Sandra Bullock is one of America’s sweethearts; she is charming, successful, and has often been compared to Lucille Ball, thanks to her comedic timing and talent. Breaking into ‘household name’ territory through movies like Speed, The Net, While You Were Sleeping, A Time To Kill, Miss Congeniality, and Two Weeks Notice, she has been acting steadily for nearly three decades.
Holding the title of highest-paid female actress in 2010 and 2014, and earning a spot as one of Time's '100 Most Influential People In The World', she is definitely one of the savviest career women in Hollywood. She won an Academy Award and a Golden Globe for her work and has received many other nominations and awards for her performances.
Like any career in the spotlight, romantic controversies, such as cheating scandals, can steal a performer’s thunder and eclipse even their greatest accomplishments. A highly-publicized incident in her life inspired her to keep her personal life to herself. Because of her more recent retreat into privacy, people are left wondering what’s going on with her romantic life.
Is Sandra Bullock single? Here's what we know about her relationships.
15 Putting Parenting First
Because Sandra faced a very public divorce at almost the exact same time as she adopted her son, Louis, privacy became very important to the star. She was determined to build the family she wanted and made a deliberate effort to be less open with the press, all for the sake of her son.
14 Missed Opportunities With Keanu Reeves
Bullock and Reeves have notably been in Speed and The Lake House together, but romance only happened when the cameras were rolling. While he was on The Ellen DeGeneres Show, Ellen revealed that Sandy had said she had a crush on Keanu in the past. Keanu, in his quietly confident way, let the world know that this was a missed connection, saying, “She obviously didn't know that I had a crush on her, either.”
13 Sharing A Dating History With Jennifer Aniston
Both Jennifer Aniston and Sandra Bullock have been romantically involved with Tate Donovan. Bullock met him on the set of a film in 1990 and they dated until 1994, with Donovan dating Aniston shortly after. Bullock spoke fondly of her ex, post-break-up, 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.”
12 The Truth Behind Ex, Jesse James
Bullock married Monster Garage biker, Jesse James, in 2005, and reminded people not to judge a book by its cover. People did have doubts about her relationship with him. Unfortunately, less than two weeks after her Oscar win, Bullock - and the world - discovered that James was cheating on his award-winning wife...a lot. Humiliated, Bullock divorced James shortly after the scandal broke.
11 Romance With Bryan Randall
When asked in 1999 if she thought there was one person for her, she quite candidly said, “I don't know!" and admitted that, at one time, she was afraid of marriage. Now, nearly five years into her relationship with Bryan Randall, it’s clear that she’s met someone who she wants to share her life with.
10 Blindsided By Troy Aikman
Long before Bullock was involved in an award-winning film about football, she was rumored to have dated Dallas Cowboys’ star, Troy Aikman. Bullock was repeatedly questioned about their romantic status in 1995 and would neither confirm nor deny whether things qualified as a fling, a friendship, or otherwise. She said, "I don't want to put myself in the dating category" with the athlete.
9 Says She Doesn't Need A Man To Be Happy
Bullock knows what she wants for her family and career, having clocked over 25 years as a success in the business.
Even back in 2000, she was so confident in herself: "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."
8 Swearing Off Dating Actors
After being burned by a couple of tough breakups from fellow industry professionals, Bullock said she would look for romance outside of her profession, swearing off fellow thespians. Bullock later softened her stance on issues with dating in the industry, saying, "I generalized and it wasn't fair because I met some people that aren't that way", according to E Online.
7 Killing Time With Matthew McConaughey
Because of their onscreen chemistry in A Time To Kill, the two were rumored to be dating on and off for two years. Neither would confirm anything more than a solid friendship.
She said of their chemistry, "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", according to E Online.
Today, Bullock remains friends with Matthew and has built a friendship with his wife, Camilla Alves.
6 Heating Things Up With Ryan Gosling
In 2003, Sandra Bullock had people talking because of her “May-December” romance with Ryan Gosling, who is 16 years younger. The two met on the film, Murder By Numbers, and Bullock was cheeky when questioned about the nature of their relationship.
She 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. So, I'd say we're friends", according to Cosmopolitan.
5 Just Friends With Ryan Reynolds
Just because there is an on-screen spark, it doesn’t mean that all actors pursue it. Despite fans everywhere wanting to declare ‘Reylocks’ a thing, the two were platonically friendly and nothing more.
When on the red carpet to promote their film, The Proposal, mere days after Reynolds' divorce from ScarJo, she jokingly called Reynolds, “my lovah?” in a humorous ‘romance’ accent.
4 Joking About Chris Evans
While some people really swoon for superheroes, Bullock is content with super friendships. When asked about romance with Captain America, aka Chris Evans, she decided to play with reporters.
She said, "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", according to People.
3 Step-Mom Moments
Sandra Bullock was a very involved step-mother to Jesse James’ daughter during their marriage. Unfortunately, when their relationship ended, so did Bullock’s connection with her step-daughter. People questioned Bullock’s rights and obligations to Sunny, and according to the law, a step-mother is "a biological and legal stranger to these children and has absolutely no rights to custody or visitation."
Jesse James moving to a different state probably didn’t help them maintain a relationship.
2 Taking Things Slow
Sandra Bullock waited until several years into her relationship with American photographer, Bryan Randall, before she brought things into the spotlight. This was likely because her public romances in the past have caused her nothing but grief. The pair met when Randall was hired to shoot her son’s birthday party - they decided to mix business with pleasure.
1 Tying The Knot?
According to sources close to Bullock, the star has said that she doesn’t need marriage to prove her love to the actor. A marriage to him would likely involve a prenup to protect Bullock's finances. Bullock got lucky when she divorced ex, Jesse James, in 2010 - he didn’t qualify for any alimony or settlement.
Even though the pair aren’t married, it’s said that Bryan now proudly wears a ring on his finger to show his commitment to their relationship.
Sources: Ace Show Biz, Closer Weekly, Ranker, People, Marie Claire, Psychology Today