14 unlikely celebrity couples fans didn't see coming

  • Whether they don’t run in the same circle or have major age differences, some celebrity pairings come as a surprise.
  • Ariana Grande and Pete Davidson surprised fans with their brief romance as did the now-married Nick Jonas and Priyanka Chopra.
  • Fans may have forgotten that Evan Rachel Wood once dated Marilyn Manson and Drew Barrymore was married to Tom Green.

When it comes to celebrities, their personal lives often make as big a splash in tabloids, blog posts, and entertainment news pieces than their creative projects.

This rule becomes even truer when two surprising famous people start dating. Some celeb romances seem like unsurprising fits, while others, whether it’s because they didn’t appear to run in the same circle, have a dramatic age difference, or just seem to have entirely different personas, may inspire a few head tilts.

Here, we’re running through a list of 14 celeb pairings, both past and present, that came as a surprise.

In 1985, Cher met Tom Cruise at Madonna’s wedding to Sean Penn.

Shutterstock / FeatureFlashCher and Tom Cruise had a brief but ‘hot’ relationship.

Here’s a perfect storm of 80s nostalgia. At the 1985 wedding between Madonna and Sean Penn, Tom Cruise – a Hollywood “It Boy” thanks to his starring role in “Risky Business” – met Cher, already a literal living legend. This chance encounter led to a brief romance that Cher still remembers as particularly steamy. “It was pretty hot and heavy for a little minute,” Cher reminisced to Andy Cohen on a 2013 episode of “Watch What Happens Live.”

If not for the wedding, it’s hard to imagine the two would have met.

Billy Bob Thornton and Angelina Jolie were a major tabloid fixture during their brief marriage.

GettyAngelina Jolie and Billy Bob Thornton were married for three years.

Billy Bob Thornton met future wife Angelina Jolie on the set of “Pushing Tin” in the late 90s, right before Jolie hit the big time with her star turns in “Gia” and “Girl Interrupted.”

The pair fell into a courtship that can only be described as intense (like, wearing-vials-of-each-other’s-blood-around-their-necks intense). Thornton and Jolie married in 2000 and divorced in 2003, and Thornton told Vanity Fair in 2016 that they’re still “on good terms.”

Drew Barrymore and Tom Green were married in the early 2000s.

Brenda Chase/GettyImagesBarrymore and Green had a whirlwind marriage.

In 2000, America’s sweetheart Drew Barrymore surprised her fans by dating goofy comedian Tom Green.

The two nearly tied the knot in front of “Saturday Night Live” cameras while Green hosted an episode, but Barrymore backed out at the last minute. They actually married in 2001, but Green filed for divorce just a few months later, citing “irreconcilable differences,” according to wire service reports from Entertainment Weekly.

Long before he married Blake Lively, Ryan Reynolds was engaged to Alanis Morissette.

Donald Weber/Getty ImagesReynolds and Morissette were almost married.

These days, it’s hard to think of Ryan Reynolds without his current wife, Blake Lively, immediately coming to mind. But before he married the once and future Serena van der Woodsen, Reynolds popped the question to another major star, Alanis Morissette.

The pairing surprised fans as Reynolds at the time was known primarily for his semi-ridiculous role in “Van Wilder” while Morisette was a 90s angst-rock icon.

The two first became an item in 2002, Reynolds proposed in 2004, and they parted ways in 2007.

Evan Rachel Wood fell for Marilyn Manson because of the “freedom” he promised her.

Scott Wintrow/Getty ImagesWood said she found ‘no judgments’ in Manson.

In 2006, when she was 18 years old, Evan Rachel Wood – then best-known for “Thirteen” and “Once and Again”- met goth rocker Marilyn Manson at the Chateau Marmont in Hollywood.

Although Manson was 18 years her senior, she felt an immediate connection to the shocking singer, telling Rolling Stone in a 2016 interview that, in Manson, she “met somebody that promised freedom and expression and no judgments.” The two became engaged in 2010 and split in 2011, and Wood went on to marry actor Jamie Bell and have a son with him before their 2014 divorce.

Amber Tamblyn and David Cross first felt sparks while making fun of the SkyMall catalogue on a flight.

“Travelling Pants” star Amber Tamblyn felt drawn to her now-husband, “Arrested Development” funnyman David Cross, aboard an aeroplane.

In 2012, Tamblyn and Cross told current HQ Trivia host Scott Rogowsky (then the host of his own live show “Running Late with Scott Rogowsky“) that they spotted each other on a plane heading from Houston to Louisiana, asked to have their seats reassigned so that they could sit side-by-side, then spent the flight chatting and making fun of the SkyMall catalogue’s offerings.

In spite of their sizable 19 year age difference, they have been together ever since.

Samira Wiley fell for “Orange is the New Black” writer Lauren Morelli on-set.

Frazer Harrison/Getty ImagesSamira Wiley and Lauren Morelli married in 2017.

When “Orange is the New Black” star Samira Wiley met show writer Lauren Morelli, Morelli was already married to her then-husband.

Even so, she and Wiley clicked right away, and after spending plenty of time together on-set and over the phone when their shooting schedules conflicted, their friendship developed into a burgeoning romance.

The relationship surprised both fans and Morelli herself, who only started to self-identify as a lesbian after beginning her work on “OITNB” in 2012. The couple married in Palm Springs in 2017.

About the romance, Wiley told Bust magazine, “The deep intimacy of being two people talking about the core of who we are. Talking about our journeys. Not even necessarily flirting on set, but on the phone, thousands of miles apart, talking about Who are we? And does this make me a different person? Does this actually make me who I am now? That’s how we fell in love.”

Benji Madden’s brother Joel first introduced him to now-wife Cameron Diaz.

Benji Madden/InstagramMadden and Diaz were married in 2015.

Although Cameron Diaz had numerous mutual friends with Good Charlotte rocker Benji Madden (including Madden’s brother Joel and his wife Nicole Richie), she didn’t officially meet her future spouse until she decided to throw a 2014 dinner party at her house.

She invited Joel and Nicole, Joel asked if he could bring his brother along … and the rest is history for this seemingly-random couple.

Even Diaz admitted they weren’t exactly in the same circle.

Appearing on Andy Cohen’s radio show, Diaz said “The first thing I said when I first met my [would be] husband was, ‘He’s hot.’ How come I didn’t know this before? We had never been in the same circle.”

In a total departure from her super-public marriage to Tom Cruise, Katie Holmes opted to keep her reported relationship with Jamie Foxx low-key.

Getty/Alberto E. Rodriguez/Jamie McCarthyFoxx and Holmes keep their reported relationship out of the spotlight.

If you happened to turn on a TV at any point during 2005, you’re well aware of the super-hyped phenomenon that was the Katie Holmes-Tom Cruise relationship. From Tom jumping on Oprah’s couch to their wedding to the birth of baby Suri to rumours about their split, that entire romance happened in a spotlight.

But Holmes kept her next relationship rather quiet. Although both parties have spent years dodging questions about their dating status, Katie Holmes and Jamie Foxx (who actually met when Tom Cruise co-starred with Foxx in “Collateral”), it’s reported that these two have been an item since at least 2015.

The union of Gwen Stefani and Blake Shelton represents an interesting collision of alt-rock and country-pop.

Kevin Winter/Getty ImagesShelton and Stefani met on ‘The Voice.’

One of the most highly-publicized “showmances” in recent memory, the three-year relationship (beginning in 2015) between “The Voice” judges Gwen Stefani and Blake Shelton surprised onlookers due to the differences in their public images.

Stefani’s best known as the quirky, fashion-forward frontwoman of the 90s alternative hitmakers No Doubt, while Shelton’s a classic country “good ol’ boy” with a pop twist.

Further, when the two first met, Shelton was married to fellow country star Miranda Lambert.

Read more: Gwen Stefani and Blake Shelton just released a romantic music video together – here’s a timeline of their love story

Many onlookers find the age difference between Holland Taylor and Sarah Paulson surprising.

Nicholas Hunt/Getty ImagesSarah Paulson and Holland Taylor have a 32-year age gap.

While significant age differences between romantic partners are hardly a novel concept in Hollywood, the 32-year gap between “Legally Blonde”‘s Holland Taylor and her girlfriend, “American Horror Story”‘s Sarah Paulson, definitely made some waves when they announced their relationship in 2015.

Nevertheless, Paulson feels completely confident about her and Taylor’s choice to be together, telling Elle that “I didn’t choose to fall in love with the person I fell in love with. But I think why it’s interesting to people is that on paper, it’s unconventional. For a person who might find themselves in a situation that they fear will be misperceived or judged, maybe they could see me living my life in a way that is authentic to me-just trying to be as real as possible. If that inspires anybody else, that can’t be a bad thing.”

Short-lived though it was, the whirlwind romance between Ariana Grande and Pete Davidson made a massive impact on the celebrity-news landscape of 2018.

Jamie McCarthy/Getty ImagesDavidson and Grande had a highly-publicized relationship.

After hosting an episode of “Saturday Night Live” in 2016, songstress Ariana Grande said she developed a crush on Pete Davidson.

In May 2018, the two officially became a couple, and one month later, Grande started publicly wearing the engagement ring purchased for her by Davidson.

But in October, the two announced their breakup. The speed of the relationship surprised celeb watchers and inspired plenty of think pieces (and, of course, “SNL” sound bytes) … but we did get “thank u, next” out of the whole thing, so it’s really a win for everyone.

Read more: Ariana Grande says she’s ‘thankful’ for Pete Davidson in a new song about her exes – here’s a complete timeline of their relationship

The marriage of Bollywood superstar Priyanka Chopra and former boy-bander Nick Jonas astonished audiences around the world.

A massive movie star in her home country of India (with a rising professional profile stateside, thanks to projects like “Quantico” and “Isn’t It Romantic”), Priyanka Chopra has long topped international lists of top celebrities. So when she started dating Nick Jonas, a former pop star 10 years her junior who’s best known for the eponymous boy band he started with his brothers, many fans of both Chopra and Jonas had trouble understanding the connection between the two.

In spite of the fan confusion, Chopra and Jonas tied the knot in 2018.

Read more: Here’s a complete timeline of Nick Jonas and Priyanka Chopra’s relationship, who recently tied the knot at an Indian palace

Tesla founder Elon Musk and musician Grimes regularly send mixed messages about their relationship status.

Neilson Barnard/Getty ImagesElon Musk and Grimes at the Met Gala 2018.

Tech mogul Elon Musk frequently pairs up with actresses, models, and musicians, so his choice to start dating Canadian singer Grimes wasn’t too surprising in and of itself, although her nouveau-goth look felt like a sharp departure from past Musk partners like Amber Heard and Talulah Riley.

But the way the two documented their relationship on social media inspired countless “are they together or not?” questions throughout 2018. From Musk abruptly unfollowing Grimes on all social platforms in September to photos of the two visiting a pumpkin patch in October appearing on innumerable gossip blogs, this pair kept the public guessing.

Read more: Elon Musk and Grimes stopped following each other on social media – here’s a look back on their relationship

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