It's Time to Revisit Sandra Bullock's Iconic Dating History, Y'all

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·6-min read
It's Time to Revisit Sandra Bullock's Iconic Dating History, Y'all
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While you're probs familiar with Sandra Bullock's extensive AF filmography (she'll always be Gracie Hart to me), you mayyyy not be as well acquainted with her dating history. Save for all that Jesse James drama—which was truly ugh—our silver screen queen has largely kept her love life out of the limelight...and in fact, you may not have even realized she's been with her current BF since 2015 (!!).

But before we get into her current romance, let's take a walk down memory lane and revisit the ghosts of Sandra Bullock's boyfriends past—including some veryyyy unexpected celeb guests. (Uh...Chris Evans??) Without further ado, Sandy's many lucky suitors over the years.

Tate Donovan: 1990 to 1995

For nearly four glorious years, Sandy was one-half of the '90s power couple that was herself and Marissa Cooper's dad. She and Tate met while filming Love Potion No. 9, fell in lurveee, and were even planning on tying the knot before they called off their engagement in 1995. And based on what Sandy told Vanity Fair in 1995, it seems like things didn't end well. ("I can’t explain why things worked out the way they did. We both know why it happened." The shade is real.)

Photo credit: Ron Galella, Ltd. - Getty Images
Photo credit: Ron Galella, Ltd. - Getty Images

However! The romance did lead to a beautiful friendship between Sandy and another one of Tate's exes, Jennifer Aniston. (Ever heard of her??) As she recounted to Jen during her 2020 Interview cover story, "We were introduced by our former boyfriend. I say ‘our’ because you and I both partook of this one human being. We both partook of Tate…who was a very patient human being, given that he dated us both." C-R-Y-I-N-G.

Photo credit: Charley Gallay - Getty Images
Photo credit: Charley Gallay - Getty Images

Thanks for this, Tate.

Troy Aikman: 1995 and 2014

While little is known about this possible romance, Sandra miiiight have dated the former Dallas Cowboys QB back in 1995...and apparently, they briefly rekindled things following her divorce in 2014 (more on that later). OK, Sandy!!

Photo credit: The Sporting News - Getty Images
Photo credit: The Sporting News - Getty Images

But that's all I know about that, soooo...moving on.

Don Padilla: 1995 to 1996

Okay, this one also isn't confirmed, but everyone's convinced Sandy dated this rando film tech because they attended the premiere of her 1995 flick The Net together—which is enough evidence for me.

Photo credit: Jim Smeal - Getty Images
Photo credit: Jim Smeal - Getty Images

The two reportedly dated for just under a year, and a 1997 Rolling Stone profile recounts Sandy having some ~issues~ on the set of A Time to Kill because of "the impending breakup of her relationship with film technician Don Padilla." 👀

Matthew McConaughey: 1996 to 1998

Though she and her A Time to Kill costar apparently dated for two years, they never actually admitted it...until after it was over. Even though literally! Everyone! Knew!

Photo credit: Ron Galella, Ltd. - Getty Images
Photo credit: Ron Galella, Ltd. - Getty Images

Luckily, it seems like things ended on good terms at least. When asked by Cosmo in 2003 how she stayed pals with her ex, here's what Sandy had to say:

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.

And sure enough, it looks like Sandra is legit friends with Matthew's model wife Camila Alves.

Photo credit: Kevin Winter/HFA2013 - Getty Images
Photo credit: Kevin Winter/HFA2013 - Getty Images

You love to see it.

Bob Schneider: 1999 to 2001

Sandra's two-year relationship with the country singer was suuuuper chill, so little is even known about it. She said as much herself during a 2000 interview with Cinema.com, admitting, "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."

Photo credit: Gisela Schober - Getty Images
Photo credit: Gisela Schober - Getty Images

Alas, the actor and the country crooner weren't meant to be. 3

Ryan Gosling: 2002 to 2003

Yet another celeb relationship that was kept hush-hush until after the fact: Sandy and Ryan, everyone! After co-starring in Murder by Numbers, the two were apparently loved up for about a year—but when asked whether she and Ryan were "just friends" by Cosmo in this 2003 interview, Sandra played it coy. "If you were to add the word just, it would probably be a bit of a lie. So I'd say we're friends," she said. Say no more, Sandy.

Photo credit: Gregg DeGuire - Getty Images
Photo credit: Gregg DeGuire - Getty Images

Later, during a 2011 interview with The Times, per Us Weekly, Ryan referred to Sandra as one of the “greatest girlfriends of all time," soooo I guess they're on good terms?

Jesse James: 2003 to 2010

I guess I have to talk about this guy now. Sandra first met her future ex-husband while touring the set of his show Monster Garage with her godson, and they decided to say "I do" less than two years later in July 2005. It seemed like things were going swimmingly for the pair for almost five years—until multiple women came forward in March 2010 about their alleged affairs with Jesse. Big yikes.

Photo credit: Steve Granitz - Getty Images
Photo credit: Steve Granitz - Getty Images

By June 2010, the couple finalized their divorce, and Jesse later admitted the cheating claims were, in fact, totally true. “Yeah, I did cheat on my wife, yeah," he told the Daily Mail in 2017. “I stood up and took accountability for it and apologized. And that’s [the] end of story ... In general, both women and men cheat. It's part of life." Yeah, no.

Chris Evans: 2014

After the Jesse drams, Sandy (understandably) took a lil break from dating, but she made headlines in 2014 after sparking dating rumors with Captain America. The unlikely duo first crossed paths at a Vanity Fair Oscar party in 2012, and not long after, Chris admitted to crushing on the actress as a kid. "I used to be in love with Sandra Bullock when I was growing up. Sandy B. was my girl," he told Playboy. "I remember seeing Speed when I was in seventh grade and just thinking, 'That's her.'" BRB, dying.

Photo credit: Kevin Mazur/VF12 - Getty Images
Photo credit: Kevin Mazur/VF12 - Getty Images

They went on to (maybe?) date two years later, but it seems like things were short-lived. As a source claimed to E! News in May 2014, "They are not in a relationship, but they are definitely hanging out and are in the early getting-to-know-each-other phase. They haven't put a title on it, but they really like each other." Le sigh.

Bryan Randall: 2015 to ???

Which brings us to Sandra's current beau, photographer Bryan Randall. The couple apparently met back in 2015 when Bryan photographed her son Louis’ b-day bash (what a meet-cute!) and have been going strong ever since...though she makes sure to keep her relationship far, farrrr away from the paparazzi.

Photo credit: Jackson Lee - Getty Images
Photo credit: Jackson Lee - Getty Images

As of May 2021, Sandy and Bryan are "doing better than ever" (according to a source for Closer Weekly, anyway), and while it doesn't seem as though the two have any wedding plans, if Sandra is happy, then I'm happy!!

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