Walk of Fame Celebrities And Their Surprising Exes Published 3 years ago on May 11, 2016 By Carolyn Guerrero Celebrity romances are the biggest love for all of the tabloids. It’s always huge, gossipy news, and it sure sells! Whether it’s a celebrity breakup or a new celebrity romance, people love to hear about it. Being in the media all the time, though, romances don’t always work out! Here are some celebrity romances that fizzled out, and now surely are being regretted! 19. Gerard Butler & Jessica Biel Both Butler and Biel appeared in the movie Playing for Keeps, a movie about a soccer-playing dad that’s attempting to re-ignite his passion with his ex-wife, played by Biel. WENN While filming, the two dated, but Butler called things off when he got frightened off by Biel’s serious romantic intentions with him. Nowadays, of course, Biel is married to Justin Timberlake, and Butler has said that not getting serious with Biel is one of his biggest regrets! 18. P. Diddy & Cameron Diaz Cameron Diaz is currently married to Benji Madden, and they have been married for a year, though they’ve dated for longer! WENN When the news broke about this celebrity couple, P. Diddy was overheard while he was having dinner, saying he seriously regretted losing Diaz. “If I could turn back time, things would be different,” sources reported him saying. 17. John Stamos & Lori Loughlin Stamos and Loughlin were both stars on the hugely popular television show Full House, so they got to know each other pretty well on set! Now, Stamos regrets his decision to not have taken it to the next level. WENN In an interview, Stamos said, “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.” 16. Lyndell Locke & Beyoncé Once upon a time, this couple was a thing… and you can sure bet that Lyndell Locke regrets his decisions! He definitely didn’t put a ring on it soon enough… Twitter Locke cheated on the talented singer, and lost her love. Now, she’s married to Jay-Z and they’re the ultimate power couple. Oh well, Locke lost his chance! 15. Zac Efron & Vanessa Hudgens “There’s not a star in heaven that we can’t reach…” Except, of course, this couple broke up. The two dated back during their High School Musical days, and were the ultimate Disney power couple. WENN After four years of dating, the couple broke up due to Efron’s intense partying lifestyle in 2010. Nowadays, each of them seem much happier, but their days together are definitely over… Bet these celebrities are sure regretting their decisions! Who else is on the list? 14. Clint Eastwood & Barbara Walters The saddest love story: “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.” WENN Now, Barbara regrets not having become Eastwood’s love. She tried to make some advances during the premiere of Jersey Boys, but sadly, it didn’t work. 13. Whoopi Goldberg and Ted Danson The Cheers star’s love affair with his Made in America costar caused quite a scandal in 1992. ca.complex.com/ The two had a wonderful, loving relationship with one another, and everything seemed to work extremely well, beside the fact that Danson was still married to then wife, Casey Coates at the time. The marriage obviously ended, but so did Danson and Goldberg’s romance. We’d love to see them back together, though! 12. Natalie Portman and Jake Gyllenhaal These two T-listers probably made one beautiful couple back in 2006, when they dated for a few months. www.eonline.com/ Though Portman is now happily married to Benjamin Millepied, and Gyllenhaal is considered to be one of Hollywood’s hottest and most eligible single men, the two remain close friends to this day. Hold on tight, some of the most shocking celebrity exes are still on the way! 11. Sean Penn & Madonna Sean Penn and Madonna were the hottest couple back in the day, and were even married for a time! But, in 1989, they divorced. WENN Madonna has said multiple times that Sean Penn is the one that got away, but the two had such an awful marriage, perhaps it’s better that they ended things! 10. Robin Thicke & Paula Patton This celebrity break-up was all over the news, and their messy divorce proceedings still haven’t even ended! This duo started off as high-school sweethearts, but that all ended not so long ago. WENN After Thicke’s Blurred Lines was released, Paula got wind that Thicke had been playing around and decided to leave him immediately. Thicke even wrote a whole album for her, entitled Paula. 9. Prince Harry & Florence Brudenell-Bruce Who wouldn’t want to date Prince Harry, right? You’d think dating royalty would be the best thing ever, but it’s not always what you’d expect. WENN/Instagram Prince Harry lost his love Florence when she couldn’t handle all of the media attention that came with dating a Prince. She eventually broke up with him, and now Prince Harry is single again! 8. Mario Lopez & Eva Longoria These two celebrities were BFF’s, and after Lopez suffered from a bad breakup, he wanted to turn his close friendship with Longoria into a little something more. WENN It seems Lopez got stuck in the friendzone! But it’s alright, because the two of them are now married to their respective partners, and they’re still close friends! So many celebrity couples that could have been! What other couples are listed? 7. Bradley Cooper & Jennifer Lawrence Jennifer Lawrence has been linked to several different celebrity love interests throughout the course of her career, including Bradley Cooper, though she insists they’ve always been friends. WENN Cooper is definitely in love with Lawrence, and now that Lawrence and Chris Martin have stopped dating, he might step up as a potential love interest! 6. George Clooney & Lisa Whelchel George Clooney used to be the eternal bachelor, but no more! He’s currently married, but that doesn’t mean that he didn’t used to date around. WENN The two worked together during The Facts of Life, and Whelchel has spoken up about that time, saying, “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.” Too late! 5. Geri Halliwell and Russell Brand As it turns out, the two Brits were an item back in 2012, after the Spice Girls reunion during the London Olympics. ca.complex.com/ They were spotted walking the walk of shame not long after the funnyman separated from former wife, Katy Perry. Needless to say, both the Ginger spice and Brand’s fans were pretty confused by this coupling. Wonder if they still have feelings for eachother! 4. Chelsea Handler and 50 Cent Another celebrity couple that threw everyone off was this funnywoman Chelsea Handler and badass rapper Curtis James Jackson III, AKA 50 Cent. Everyone assumed Handler’s infatuation with Jackson was part of her act, but the two ended up being an actual item. ca.complex.com/ For a short time in 2010, Handler reportedly couldn’t get enough of the rapper who survived nine different gunshot wounds, and talked about him on her show constantly. The couple eventually split, but remain good friends to this day. 3. Tyra Banks and Will Smith Now this is a celebrity power couple that could have produced some beautiful, fierce babies. Back in 1993, Banks was the ultimate super model, and Smith was both a successful musician and TV star, with his huge hit, The Fresh Prince of Bel Air. ca.complex.com/ The couple dated for two years but ended up going their separate ways. They do have a nice reminder of their young romance, though, in the eight episodes that featured Banks alongside the Fresh Prince. The next former celebrity pairing is going to give you quite a shock! 2. Cher and Tom Cruise Well, what do you know. The flamboyant singer and Scientologist actor were an actual couple for a short time during the 1980’s, and boy do we wish someone gave them a reality TV show. ca.complex.com/ The 16 year age gap didn’t bother them much, nor did Cher’s eccentric sense of style. Wonder if Cher would turn back time to rekindle her romance with the Mission Impossible star… Yeah, we went there. 1. Will Smith & Pepa Smith seems to be quite the heartthrob. These two seem like they’d be an odd couple, but back in the day, Will Smith was totally smitten for Pepa! Unfortunately for him, she wasn’t interested. WENN In an interview, she said, “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.” SHARE this article if you knew about the celebrity couples on this list! 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