1. Rihanna and Shia LeBeouf
   Reese Witherspoon and Ryan Phillippe
2. Patrick Wilson and Jennifer Love Hewitt
   Moby and Natalie Portman

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?!

1. Kristen Stewart and Robert Pattinson
   Luke Wilson and Gwyneth Paltrow
2. Madonna and Michael Jackson
   Miley Cyrus and Nick Jones

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.

1. Kim Basinger and Alec Baldwin
   Jennifer Lopez and Ben Affleck
2. Kate Moss and Johnny Depp
   Gwyneth Paltrow and Brad Pitt

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.

1. Charlize Theron and Sean Penn
   Kim Kardashian and Kris Humphries
2. Miranda Lambert and Blake Shelton
   Gwen Stefani and Gavin Rossdale

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.

1. Tyra Banks and Drake
   Brooke Shields and Nicolas Cage
2. Brad Pitt and Angelina Jolie
   Jared Leto and Cameron Diaz

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.

1. Drew Barrymore and Christian Bale
   Justin Timberlake and Fergie
2. Ariana Grande and Pete Davidson
   Pink and Joey Fatone

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.

1. Jenna Dewan and Justin Timberlake
   Leonardo DiCaprio and Gisele Bündchen
2. Tom Cruise and Katie Holmes
   Josh Hutcherson and Vanessa Hudgens

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!

1. Aaliyah and Jay Z
   Ashley Olsen and Lance Armstrong
2. 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.

1. Victoria Adams and David Beckham
   Will Smith and Jada Pinkett
2. 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).

1. Demi Moore and Bruce Willis
   Lenny Kravitz and Lisa Bonet
2. Michael Cera and Aubrey Plaza
   Johnny Depp and Winona Ryder

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!

1. Katy Perry and Russell Brand
   Nicole Kidman and Tom Cruise
2. Courtney Love and Kurt Cobain
   Iman and David Bowie

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?

1. Taylor Swift and Tom Hiddleston
   Amanda Seyfried and Justin Long
2. Kaley Cuoco and Ryan Sweeting
   Megan Fox and Brian Austin Green

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.

1. Mel Gibson and Oksana Grigorieva
   Shia LaBeouf and Hilary Duff
2. Renee Zellweger and Kenny Chesney
   Madonna and Sean Penn

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."

1. Jennifer Lopez and P. Diddy
   Gigi Hadid and Zayn Malik
2. Usher and Grace Miguel
   Jennifer Aniston and Justin Theroux

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!

1. Tom Cruise and Katie Holmes
   Ellen DeGeneres and Portia de Rossi
2. Kylie Jenner and Jaden Smith
   Kristen Stewart and Robert Pattinson

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.

1. Justin Timberlake and Fergie
   Jennifer Aniston and Vince Vaughn
2. Joaquin Phoenix and Liv Tyler
   Matt Damon and Winona Ryder

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.

1. Adele and Simon Konecki
   Lady Gaga and Christian Carino
2. Mila Kunis and Macaulay Culkin
   Brie Larson and Alex Greenwald

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.

1. Nick Lachey and Jessica Simpson
   Brad Pitt and Angelina Jolie
2. 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.

1. Lena Dunham and Jack Antonoff
   Ciara and Bow Wow
2. Fergie and Josh Duhamel
   Chris Pratt and Anna Faris

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!

1. Ryan Phillippe and Demi Lovato
   Lance Armstrong and Kate Hudson
2. 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.

1. Jennifer Aniston and Brad Pitt
   Emily Blunt and Michael Bublé
2. Britney Spears and Justin Timberlake
   Jay-Z and Beyoncé

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.

1. Zooey Deschanel and Jacob Pechenik
   Demi Moore and Ashton Kutcher
2. Billie Lourd and Taylor Lautner
   Nicki Minaj and Meek Mill

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.

1. Ryan O'Neal and Farrah Fawcett
   Keira Knightley and Jamie Dornan
2. Carrie Fisher and Paul Simon
   Sarah Jessica Parker and Robert Downey Jr.

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."

1. Jessica Biel and Chris Evans
   Selena Gomez and Justin Bieber
2. George Clooney and Amal Alamuddin
   Blake Shelton and Gwen Stefani

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.

1. Nick Lachey and Jessica Simpson
   Kristen Johnson and Ryan Reynolds
2. Leonardo DiCaprio and Blake Lively
   Sandra Bullock and Matthew McConaughey

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.

1. Michelle Rodriguez and Cara Delevingne
   Tom Cruise and Cher
2. Gwyneth Paltrow and Brad Pitt
   Edward Norton and Courtney Love

"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.

1. Jennifer Aniston and Paul Rudd
   Katie Couric and Bob Saget
2. Tom Holland and Zendaya
   Stella Maxwell and Kristen Stewart

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."

1. Bradley Cooper and Irina Shayk
   Kendall Jenner and Ben Simmons
2. 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.

1. Michelle Rodriguez and Zac Efron
   Chelsea Handler and 50 Cent
2. 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.

1. Sarah Jessica Parker and Robert Downey Jr.
   Johnny Depp and Amber Heard
2. Jennifer Garner and Ben Affleck
   Kim Kardashian and Kris Humphries

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?

1. Katie Holmes and Jamie Foxx
   Tom Cruise and Penélope Cruz
2. Miley Cyrus and Liam Hemsworth
   Lili Reinhart and Cole Sprouse

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.

1. Kiefer Sutherland and Julia Roberts
   Owen Wilson and Sheryl Crow
2. 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.

1. Natalie Portman and Jake Gyllenhaal
   Kate Hudson and Alex Rodriguez
2. Selena Gomez and Justin Bieber
   Angelina Jolie and Billy Bob Thornton

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?

1. Ryan Reynolds and Scarlett Johansson
   Pamela Anderson and Tommy Lee
2. Denise Richard and Charlie Sheen
   Johnny Depp and Amber Heard

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.

1. Nick Jonas and Olivia Culpo
   Emma Roberts and Evan Peters
2. Nicole Kidman and Tom Cruise
   Britney Spears and Charlie Ebersol

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!

1. Goldie Hawn and Kurt Russell
   Sean Penn and Madonna
2. 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.

1. Millie Bobby Brown and Jacob Sartorius
   Sandra Bullock and Ryan Gosling
2. Nikki Bella and John Cena
   Channing Tatum and Jenna Dewan Tatum

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.

1. Madonna and Tupac
   Jeff and Mackenzie Bezos
2. Toni Braxton and Birdman
   Kourtney Kardashian and Younes Bendjima

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?

1. Tori Spelling and Dean McDermott
   Lindsay Lohan and Samantha Ronson
2. Tobey Maguire and Rashida Jones
   Jack Nicholson and Anjelica Huston

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?!

1. Grimes and Elon Musk
   Miley Cyrus and Liam Hemsworth
2. Amy Poehler and John Stamos
   Lady Gaga and Taylor Kinney

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).