40 Surprising Romances Among Hollywood Celebrities

While we are used to unusual pairings onscreen, real-life lovebird combinations are very different from the movies. There are real-life Hollywood couples that we knew were good fits for each other. Then, there are the downright shocking ones. 

Let’s begin with one of the most shocking love stories in the celebrity arena—multiple award-winning rock star, Avril Lavigne and hip-hop heavyweight, Tyga. This one was shocking for two reasons

After two divorces and several other relationships spanning three decades, Madonna shocked the industry when her relationship with athlete Josh Popper became public. The seven-time Grammy award-winning songstress has not given up on love. 

In our opinion, Pete Davidson is one of the most charming celebrities around. The star-studded array of ladies who have been swayed by his personality is pretty enviable. From Kim Kardashian to Ariana Grande, Davidson has always had an eye for equally charming female compatriots.

In February 2023, Selena Gomez gave her fans one of the earliest surprises of the year when she was seen with Taggert several times in the span of a few weeks. These meetings included a rumored meeting at a bowling alley where they reportedly made out.

This love story revolves around the popular series Vanderpump Rules and allegedly involves the biggest cheating scandal in the history of reality television. In March, news broke that Tom Sandoval was cheating on his co-star and partner of nine years, Ariana Madix, with another co-star, Raquel Leviss. 

Even after releasing a track titled “Dua Lipa” which featured in his 2022 album, Come Home, the Kids Miss You, many fans failed to get the hint of an burgeoning love story between Jack Harlow and Albanian singer, Dua Lipa.

Canadian-born rap sensation Drake refers to lots of female celebrities in his tracks. So, his mention of Serena Williams in “Worst Behavior,” a 2013 track, didn’t spark much suspicion. 

Janet Jackson and Matthew McConaughey have both attended many industry-related events in the past, but rumor has it that they discovered their attraction to each other at the 44th Grammy Awards. 

Rumors about a romantic engagement between the pair gained some credibility after they were seen leaving the Golden Globe awards on January 6th, 2019. Pete is the third stand-up comedian on Kate’s list of romantic partners. 

After meeting on the set of the 2017 movie Changeland, the now grown-up child movie stars began to see a future with each other. After what looked like a soon-to-be short-lived relationship, the pair shocked everyone by having a child together. 

This exciting love story takes us all the way back to the 1980s. At the time, both celebs had already made a name and some significant fortunes for themselves. 

Not many people thought rapper 50 Cent and late-night show host and comedian Handler could find love in each other. But 50 Cent’s appearance on an episode of her show was enough to sway even the most pessimistic opinions. 

In February 2020, Kendall Jenner and Bad Bunny had dinner together and left the building separately. The exit strategy did not turn out to be very effective in dousing suspicions that would later be confirmed.

It was while Kardashian was working with Paris Hilton that she met Cannon, already a popular TV show host. The relationship became the talk of the town for a short while, and it lasted before it ended in 2007. 

Hollywood celebrity couples are known to meet at red-carpet events and birthday parties of colleagues. The relationship between Chelsea Peretti and Jordan Peele is an exception—they met on Twitter. 

Gwen Stefani and Blake Shelton were both hired as coaches on the seventh season of The Voice back in 2014. During their time working together, it is believed the seed of love was sown in the hearts of the pair, who were both married at the time. 

This pair fell in love after meeting on the set of the movie Don’t Worry Darling in September 2020. The next time they would be caught together was holding hands during a wedding in January 2021. 

When Kourtney Kardashian and Travis Barker made their relationship public, it sent shockwaves across their fan base. But they had known each other for quite a while before they got serious. 

During an appearance in Watch What Happens Live with Andy Cohen, Frankel finally admitted to dating Stonestreet. “I went out with him on two dates” were the only words she needed to mutter to end years of speculation. 

If the 32-year age difference doesn’t distract you, you will probably see that Taylor and Paulson are happy in each other’s arms. Adorable pictures of the couple holding hands got the internet buzzing. 

After Holmes ended her six-year marriage to Tom Cruise, it took about one year for her to find love again. This time, singer and actor Jamie Foxx was the lucky guy. 

Most of the time, our celebrity relationships begin on movie sets. When Megan Fox and Machine Gun Kelly met on the set of Midnight in the Switchgrass, Megan had been married to Brian Austin Green for ten years. 

It was in 1987 when Jason Mamoa first saw Lisa Bonet. She was on TV as part of the cast of The Cosby Show. Jason, who was only eight years old, had fallen in love. But it was not until two decades later that his wishes came true. 

It was Bow Wow who blew the lid on the secret relationship between Solange and Lil Wayne. During a clubhouse session, the Let Me Hold You crooner casually mentioned that Weezy had dated Solange, the younger sister of Beyonce. 

Even though they have now split, Rose’s involvement with Chmerkovskiy was one relationship no one saw coming. Given she had come out of relationships with Wiz Khalifa and Kanye West, fans were probably expecting another love story with a music industry great. 

This relationship went down as one of the most controversial of the decade. The twisted love affair story got the attention of fans with one casual admission—Alsina claimed during an interview that he had Will Smith’s blessings to date his wife, Jada. 

Contrary to Rihanna’s wishes, news that she was dating rapper Travis Scott broke out after Scott admitted to it in an interview with Complex editor Lawrence Schlossman. Scott had told Schlossman to keep it under wraps, but the later was too excited to keep it to himself. 

By the time Rodgers, the Green Bay Packers quarterback, called Woodley his fiancée at the NFL MVP acceptance speech, fans had already begun to notice the signs. The athlete would later confirm their engagement on Jimmy Fallon’s late-night talk show. 

It was while she was working as a waitress that Valladares met Efron. The charming actor sat in her section and got her number before leaving. 

Although they have been quite mum about how they got together, Munn and Mulaney are still going strong. This pair is surely one you wouldn’t expect.

We guess you can’t go wrong when it comes to a  “Milkshake. ”Bill Murray and the Milkshake” singer Kelis was reportedly an item for a hot second.

These actors despite a 21-year age gap and countries miles apart got together.  This daring Brit and this all-American funny guy went strong for about 3 years.

Jessie J and Channing Tatum come from completely different worlds. Channing, a dancer and actor of humble beginnings, and Jessie, a multitalented singer extraordinaire.

What is it about the funny guys? Do you think somehow they always get the girl because of a witty joke and a smile? This unlikely pairing between Julie Bowen and David Spade seems unlikely, but is it really?

The Game of Thrones star Sophie Turner is a serious actress with big films under her belt, like X-Men. While Joe Jonas, a boy bander with a former Disney show seemed like worlds apart. Although we didn’t see this love story unfolding it seems to work somehow.

Could you imagine if Iron Man and Carrie Bradshaw of New York dated? What a strange pair they would make, well you don’t have to venture too far off because the actors who played them got together.

Shaquille O’Neal and Nicole Alexander couldn’t be more opposite of a pairing. Even just looking at them, their high difference looks almost unreal.

Katharine McPhee and David Foster need to be on this list. With a 35 year age gap, it pushes the boundaries more than most.

David Cross and Amber Tamblyn sure are a quirky couple. This unexpected pair met by accident while getting on the same flight.