38 Celebrity Couples You Won’t Believe Were Once Together

Does anyone else remember when the Counting Crows rockstar dated Jen? They were together back in 1995, and Duritz hilariously admitted he didn't know who she was when they first got together: "I honestly had no idea who she was. I had been on the road during all of Friends. I had never seen it, I don't think."

Singer Britney Spears and notorious Hollywood bad boy Colin Farrell made waves when they attended the premiere of Farrell’s film The Recruit together in 2003. While these two seemed smitten on the red carpet – and were rumoured to have been spotted hooking up that night – the pair were coy about admitting to anything official. This maybe-coupling seemed to fizzle out fast.

In a 2016 bit with James Cordon for Carpool Karaoke, Madonna admitted to hooking up with the kind of pop, Michael Jackson, noting, “he was a little shy.” From unusual celebrity couplings to unusual celebrity fashion — these are the trends that left us scratching our heads!

Glee star Naya Rivera found out she was no longer getting married from the internet after Big Sean opted out of it all and posted his decision online. The actress/singer wrote all about it in her tell-all book Sorry Not Sorry.

That's right, before Ariana Grande, Big Sean and Naya were not just a thing — they were engaged.

Never forget: "You Oughta Know" that Canadian singer Alanis Morissette and Full House's (uncle Joey!) Dave Coulier were an item once upon a time. In fact, actor-comedian Coulier has admitted the classic 90's alternative rock song was, indeed, about him. And one time, Full House star Bob Sagat said in an interview that he was there when Morissette called during dinner (you know the line of the song!) — but with Sagat, it's always hard to say whether not it's just jokes.

But this was all long ago and now Morissette is married — and busy being slammed for her parenting these days.

Fans of the hit TV show Gilmore Girls may not be surprised to discover that the chemistry between characters Rory (play by Alexis Bledel) and Jess (Milo Ventimiglia) was the real deal on — and off — screen. The pair dated for three years soon after meeting on the set of the show.

Reality TV star and social media force Kim Kardashian dated Nick Cannon in 2006. Apparently it was Kim’s sex tape with Ray-J that was the nail in the coffin on their brief romance.

From big hookups to major breakups, celebrities do everything on a bigger scale — just check out the outrageous gifts these stars have gifted each other.

With nothing but kind words to say about one another, it was David Arquette who first revealed that he and Drew Barrymore were once an item. If you’re scanning your brain to recall any movie chemistry between these two from their roles in Never Been Kissed, we should remind you — they played siblings!

As it turned out, 1998 was a good year for Ashton Kutcher. He'd just scored the role of his career as Kelso in That '70s Show and had up-and-coming actress January Jones on his arm. Unfortunately, these two would ultimately clash and, after a few short years, would move on from each other.

In a 1995 cover story for People, Courteney Cox was quoted as saying (of her relationship with Michael Keaton), “It’s the most important relationship I’ve ever had and he is the most wonderful person I’ve ever met.” At the time, the couple of more than five years had only parted a few months earlier; and based on the interview with People, there was anything but bad blood between them.

Before there was Heidi, it seemed Seal had eyes for another supermodel off the runway — Tyra Banks. The two dated in 1996, keeping a low profile during their brief fling.

After co-starring in the 1998 film, The Object of My Affection, there was obviously a little chemistry leftover between on-screen couple Jennifer Aniston and Paul Rudd. The pair dated briefly and were reunited on-screen in 2002, when Rudd took on the role of Mike Hannigan (Phoebe's beau!) on Friends.

Speaking of everyone’s favourite show to binge-watch on Netflix, check out character Rachel Green’s greatest style moments from the series.

Nominated for Best Supporting Actress for her role in Steel Magnolias, Julia Roberts looked every bit the Hollywood A-lister as she walked the red carpet with Canadian actor Kiefer Sutherland on her arm. The pair were heavy into the drama from the start, as Kiefer left his then-wife for Roberts after the pair met on set of Flatliners in 1990. The lovebirds quickly got engaged, but just days before walking down the aisle, Roberts dumped Sutherland over rumors of him cheating with a stripper. Soon after, she dated Kiefer’s good friend (and The Lost Boys co-star), Jason Patric. Talk about a whirlwind romance – and breakup!

Check out some celebrity family ties with our list of stars you didn't know come from famous families.

Before the Cruiser jumped on Oprah's couch to profess his love for Katie Holmes, he dated Cher in the 1980s. Even back then, it seemed like a crazy match, but it's nice to see they're still friendly.

Tom Cruise and Cher may not have made it as a couple, but check out our list of celebrity couples out to prove that true love in Hollywood can stand the test of time.

These days, everyone knows Ellen as the lesbian — but before Portia de Rossi, Ellen was in a super serious lady loving celebrity relationship with actress Anne Heche from 1997 to 2000.

Their break up was big news back then — it capped off a very publicized romance between the two. And Ellen had to deal with the real-life lesbian nightmare of Heche marrying a camera man from her stand-up comedy tour 13-months after their split (and having his baby the following year). The Anne and Ellen relationship was a thing back in the day.

Funnyman Owen Wilson and singer Sheryl Crow were linked from 1999 to 2001. Since then, Crow hasn’t been shy in opening up about her struggles in past relationships – particularly those with other celebrities, noting in an interview with Good Housekeeping, “…what ends up happening is that one of you becomes smaller — and it was always me.”

OK, so these two were never “Instagram official” and it may just have been a quick bit of puppy love between the two former Disney stars, but this pair had a moment. No worries, Priyanka – these two are definitely old news.

Flash-forward to 2018 and Nick Jonas' newlywed bliss with  wife Priyanka Chopra.

These two famously made a (drunken) scene when they attended a basketball game together in New York in 2014. Their romance lasted about six months, after which the two allegedly had a (very) messy breakup. But could anything really have been messier than these two on a bender courtside?

These two had a brief romance in 1994, soon calling it quits, but reuniting professionally on the set of the 1998 film, Fear and Loathing in Las Vegas.

The two met on the set of the 2002 movie Murder by Numbers and dated for a few months. In 2011, Gosling recalled his time with Bullock — and his other famous ex, Rachel McAdams — fondly. "I had two of the greatest girlfriends of all time. I haven't met anybody who could top them." Don't worry, Eva Mendes, this was before your time.

Remember when these two dated for three years? They met on the set of The People vs. Larry Flynt and were even reported to be engaged. They didn't part on good terms, however. She even called him out on Twitter, claiming he still owes her $300,ooo.

Applegate was a big star on Married With Children; Pitt had a bit part on Knots Landing. They dated for a bit before she took him to the 1989 MTV Movie Awards where she dumped him and left with someone else. I think it's safe to say he recovered.

We thought Shia dating Hilary Duff was weird, but then we remembered Lizzie McGuire and Even Stevens and realized they were bound to go on a date at some point. LaBeouf revealed that he and Rihanna hooked up in 2007 for one date but admitted that "the spark wasn't there." He claims they're still friends, but even that seems... odd.

The Oscar winner dated the New Kids On The Block member. Yes, really.

The Ally McBeal co-stars began dating after he appeared on the show. They didn't last long, which worked out just fine, as he is now married to producer Susan Levin and she's with longtime beau Harrison Ford.

Alright, alright, alright. Ms. Jackson and Matty reportedly dated in 2002, after hitting it off at the Grammy's. They didn't last long, but Janet 'fessed up to the fling before she hooked up with Jermaine Dupri.

In 2001, before Wilson hit it big with Angels in America, he dated J-Love for about a year.

Before meeting longtime love Naomi Watts, the Ray Donovan star dated Sex and the City actress Kristin Davis in 2003.

She may be married to choreographer Benjamin Millepied with two kids, but before her happy family, she dated Moby. Of their short-lived romance, he said, "As far as the very brief affair that I had with Natalie, it's made me a target of a lot of nerd wrath. You don't date Luke Skywalker's mom and not have them hate your guts." Ha!

The two had been dating for a couple of months, but things cooled rather quickly upon Lovato learning Phillippe was going to be a dad again (with ex-girlfriend Alexis Knapp). Lovato was only 18 at the time, so a divorced dad of three who was twice her age probably wasn't Mr. Right.

The summer 2013 fling between the Man of Steel star and The Big Bang Theory actress came out of nowhere. Really, it was like someone picked their names out of a hat. The two were pap'd hard for a few days, but no one was buying their sudden, PR-friendly coupling and they were done 10 days after the first pics of them surfaced.

The two began dating in May 2008 and got serious — fast. Too fast for Armstrong, apparently, and he broke it off with the "needy" actress three months later. Ouch.

The actress and Witches of East End producer was briefly linked to the former 'N Sync star. She's even reportedly inspired some of his solo love songs.

Too bad, so sad – these are the shortest celebrity marriages.

Before fiancée Alanis Morissette and wives Scarlett Johansson and Blake Lively (to whom he is still married), Reynolds dated the 3rd Rock from the Sun alum for a year. Ryan is also one of the wealthiest Canadian actors.

The 2011 fling between Lively and DiCaprio was gossipy goodness. The two never officially went public, but they vacationed in Italy and the French Riviera and had a together blast in Disneyland. But it was all part of Lively's game. Blake may have spent that summer with Leo, but she was just waiting to pounce on her true end game, now-husband Ryan Reynolds.

The two dated in 2003, but the singer reportedly broke up with the Sports Night star a mere two months later, because she sensed that he wasn't "The One."

Before Mad Men, the actress dated the celebrated crooner and Rising Star host for three years before calling it quits in 2006.

The two dated after he appeared on her former late-night show. He even appeared on the Chelsea Lately finale where she asked him, "Seriously, are you over me?" Please. These two are totally going to hook up again — if they haven't already.