Watching Jimmy Fallon lose it when he realized he missed his one-and-only chance with Nicole Kidman was one of the funniest moments on TV this week. But Jimmy’s not the only celebrity who lost his big chance. Check out our list of celebrities who regret the one who got away.
Gerard Butler and Jessica Biel
Gerard and Jessica dated while filming the rom com Playing for Keeps, but Gerard bailed when Jessica’s serious intentions temporarily frightened him.
Now Jessica’s married to Justin Timberlake and Gerard has been telling the tabloids that not getting serious with Jessica when he had the chance is one of his biggest regrets.
P. Diddy and Cameron Diaz
Once the news of Cameron Diaz and Benji Madden broke, Diddy was overheard at dinner saying that he seriously regrets not getting serious about Cameron saying “If I could turn back time, things would be different!”
That has to be awkward for Cassie.
John Stamos and Lori Loughlin
Not every celebrity is willing to let the one that got away stay gone.
John Stamos has been letting slip that he regrets not taking his fling with his Full House co-star Lori Loughlin to the next level:
“We did have some off timing, but no disrespect to her family and her husband now, I would say that she could be the one that got away. She’s one of my dearest friends and that’s good enough. But I really do adore her. She has a great husband and he’s got a lot of money.”
Is it just us or is John firing low-key “I want her back” shots at Lori’s husband?
Lyndell Locke and Beyonce
There’s a reason this brother is the patron saint of lost loves. No one has bigger romantic regrets than the man that cheated on Beyonce and then lost her to Jay-Z.
Zac Efron and Vanessa Hudgens
Vanessa Hugens was Zac Efron’s first love but after four years, Zac’s partying ways broke the couple up in 2010.
Now that Zac is out of rehab he’s finding it hard to accept that Vanessa is gone and his unresolved love for her is why he keeps jumping back from fling to fling.
Barbara Walters and Clint Eastwood
Sometimes you have to strike while the iron is hot. Barbara shared her story of what could have been with Jimmy fallen:
“This is a sad love story. I did this interview with Clint Eastwood something like 30 years ago. He was very flirtatious, and I was very taken (with him). He asked me if I wanted to have dinner … and I said, ‘No, I have to work.’ You know, I don’t mix business with pleasure.”
Barbara says she went on to regret not becoming “Mrs. Clint Eastwood” for years. Then recently she decided to take a second shot at the premiere of Jersey Boys. But Barbara says despite the fact that she got dressed up for the occasion, it was too late: “He was … polite. He was courteous. What’s that expression? He was just not (that) into me.”
Sean Penn and Madonna
After their divorce in 1989, Madonna has often said that Sean Penn was the one that got away. But considering those two’s volatile and violent marriage it’s probably better that Sean stays gone.
Paula Patton and Robin Thicke
The dust hasn’t yet settled on the divorce between these two high-school sweethearts. But we bet that a few years down the line when Robin’s gotten the player out of his system that Paula will be the great love-regret of his life.
We also bet that the heartbroken songs in Paula Pt. 2 will be chart toppers.
Prince Harry and Florence Brudenell-Bruce
Sometimes even royalty isn’t all it’s cracked up to be.
Prince Harry lost the love of his life, socialite Florence Brudenell-Bruce, because she couldn’t stand the media attention. So she broke up with Prince Harry and married her ex-boyfriend in the South of France.
Eva Longoria and Mario Lopez
Even celebrities get stuck in the friend zone.
After one bad breakup, Mario Lopez recently admitted that he wants his close friendship with Eva Longoria was something more. But it looks like there’s nothing but BFF’s in the cards for these two celebrity friends.
Mario even walked Eva’s mother down the aisle during her wedding to Tony Parker. And now they’re both booed up to other people.
Bradley Cooper and Jennifer Lawrence
Everyone is dying to know who Jennifer Lawrence is going to end up with next after breaking it off with Chris Martin.
And even though he’s dating Suki Waterhouse, sources close to Bradley Cooper told OK! magazine that he regrets not stepping out of the friend zone with his celebrity BFF Jennifer Lawrence.
They do look cute together…
Lisa Whelchel and George Clooney
These two were on set together during The Facts of Life. Lisa says if she knew that now-married George was going to grow out of his gawky stage she would have put in a little more effort on set:
“I don’t know, maybe I was just not smart, or not thinking ahead, because I did not anticipate what he would grow into. I think if I had, I would’ve worn makeup to rehearsal a little bit more often.”
We don’t blame her for passing up on that opportunity!
Pepa and Will Smith
Pepa and Will Smith?
Apparently, Will Smith was into Pepa back in the day but she wasn’t interested:
“I thought Will was really cute and we would hang out a lot on the road. He liked to take care of me and never let me spend a dime. He was that kind of guy, real generous.
I remember when they won their first award, he asked me to go out with him afterward. He was so excited. We were walking along the street getting ready to grab something to eat, and he just gave this homeless guy $100 dollars…I sometimes kick myself when I think about what could have been.
He was so nice to me, but I really wasn’t feeling him. I guess I couldn’t appreciate a nice guy like Will Smith. He wasn’t thug enough. I was attracted to thugs and hoodlums. Will was too nice to me.”
We’d be kicking ourselves too…