Oh, how we love our Hollywood golden couples, pairings that seem so effortless. We all marvel at how they make celeb partnerships appear easy. John Krasinski and Emily Blunt, for example, have enjoyed « It » couple status since long before co-starring in Krasinski’s breakout directorial hit, A Quiet Place.
While some A-list couples are clearly a match made in heaven, others have left us dumbfounded, like the brief fling between Cher and Tom Cruise at the start of his career. Opening up to Oprah Winfrey on Oprah (via Daily Mail), the iconic singer admitted to dating the actor, 16 years her junior. « It could have been a great big romance because I was crazy for him. » If only she could turn back time!
If that piece of celebrity goss isn’t enough to leave your mouth agog, don’t worry, we have something even better for you. We’ve rounded up some bizarre and swift encounters that most of us blinked and missed while they were happening. From a disastrous sushi date between two ex-Disney stars to a certain legendary crooner who got the King of Pop tipsy, read on to discover some unlikely celeb couples who never made it past the first date.
This model reminded Drake not to ‘kiss and tell’
Canadian rapper Drake has certainly romanced a lot of famous ladies in his life. From wooing JLo with some decadent diamonds to publicly announcing his love for his rumored girlfriend at the time, Rihanna, at the 2016 VMAs, Drake is no stranger to Hollywood flings. But a surprising star to add to his roster of flames? Tyra Banks! Not the first time he’s been linked with a Victoria’s Secret beauty, the « In My Feelings » singer opened up to Ellen DeGeneres about his one date with the supermodel. « I went on a date with her one time, yeah. We went to Disneyland in disguise actually, which was fun. »
Audiences couldn’t believe it, and neither could Banks who happened to be watching the show. Soon after, she dished to Steve Harvey that Drake’s admission blew up her phone. « I’m watching Ellen and I’m like, ‘I can’t believe it.’ And then my phone is hitting up. And then social media, my Twitter, my Instagram … ‘Ohh, girl you went to Disneyland? What you wear?' » The model then proceeded to do a playful freestyle rap about the date and confirmed it — also proving that she definitely shouldn’t switch careers into the realm of hip-hop.
There’s nothing fishy going on between these stars
A Hollywood Casanova through and through, Shia LaBeouf has a tendency to romance his co-stars and then proceed to stay on good terms with them afterward. Dishing to a now-defunct Details (via Us Weekly) in 2011, LaBeouf confirmed an off-screen romance with his Transformers co-star, Megan Fox. « The time I spent with Megan was our own thing, and I think you can see the chemistry onscreen. » Years later, the raven-haired beauty would appear on an episode of Andy Cohen’s Watch What Happens Live, and confirm LaBeouf’s statement, proceeding to gush about her former flame, declaring she « loves him. »
It’s in that same Details interview that LaBeouf also spoke highly of his Wall Street: Money Never Sleeps co-star-turned-girlfriend Carey Mulligan, whom he parted ways with in 2010. « I still love her … I think she’s a f***ing awesome person and an incredible actress. We’re still pals. »
However, there’s one celeb who allegedly didn’t fall for his charm. After babbling praise about his exes, LaBeouf spilled that he went on one date with former Disney star, Hilary Duff. The Sydney Morning Herald revealed some additional dirt from the Details interview, including how he took the Lizzie McGuire star out on a sushi date. « (It was) probably the worst date either of us has ever had, » LaBeouf said. Yikes!
The King and Queen of Pop loosened up with wine
Michael Jackson and Madonna combined their legendary forces back in 1991 and graced the Oscars red carpet together — looking like decadent perfection. The pair appeared absolutely glamorous, with the King of Pop sporting a bedazzled tux, and the material girl looking like a ’90s Marilyn Monroe.
Fast-forward to 2016, when Madge finally set the record straight about that iconic night. During an episode of Carpool Karaoke with James Corden Madonna revealed that she did, in fact, smooch the pop star with « tongue and mouth kissing. » She went on to explain that she had to make the first move, as Jackson was « a little bit shy. » Not missing a beat, the « Like a Virgin » songstress went on, « he was a willing accomplice. I did get him to sort of loosen up with a glass of chardonnay. And it did wonders. »
The blonde beauty still remembers the date fondly, and as time has gone on, she reminisces about it more openly. In March 2018, Madonna posted a photo of that memorable evening to Instagram, captioning it, « Best date ever. »
This actress didn’t even get a kiss from Donald Trump
Candice Bergen has done some legendary things in her life. From being the first female to host Saturday Night Live to being so beautiful that Jane Fonda wanted to push her off a ladder, Bergen is iconic. She’s rubbed elbows with a lot of Hollywood’s finest throughout the years, but did you know she also went on a date with Donald Trump?
The actress and model shared this surprising secret on an episode of Andy Cohen’s Watch What Happens Live, where she admitted to going on a single date with Trump back in college. The star revealed that future president picked her up « wearing a three-piece burgundy suit and burgundy patent leather loafers and in a burgundy limousine. » As Cohen pried to find out if there was chemistry between the two, Bergen shot him down, explaining, « No, I was home very early. » Did she at least get a kiss? « There was no physical contact, whatsoever … he was a good looking guy and a douche. »
It’s certainly not the first time Bergen has been in presidential company, as the starlet has mingled with the Reagans, too!
‘Nobody nails down Nicholson’
Jack Nicholson is notorious for chasing Tinseltown tail. In fact, his tendency to play by his own rules has garnered so much attention, he’s even had a biography written about his eccentric way of living. Marc Eliot, the writer who penned the « unauthorized » account of the actor’s life, chatted with CNN, revealing even more juicy information. For example, it’s said that The Shining lead « may have bedded more women than any other star, » except for Warren Beatty — allegedly. From Melanie Griffith to Anjelica Huston, Nicholson has definitely been around.
What about an unlikely hook-up that nobody saw coming? Real Housewives of New York City star Sonja Morgan can add herself to Nicholson’s list. Certainly armed with her own black book of celebs, Morgan revealed her brief tryst with the Hollywood legend to Andy Cohen on Watch What Happens Live. Playing a game of « Would Morgan Date Him? » Cohen landed on Nicholson, causing the RHONY star to pause and say, « Have I?! » before proceeding to laugh. With the audience in an uproar, she high-fived Cohen, exclaimed, « He’s so much fun! » and described their time together as « one big sloppy mess, whatever… »
It turns out, they didn’t go past … whatever, with the reality TV star cooly stating, « Nobody nails down Nicholson. »
Cameron Diaz is Robbie’s angel
Happily married to his wife, Ayda Field, since 2010, Robbie Williams has one of his former flames to thank for their marital bliss! Per The Sun, Williams linked up with Cameron Diaz in 2003 when paps caught a glimpse of the pair out on a Santa Monica beach date, lip-locked and holding hands.
It turns out, the date didn’t snowball into a greater romance, but the two remained friends! So much so, in fact, that Diaz was there for Williams during a split from Field, offering up some relationship advice. The musician spoke to Lorraine Kelly on Lorraine to explain just how the Charlie’s Angels star saved his love life. « I split up with Ayda three times … I was out one evening and I was with … Drew Barrymore and Cameron Diaz, and I was talking about this girl I had just split up with. » He went on to reveal that Diaz opened his eyes by saying, « It sounds as though it’s not over, » giving Williams a moment of clarity to re-think his decision.
Nowadays, Field has definitely tamed the former womanizer. The star got real with The Sydney Morning Herald and explained how « unfazed » she is at Williams’ long list of conquests, which allegedly include Nicole Kidman, Rachel Hunter, and two Spice Girls. « Rob’s slept with lots of people, but it doesn’t bother me because what happens before you meet someone is part of their journey. »
Simon Cowell may be ‘too shy’ for a one-on-one date
Who would have thought that co-judges of Britain’s Got Talent, Simon Cowell and Amanda Holden, went on a date once? The duo, which we’re more used to seeing bicker on the show, actually had their very own rendezvous years ago — kind of. The blonde stunner dished exclusively to Heart that Cowell once took her out, and while he calls it a date, she « calls it dinner! » Holden then revealed that the notoriously tough judge is actually quite shy around women, so their dinner was really more of a group date. « I don’t think he’s ever been on a date where it’s just him and somebody else, because he’s actually quite shy and I don’t think he’s very good on a one to one. » Who would have thought?
Although Holden is happily married, as of this writing, and Cowell is with his long-term girlfriend, Lauren Silverman, Holden revealed that she « always loved » her fellow co-star. It’s no secret that the duo certainly has undeniable chemistry, but they pursued their other romances further before anything serious could happen between them. In fact, Holden believes Cowell’s blossoming romance with Silverman has made him « definitely [go] soft! »
Is Matthew McConaughey dazed and confused about this date?
Matthew McConaughey has had his share of famous flings. From Sandra Bullock to Penelope Cruz, the rom-com veteran sure knows how to woo! Preferring to keep things light-hearted, the Dazed and Confused star has nothing ill to say about his former flames. In an interview with Elle, McConaughey revealed he « doesn’t dislike » any of his exes. « If I took time to form a relationship, it’s gonna hurt when we move on, but are you puttin’ Wite-Out over all that beautiful time together? »
However, one celeb he did seemingly put Wite-Out over was Janet Jackson. After the duo had their photo taken together at the 2002 Grammys, Jackson actually admitted to Upscale Magazine (via The Telegraph) in 2006 that the two had a fling. « It was for a minute, that’s why I am so hesitant to mention it. » While the « Together Again » singer had no issues coming clean, McConaughey did. According to The Telegraph, shortly after their public appearance, the actor said, « We swapped some music and she’s a dear lady … but we’re not dating. » Hmm…
Fast forward to 2019 where the actor finally came clean on Andy Cohen’s Watch What Happens Live. When Cohen asked him about the 17-year-long dating rumor, McConaughey chuckled for a while, before finally revealing, « We went and had dinner one night. That was sorta it. »
Careful what you say about Colin Farrell!
He was the Irish bad boy riding the success of the Hollywood blockbuster Phone Booth, and she was one of the biggest pop stars of the time, so it’s no wonder the world went nuts when Colin Farrell and Britney Spears made their red carpet debut together in January of 2003. Attending the premiere of The Recruit, the duo had their photos taken as they walked hand in hand, and then continued their date into the wee hours afterward! As reported by USA Today (via People) at the time, Spears « met up with Farrell at the Chateau Marmont on Sunset Strip » where they proceeded to make out!
Months later, in July, the « Toxic » songstress admitted to W magazine (via People) that she locked lips with Farrell, but that nothing else came out of their fling. « Yes, I kissed him. … He’s the cutest, hottest thing in the world — wooh! … But it was nothing serious. »
We’re guessing that the Minority Report star must have gotten wind of Spears’ interview, as the tabloid The People (via PopDirt) reported that the prankster allegedly mailed the pop princess a T-shirt saying, « I slept with Colin Farrell and all I got was this lousy T-shirt! » As The Telegraph would later mention, the gag gift may or may not have happened — so take it with a hilarious grain of salt.
Shia LaBeouf and Rihanna unfortunately didn’t find love
Shia LaBeouf makes our list again with a pretty unlikely first date pairing. Tabs around the world couldn’t believe their eyes when the Transformers star was spotted out with Rihanna at the Kate Mantilini restaurant in Beverly Hills in 2007. The two were never seen together again, with the « Umbrella » crooner denying that they even went out on a romantic date. As she revealed to the press at a NASCAR event at the time (via PopSugar), « Me and Shia, we are just friends, you know, we barely even know each other. »
The entire affair remained pretty hush-hush until 2009, when LaBeouf had an interview with Playboy (via MTV) for the magazine’s June issue. The actor recalled that it was actually RiRi who reached out to him. « [I was] filming a sword fight when I got the message. I said, ‘Can this be my life?' » Although excited about the opportunity to date the Barbados-born beauty, the connection simply wasn’t there. « It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends. »
Joey Fatone asked for permission to take this pop star out
As rambunctious of an entertainer as Pink is, she certainly has a solid love life. Married to motocross pro Carey Hart since 2006, the « Beautiful Trauma » songstress was actually the one who proposed to her beau. Explaining in an interview with Supercross, Pink wrote « Will U Marry Me? » on a pit board during one of his races. Completely distracted, Hart said yes, to which the singer promptly responded with, « Well, get your a** back on the track. I don’t marry losers. »
Clearly someone who has a way of charming celeb hunks, Pink also revealed to Glamour in 2013 that she once dated a boy band member. When she opened up for *NSYNC back in the early 2000s, she actually went on a date with Joey Fatone. « Joey Fatone was in love with me, » Pink proclaimed, before adding, « He took me to Friendly’s on a date and he bought me an ice cream. Such a sweetheart. He asked my dad’s permission » We wish we had photos of such a cute encounter!
Drew Barrymore had ‘too many fish to fry’
There’s no denying that Christian Bale is popular with his female fans. It turns out, however, he may have more in common with Patrick Bateman, his American Psycho character, than one would think. Well, not the murder part, but bear with us. According to a chat the Daily Mail had with Bale’s former assistant, Harrison Chung, the actor « became his family’s main breadwinner » after his first major role as a teen, sparking the England-based brood to move to Hollywood. When his career really took off in 2000, Chung was witness to Bale’s father allegedly preparing his son breakfast every morning. He would bring it to him, yelling, « Who is the greatest actor in the world? » Bale would then yell back, « I am! I am! »
It’s no wonder then, that with his seemingly inflated ego, Bale would have some difficulty getting rejected. The British actor revealed to GQ Australia that he went on one date with Drew Barrymore when they were teens! « We went to see some bloody awful horror film, and that was the end of it. She never called again. »
Andy Cohen got wind of this fact and asked the actress about the date during an episode of Watch What Happens Live. Grilling her about how she could possibly reject Bale, the Never Been Kissed star explained, « I don’t know! I mean, he was so nice. … I wasn’t like super boy crazy. I had a lot of fish to fry. »