Can You Name These Cringey Celeb Couples?


By: Alex Wittman

7 Min Quiz

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!

These two had the GOAT couple nickname. Can you name this cringey celeb couple?

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.


Teenage vampires, YKTV. Can you name this cringey celeb couple?

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.


People this beautiful should legally not be allowed to date. Do you remember this odd-AF celebrity couple?

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.


This star was born, but then it went supernova. Who are the people in this bizzare celeb couple?

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.


Oh, you know she's gonna write a song about this. Can you name this cringey celeb couple?

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.


Major Disney vibes, tho. Can you name this cringey celeb couple?

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."


We love them as individuals but together is another story. Can you name this cringey celeb couple?

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.


OMG, we almost forget this was a thing. Who are the famous faces in this cringey celeb couple?

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?


Yuh, she's on this quiz a couple times but with different dudes. Who are the famous faces in this cringey celeb couple?

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!


This was a match made in awkward-AF heaven. Can you name this cringey celeb couple?

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!


This has to be one of the shortest marriages in the history of Hollywood. Can you name this cringey celeb couple?

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.


Awww, young love (barf). Can you name this cringey celeb couple?

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.


Wait, these two were sort of adorable (just sort of, though). Can you name this cringey celeb couple?

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.


Lol, she definitely has a type. What are the names of this cringey celeb couple?

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.


Tbh, we still can't believe this happened. Can you name this cringey celeb couple?

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.


This couple low-key dated forever. Can you name this weird celeb couple?

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.


We knew this was too good to last. What are the names of this cringey-AF celeb couple?

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.


Wait, they're kinda cute. What are the names of this celeb couple?

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."


Not even making music together could save this relationship. Can you name this cringey celeb couple?

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!


These two could have totally worked out. Who are the people in this bizzare celeb couple?

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.


We hardly recognize the dude without his whips and chains. Can you name this cringey celeb couple?

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."


No cap, these two look like they could be brother and sister. Do you remember this odd-AF celebrity couple?

"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.


People freaked over this age difference. Do you remember this odd celebrity couple?

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.


It doesn't get more random than this. What are the names of this cringey celeb couple?

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.


Same name, different spellings. Can you name this cringey celeb couple?

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.


Ah, we can't stop laughing. Do you remember this weird (that's an understatement) celeb couple?

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).


Young Iron Man in love. Can you name this cringey celeb couple?

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?


As long as we live, we will never forget their TV show. Can you name this cringey celeb couple?

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.


We want these two to make one more song together, plz. What are the names of this cringey-AF celeb couple?

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?


Since this relationship ended, we haven't seen stranger things (get it?). Can you name this cringey celeb couple?

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.


Not him again. What are the names of this cringey-AF celeb couple?

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!


Wow, Miss Congeniality meet Mr. Congeniality. Can you name this cringey celeb couple?

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.


Yuh, we still keep up with these two. Can you name this cringey celeb couple?

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.


Too beautiful to last, we guess. Do you remember this odd-AF celebrity couple?

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.


Huh, seems like "on set" is the place to score dates. What are the names of this cringey celeb couple?

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.


Ugh, this is why we can't have nice things. Can you name this cringey celeb couple?

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?!


And we really thought these two had something special. Do you remember this odd-AF celebrity couple?

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).


We're throwing it back for this one. Do you remember this odd celebrity couple?

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?


Oh, hello, '90s. Can you name this cringey celeb couple?

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?!


Lol, this dude keeps cropping up with different women. Who are the people in this bizzare celeb couple?

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!


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