saga that was Jesse James

Recovering from the West Coast Chopper owner's exorbitant infidelity (not to mention the cavalier attitude that would lead him to declare that cheating is simply "part of life,") at a time she was supposed to be celebrating her Oscar win and the adoption of her first child, now-8-year-old son Louis, was, to put it lightly, devastating for the Virginia native. "She was embarrassed by what he did and in ways blamed herself at the time," an insider told E! News last year. "She did consider Jesse a father to Louis, so that was one of the hardest parts of breaking up." 

But after spending years focused on her children—now-6-year-old Laila joined her brother in 2015—and enough time spent on her film career to garner another Academy Award nomination, she finally took the advice she had spouted in the same 1996 article, the old adage about how the best way to get over someone is to meet someone new. "I'm not saying go out and sleep with them," she noted. "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.'

Jeffrey Mayer/Getty Images

At 54, the age she's somehow turning today, she's found more than just a piece of eye candy. (Though she and Bryan Randall are quite the striking pair.) The Portland, Ore. native, a model before he formed his own lifestyle photography business, is the type of man she always desired, the person, as she once described to Entertainment Tonight, "you can admire and be proud of and sit back and go, ‘this is my man.'" 

More than three years in—when the pair were first spotted out in August 2015, they'd already been quietly dating for months—she's still bursting with pride. "They are soulmates," one source asserts to E! News. "Their love is pretty deep and intense." 

Clint Brewer/TC/Splash News

We're willing to bet Randall fills out the rest of the informal checklist Bullock put forth to ET back in 1999: "a man who can make you laugh and think, can really stimulate you and excite you when you're gone," but his most winning asset is his skill with chidlren. 

It's a talent that was put to the test early, what with Randall reportedly crossing paths with America's reluctant sweetheart ("I think I lost that title a little while ago," she joked to Cosmopolitan in 2003) when he was booked to photograph Louis' fifth birthday. And it's one he's proven time and time again to the devoted mother. "Sandra's favorite thing is to be a mom and take care of Louis and Laila," a source told E! News. "It's her biggest joy in life." 

Sandra Bullock & Bryan Randall's Romance Timeline

Randall, father to his own adult daughter, keyed in on that early, understanding that a prerequisite of dating Bullock was getting in with the tot she once dubbed "the only man in my life." He quickly embraced his father figure role, says a source, treating the actress' kids "like his own." 

It's a part he may have played just a little too well considering Bullock's recent confession to InStyle. "He's super kind. For the kids he's sort of No. 1 and I'm No. 2," she admitted in the mag's June issue. "But I get it because he's more fun and has better treats."


Though Randall innately understands that fatherhood extends far beyond a riveting game of hide-and-go-seek and a few extra pieces of candy. "He's involved with their school work, he goes to all of the kids birthday parties and he is always by Sandy's side with whatever she needs," reveals a source. "They have built a great life together and the kids are the centerpiece."

And their dearest, most prized treasure. During what Bullock calls the "tenuous, strenuous" six-month placement period with Laila where "if something goes sideways, they have the right to take the child away," he helped the Gravity star keep their little secret, well, secret. 

"We had an allergy scare that sent us to the ER, and we were followed by the paparazzi, so the word was out that I had another child," she told InStyle. And everyone wanted photos." As little Louis jumped into protector mode ("It was heartbreaking," she recalled. "Louis would hear a helicopter or drone, and he'd run to get his sister and drag her across the lawn and hide her under the trampoline,") and Bullock enlisted a team of lawyers to keep any pictures unpublished, Randall was her rock.  

Sandra Bullock's Best Looks

"Bryan has been an amazing support system to her and Louis," a source told E! News in September 2015, before it became clear why she might need a little extra encouragement. "They are completely in love."

When it became time to reveal Laila to the world, he was front and center, accepting the tricky task of capturing his girlfriend and her two kids for the cover of People. Bullock chose not to show her face "because there was a bounty on our heads," so the job was a challenge, she admitted to InStyle, but thankfully, "He's a patient photographer."

FH/GC Images

So, yeah, his list of attributes is protracted enough to deem him worthy of a woman so darn likable that fans can't stop giving her awards. (She has 10 People's Choice trophies to go with her SAG, Golden Globe and Oscar honors.)  

While he's certainly proud of her achievements, even making a rare appearance at her 2015 Our Brand Is Crisis premiere, "He won't ever be that dude that wants the spotlight or walks the red carpet," notes an insider. (No questionable intentions? Check.) Continues the insider, "They have a very down-to-earth relationship."

Though Bullock is one of the industry's most bankable stars (hello, Ocean's 8!) she doesn't revel in all of the trappings that come with her fame. A good enough sport to accept her dishonorable 2010 Razzie for All About Steve the day before she won Oscar gold ("If you take either one too seriously, shame on you, and if you disregard the other because it's not all you want it to be, then shame on you too," she told The Guardian that year) she says in the grand scheme her career is "meaningless and empty." (To be clear: She's talking about the part where she pretends for a living, not the part where she funnels those earned millions to the Red Cross and other worthy causes.) 

"I'm not wary of it, though—I'm just aware," she said of fame. "It holds nothing for me, although it will hold a great table in a restaurant, when you're at your peak. If you don't have other real things in your life that you love just as much, then you will drown in it."

Clint Brewer/TC/Splash News

Staying afloat is no issue for Bullock, who knows her true happiness is at home—whether that's her Beverly Hills Tudor-style mansion, her Victorian in New Orleans, her oceanfront hideaway in Georgia, her New York City townhouse or the Wyoming chalet where she and Randall took the kids last year

"Sandy leads a normal life and really separates herself from the Hollywood hype when she is not promoting a movie or shooting a film," says an insider. "One of her favorite things to do is stay home with her kids and Bryan."

And to hear Bullock rave about her little crew, it's hard to fault her for not wanting to miss a moment. "Lou is supersensitive," she told InStyle. "I call him my 78-year-old son. He's like Shecky Greene, a Jewish Catskills comic. He's wise and kind. I saw that when they handed him to me. There was a spiritual bigness to him. I was like, 'I hope I don't eff that up.'" And Laila is a pioneer in the making. A fighter, says the star, she marvels at what the grade-schooler is destined to accomplish: "She's going to bring some real change." 

Of course, much like any parents of young kids, the couple do carve out some time as a party of two. (We're guessing their days as Jennifer Aniston and Justin Theroux's favorite double date companions are now over.) And whether it's morning coffee or a dinner at one of those aforementioned great tables, says a source, "They don't leave each other's side."

Sandra Bullock's Best Roles

It's looking increasingly unlikely that they ever will. While they've yet to run off and quietly get hitched (because been there, done that), they have one of those pretty-much-married-except-for-the-paperwork relationships. 

"Bryan is not only her partner but also her best friend," raves one insider. "They seem like they've been together forever when you're in their presence." 

JosiahW / Gachie / Splash News

Or perhaps it just feels as if it took that long to get here. But had Bullock been listening to her own prophecies, she would have had no doubt this day would come. 

As she said back in 1996, "I'm a true believer in karma. You get what you give whether it's bad or good."

And she was due for someone truly, amazingly, unquestionably good.