Can You Name These Cringey Celeb Couples?

By: Alex Wittman
Estimated Completion Time
7 min
Can You Name These Cringey Celeb Couples?
Image: KNBC

About This Quiz

Tbh, we can't think of a better way to escape work (or school or whatever other boring thing you're doing rn) than a little trip down memory lane. For real, we're turning back the clock and examining some of Hollywood's most random couples. Seriously, you're not going to believe some of these people actually dated.

Everyone has embarrassing exes (ourselves included), but when you're famous all those relationships, you'd rather forget live on thanks to the paparazzi. Can you imagine if the paps were there to snap pics of all your bizarre Tinder dates?! OMG, when those pics of Miley Cyrus and Kaitlynn Carter dropped, we'd never been so glad NOT to be famous. Poor Liam.

If you can't go through the grocery store checkout line without picking up a copy of People and low-key have the Daily Mail bookmarked so you can check it on the reg, then we think you might have what it takes to name all these cringey celeb couples.

Who did Madonna only recently confirm that she dated in the early '90s? Can you name the dude Mila Kunis was in love with pre-Ashton? How about the woman who was with Ashton pre-Mila? Wait, what couple started dating after meeting on the set of Vanilla Sky?! 

Take our quiz to see how many of these cringey celeb couples you can name!

Jennifer Lopez and Ben Affleck These two had the GOAT couple nickname. Can you name this cringey celeb couple?
Kim Basinger and Alec Baldwin
Jennifer Lopez and Ben Affleck
No cap, we are still living for the celebrity couple name "Bennifer." Even though it technically still worked when he dated Jennifer Garner, it just wasn't the same as when Ben Affleck and Jennifer Lopez were a thing.
Kate Moss and Johnny Depp
Gwyneth Paltrow and Brad Pitt

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Kristen Stewart and Robert Pattinson Teenage vampires, YKTV. Can you name this cringey celeb couple?
Kristen Stewart and Robert Pattinson
Omfg, do you remember the "Twilight" frenzy? What a time to be alive! Even more than Bella and Edward, fans were obsessed with Kirsten Stewart and Robert Pattinson. The pair called it quits for good in 2012 after the paparazzi snapped a pic of K-Stew canoodling with another dude.
Luke Wilson and Gwyneth Paltrow
Madonna and Michael Jackson
Miley Cyrus and Nick Jones

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Brad Pitt and Angelina Jolie People this beautiful should legally not be allowed to date. Do you remember this odd-AF celebrity couple?
Tyra Banks and Drake
Brooke Shields and Nicolas Cage
Brad Pitt and Angelina Jolie
Everyone thought Brad Pitt and Jennifer Aniston were so in love, but then he left her for Angelina Jolie. The two met while making "Mr. & Mrs. Smith," and their chemistry was fire. But it didn't last. They split in 2016.
Jared Leto and Cameron Diaz

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Lady Gaga Couple This star was born, but then it went supernova. Who are the people in this bizzare celeb couple?
Aaliyah and Jay Z
Ashley Olsen and Lance Armstrong
Britney Spears and Colin Farrell
Lady Gaga and Christian Carino
Not even a $400,000 engagement ring could make Lady Gaga stay with Christian Carino. While everything was going great with "A Star Is Born," Gaga's love life was falling apart. The couple broke up just before Valentine's Day.

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Taylor Swift and Tom Hiddleston Oh, you know she's gonna write a song about this. Can you name this cringey celeb couple?
Taylor Swift and Tom Hiddleston
No cap, Taylor Swift could appear in this quiz as many times as Tom Cruise (maybe more). But this time, we're talking about her relationship with Tom Hiddleston. The two dated following Swift's 15-month relationship with DJ Calvin Harris. Fans think the song "Getaway Car" is about Taylor dumping Calvin for Tom. Savage.
Amanda Seyfried and Justin Long
Kaley Cuoco and Ryan Sweeting
Megan Fox and Brian Austin Green

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Shia LaBeouf and Hilary Duff Major Disney vibes, tho. Can you name this cringey celeb couple?
Mel Gibson and Oksana Grigorieva
Shia LaBeouf and Hilary Duff
Wow, our Disney-loving hearts wanted this to happen, but Shia LaBeouf and Hilary Duff's romance was short-lived. Apparently, they only went on one date and, according to Shia, it was "the worst date either of us ever had."
Renee Zellweger and Kenny Chesney
Madonna and Sean Penn

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Jennifer Aniston and Vince Vaughn We love them as individuals but together is another story. Can you name this cringey celeb couple?
Justin Timberlake and Fergie
Jennifer Aniston and Vince Vaughn
Making a movie together called "The Break Up" didn't bode well for the future of Jennifer Aniston and Vince Vaughan's relationship. They only dated for a couple of months before deciding to go their separate ways.
Joaquin Phoenix and Liv Tyler
Matt Damon and Winona Ryder

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Katy Perry and Russell Brand OMG, we almost forget this was a thing. Who are the famous faces in this cringey celeb couple?
Katy Perry and Russell Brand
While many of our cringey celebrity couples just dated, Katy Perry and Russell Brand were actually married. The two tied the knot in 2010 but ultimately called it quits in 2012. Wait, where is Russell these days?
Nicole Kidman and Tom Cruise
Courtney Love and Kurt Cobain
Iman and David Bowie

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Jennifer Lopez and P. Diddy Yuh, she's on this quiz a couple times but with different dudes. Who are the famous faces in this cringey celeb couple?
Jennifer Lopez and P. Diddy
It's been so long since Jennifer Lopez and P.Diddy dated that he's since changed his name. Yeah, back then, he was known as Puff Daddy. The couple dated from 1999 to 2001. Wow, it doesn't look like J-Lo has aged a day!
Gigi Hadid and Zayn Malik
Usher and Grace Miguel
Jennifer Aniston and Justin Theroux

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Michael Cera and Aubrey Plaza This was a match made in awkward-AF heaven. Can you name this cringey celeb couple?
Demi Moore and Bruce Willis
Lenny Kravitz and Lisa Bonet
Michael Cera and Aubrey Plaza
Wow, the awkwardness is palpable. Like, you could cut it with a knife. After meeting on the set of "Scott Pilgrim Vs. The World," Michael Cera and Aubrey Plaza dated for a year and a half. In fact, they almost eloped in Las Vegas!
Johnny Depp and Winona Ryder

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Kim Kardashian and Kris Humphries This has to be one of the shortest marriages in the history of Hollywood. Can you name this cringey celeb couple?
Charlize Theron and Sean Penn
Kim Kardashian and Kris Humphries
Kim Kardashian and NBA player Kris Humphries had a whirlwind 90-day engagement before tying the knot in an extra-AF wedding ceremony in California. But if you thought their engagement was short, wait till you hear how long their actual marriage lasted: 72 days.
Miranda Lambert and Blake Shelton
Gwen Stefani and Gavin Rossdale

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Kylie Jenner and Jaden Smith Awww, young love (barf). Can you name this cringey celeb couple?
Tom Cruise and Katie Holmes
Ellen DeGeneres and Portia de Rossi
Kylie Jenner and Jaden Smith
Years before she became Stormi's mommy, Kylie Jenner dated Jaden Smith. The young couple was so serious that Jaden was even Kylie's date to Kim and Kanye's wedding in Florence.
Kristen Stewart and Robert Pattinson

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Emily Blunt and Michael Bublé Wait, these two were sort of adorable (just sort of, though). Can you name this cringey celeb couple?
Jennifer Aniston and Brad Pitt
Emily Blunt and Michael Bublé
OMG, how epic would it have been if Emily Blunt broke her silence in "A Quiet Place" with a Michael Bublé song?! The two were super private about their relationship, which took place between 2005 and 2008.
Britney Spears and Justin Timberlake
Jay-Z and Beyoncé

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Jessica Biel and Chris Evans Lol, she definitely has a type. What are the names of this cringey celeb couple?
Jessica Biel and Chris Evans
Okay, we can kind of see a resemblance between Chris Evans and Jessica Biel's now-hubby Justin Timberlake. Just us? Whatever. But yeah, Chris and Jessica were in an on-again-off-again relationship from 2001 to 2006.
Selena Gomez and Justin Bieber
George Clooney and Amal Alamuddin
Blake Shelton and Gwen Stefani

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Ariana Grande and Pete Davidson Tbh, we still can't believe this happened. Can you name this cringey celeb couple?
Drew Barrymore and Christian Bale
Justin Timberlake and Fergie
Ariana Grande and Pete Davidson
TBH, this has to be one of the strangest relationships Hollywood has ever seen, and that's saying a lot. Ariana Grande and Pete Davidson got engaged pretty much right after they started dating but split up five months later.
Pink and Joey Fatone

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Mila Kunis and Macaulay Culkin This couple low-key dated forever. Can you name this weird celeb couple?
Adele and Simon Konecki
Lady Gaga and Christian Carino
Mila Kunis and Macaulay Culkin
Before Mila Kunis married fellow "That 70s Show" actor Ashton Kutcher, she was in a long-term relationship with Macaulay Culkin. Yeah, that kid from "Home Alone!" The two were together for eight years.
Brie Larson and Alex Greenwald

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Britney Spears and Justin Timberlake We knew this was too good to last. What are the names of this cringey-AF celeb couple?
Ryan Phillippe and Demi Lovato
Lance Armstrong and Kate Hudson
JC Chasez and Eva Longoria
Britney Spears and Justin Timberlake
Pop sensations Britney Spears and Justin Timberlake seemed like they were destined to be together. But those all-denim red-carpet lewks were the beginning of the end. Britney ended up breaking Justin's heart.

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Jennifer Aniston and Paul Rudd Wait, they're kinda cute. What are the names of this celeb couple?
Jennifer Aniston and Paul Rudd
This one-time couple might be cringey, but can we all agree that Jennifer Aniston and Paul Rudd look like they haven't aged a day since they dated in the late '90s?! The pair starred in "The Object of My Affection."
Katie Couric and Bob Saget
Tom Holland and Zendaya
Stella Maxwell and Kristen Stewart

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Ciara and Bow Wow Not even making music together could save this relationship. Can you name this cringey celeb couple?
Lena Dunham and Jack Antonoff
Ciara and Bow Wow
Tbh, we're pretty much always bumping those mid-2000s bops on Spotify. But even so, we nearly forgot Bow Wow and Ciara were a couple back in 2006. They were together for two years, got engaged and even released a song together!
Fergie and Josh Duhamel
Chris Pratt and Anna Faris

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Cameron Diaz and Justin Timberlake These two could have totally worked out. Who are the people in this bizzare celeb couple?
Nick Lachey and Jessica Simpson
Brad Pitt and Angelina Jolie
Jennifer Aniston and Vince Vaughan
Cameron Diaz and Justin Timberlake
When we remembered Justin Timberlake and Cameron Diaz used to be a couple, we had to go back and watch "Bad Teacher." They two starred in the hilarious movie while they were dating.

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Keira Knightley and Jamie Dornan We hardly recognize the dude without his whips and chains. Can you name this cringey celeb couple?
Ryan O'Neal and Farrah Fawcett
Keira Knightley and Jamie Dornan
Jamie Dornan (or should we call him "Christian Grey") and Keira Knightly dated in the early 2000s. In those days, pretty much no one knew his name. Huh, we wonder what Keira thought of "Fifty Shades of Grey."
Carrie Fisher and Paul Simon
Sarah Jessica Parker and Robert Downey Jr.

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Gwyneth Paltrow and Brad Pitt No cap, these two look like they could be brother and sister. Do you remember this odd-AF celebrity couple?
Michelle Rodriguez and Cara Delevingne
Tom Cruise and Cher
Gwyneth Paltrow and Brad Pitt
"WHAT'S IN THE BOX?!" Ah, we had so many nightmares after "Se7en," which just so happens to be the movie that brought Gwenyth Paltrow and Brad Pitt together. They called it quits in 1997.
Edward Norton and Courtney Love

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Demi Moore and Ashton Kutcher People freaked over this age difference. Do you remember this odd celebrity couple?
Zooey Deschanel and Jacob Pechenik
Demi Moore and Ashton Kutcher
When Demi Moore and Ashton Kutcher tied the knot in 2005, she was 15 years older than him. The two split in 2013, and the rumors swirled that he cheated on her. Yikes! Hopefully, things are different with Mila.
Billie Lourd and Taylor Lautner
Nicki Minaj and Meek Mill

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Matthew McConaughey and Janet Jackson It doesn't get more random than this. What are the names of this cringey celeb couple?
Bradley Cooper and Irina Shayk
Kendall Jenner and Ben Simmons
Kate Beckinsale and Pete Davidson
Matthew McConaughey and Janet Jackson
This random-AF celebrity couple sent our heads spinning. Pop icon Janet Jackson and flannel-shirt-wearing Matthew McConaughey dated for, like, two seconds back in 2002. It was short-lived, but it definitely still happened.

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Tom Cruise and Penélope Cruz Same name, different spellings. Can you name this cringey celeb couple?
Katie Holmes and Jamie Foxx
Tom Cruise and Penélope Cruz
Before he ever jumped up and down on Oprah's couch, Tom Cruise dated Penélope Cruz for three years in the early 2000s. The couple met on the set of "Vanilla Sky." Even though Tom is, well, Tom, there's no doubt they were a fire couple.
Miley Cyrus and Liam Hemsworth
Lili Reinhart and Cole Sprouse

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Kim Kardashian and Nick Cannon Ah, we can't stop laughing. Do you remember this weird (that's an understatement) celeb couple?
Victoria Adams and David Beckham
Will Smith and Jada Pinkett
Reese Witherspoon and Ryan Phillippe
Kim Kardashian and Nick Cannon
Tbh, Kim Kardashian has, like, A LOT of cringe-worthy relationships. Nick Cannon is just the tip of the iceberg. The two dated in 2006 (you know, before Kim knew how to do her makeup and stuff).

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Sarah Jessica Parker and Robert Downey Jr Young Iron Man in love. Can you name this cringey celeb couple?
Sarah Jessica Parker and Robert Downey Jr.
In the late '80s and early '90s, Sarah Jessica Parker and Robert Downey Jr. were Hollywood's young "it" couple. Kind of crazy to think about now, but these two dated for seven years. Say what?
Johnny Depp and Amber Heard
Jennifer Garner and Ben Affleck
Kim Kardashian and Kris Humphries

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Nick Lachey and Jessica Simpson As long as we live, we will never forget their TV show. Can you name this cringey celeb couple?
Nick Lachey and Jessica Simpson
It's hard to fathom, but there was actually a time before everyone had a reality TV show. Nick Lachey and Jessica Simpson had one of the first with "Newlyweds." Hmm, maybe the pressure of filming every moment contributed to their divorce in 2006.
Kristen Johnson and Ryan Reynolds
Leonardo DiCaprio and Blake Lively
Sandra Bullock and Matthew McConaughey

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Justin Bieber and Selena Gomez We want these two to make one more song together, plz. What are the names of this cringey-AF celeb couple?
Natalie Portman and Jake Gyllenhaal
Kate Hudson and Alex Rodriguez
Selena Gomez and Justin Bieber
This relationship was all the on-again-off-again drama we could handle. Selena Gomez and Justin Bieber went back and forth for YEARS right up until he married Hailey Baldwin in 2018. So, it's def "off" rn, yes?
Angelina Jolie and Billy Bob Thornton

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Johnny Depp and Winona Ryder Since this relationship ended, we haven't seen stranger things (get it?). Can you name this cringey celeb couple?
Kiefer Sutherland and Julia Roberts
Owen Wilson and Sheryl Crow
Selena Gomez and Nick Jonas
Johnny Depp and Winona Ryder
Johnny Depp and Winona Ryder seemed perfect for one another when they started dating in 1989 after meeting on the red carpet. They were engaged for three years, and in that time, they starred in "Edward Scissorhands" together.

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Nicole Kidman and Tom Cruise Not him again. What are the names of this cringey-AF celeb couple?
Nick Jonas and Olivia Culpo
Emma Roberts and Evan Peters
Nicole Kidman and Tom Cruise
Tbh, we kind of cringe at any relationship that involves Tom Cruise. While he and Nicole Kidman were together, the couple had two children. Since ending her relationship with Tom in 2001, Nicole has been living her best life. She won an Oscar and found love with Keith Urban!
Britney Spears and Charlie Ebersol

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Sandra Bullock and Ryan Gosling Wow, Miss Congeniality meet Mr. Congeniality. Can you name this cringey celeb couple?
Millie Bobby Brown and Jacob Sartorius
Sandra Bullock and Ryan Gosling
OMG, do NOT tell us you forgot about Sandra Bullock and Ryan Gosling! Like, a billion years ago (aka 2002), Sandra and Ryan started dating after meeting on the set of "Murder by Numbers." Everyone freaked TF out over their 16-year age difference.
Nikki Bella and John Cena
Channing Tatum and Jenna Dewan Tatum

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Scott Disick and Kourtney Kardashian Yuh, we still keep up with these two. Can you name this cringey celeb couple?
Michelle Rodriguez and Zac Efron
Chelsea Handler and 50 Cent
Kim Kardashian and Nick Lachey
Kourtney Kardashian and Scott Disick
Because of "Keeping Up With the Kardashians," we've had a front-row seats to a lot of cringey-AF moments between Kourtney Kardashian and Scott Disick. The former couple have three children together and share parenting duties.

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Ryan Reynolds and Scarlett Johansson Too beautiful to last, we guess. Do you remember this odd-AF celebrity couple?
Ryan Reynolds and Scarlett Johansson
Ryan Reynolds high-key has a thing for blondes. Before he found love with Blake Lively, he was married to Scarlett Johansoon. Was that a worse decision than making "Green Lantern?" Tbh, it's hard to say.
Pamela Anderson and Tommy Lee
Denise Richard and Charlie Sheen
Johnny Depp and Amber Heard

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Renée Zellweger and Jim Carrey Huh, seems like "on set" is the place to score dates. What are the names of this cringey celeb couple?
Goldie Hawn and Kurt Russell
Sean Penn and Madonna
Arnold Schwarzenegger and Maria Shriver
Renée Zellweger and Jim Carrey
Jim Carrey totally knows where our funny bone is, and apparently, he used to make Renée Zellweger laugh too. After connecting on the set of "Me, Myself and Irene," the two dated for a year and a half.

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Reese Witherspoon and Ryan Phillippe Ugh, this is why we can't have nice things. Can you name this cringey celeb couple?
Rihanna and Shia LeBeouf
Reese Witherspoon and Ryan Phillippe
If we had a nickel for every time we watched "Cruel Intentions," well, we'd have A LOT of nickels. Reese Witherspoon and Ryan Phillippe were ADORABLE, but then he had to go and cheat on her. Why?!
Patrick Wilson and Jennifer Love Hewitt
Moby and Natalie Portman

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Miley Cyrus and Liam Hemsworth And we really thought these two had something special. Do you remember this odd-AF celebrity couple?
Grimes and Elon Musk
Miley Cyrus and Liam Hemsworth
After less than one (yes, one!) year of marriage, Miley Cyrus and Liam Hemsworth called it quits. Tbh, we're still reeling. Apparently, the two just had very different lives and were growing in different directions (one of those different directions was Kaitlynn Carter).
Amy Poehler and John Stamos
Lady Gaga and Taylor Kinney

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Madonna and Tupac We're throwing it back for this one. Do you remember this odd celebrity couple?
Madonna and Tupac
Madonna's relationship with Tupac was so low-key you might not have even known about it. In fact, Madonna didn't come out and confirm the two were a couple in the '90s until 2015. Better late than never?
Jeff and Mackenzie Bezos
Toni Braxton and Birdman
Kourtney Kardashian and Younes Bendjima

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Tori Spelling and Dean McDermott
Lindsay Lohan and Samantha Ronson
Tobey Maguire and Rashida Jones
Yuh, he was Spiderman before Tom Holland (and Andrew Garfield). Before he ever shot webs out of his wrists, Tobey Maguire and Rashida Jones dated for three years in the late '90s. We can't believe this, but apparently, he broke up with her?!
Jack Nicholson and Anjelica Huston

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Tom Cruise and Katie Holmes Lol, this dude keeps cropping up with different women. Who are the people in this bizzare celeb couple?
Jenna Dewan and Justin Timberlake
Leonardo DiCaprio and Gisele Bündchen
Tom Cruise and Katie Holmes
Tbh, when Katie Holmes was with Tom Cruise, she gave us major Stepford Wife vibes. We were big relieved when she divorced him and left with little Suri. Now (like all Tom's other exes), she seems to be living her best life!
Josh Hutcherson and Vanessa Hudgens

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