#30. Liam Hemsworth & Miley Cyrus
Liam Hemsworth and Miley Cyrus were one of the public’s favorite celebrity relationships ever. Whenever the couple was spotted, the two seemed happily in love, but after a couple of years together, things started falling apart.
They even got engaged in 2012 but split up and spent a year apart, allegedly due to Miley’s career path change. They reconciled in 2013 and renewed their engagement before splitting up once more. Then, in 2018, the pair tied the knot, and in a not-so-surprising twist, they filed for divorce a few months later.
#29. Andrew Garfield & Emma Stone
Andrew Garfield and Emma Stone met on the set of The Amazing Spiderman and became the cutest couple ever. The pair were together for three years before they got engaged, and it truly seemed like they would be together forever.
They shockingly broke up in 2015 for reasons we don’t know. But just as we were all losing hope, they got back together in 2017. Their reunion was brief, however, because they broke up one year later. Now, Emma is engaged to Dave McCary, and Andrew is single.
#28. Pink & Carey Hart
Pink and Carey Hart's relationship started almost 20 years ago, there have been many bumps in the road for these two. They started dating in 2001 and got engaged in 2003 but broke up shortly after.
In 2005, Pink wanted him back and surprised him at one of his motocross competitions and proposed to him, to which he said yes. The couple got married and were together until 2008 when they broke up once more. However, they've been together since 2009, so it seems they figured out how to make it work.
#27. Zayn Malik & Gigi Hadid
Zayn Malik had an on-and-off relationship with fellow singer Perry Edwards for four years and even got engaged, but that relationship ended for good when he started dating model Gigi Hadid, with whom he also had a tumultuous relationship.
The couple split up and got back together about three times in one year, until they supposedly ended things for good in 2017. Then, in 2018, the couple was seen together once more, but sadly, that only lasted for a couple months. Both of them are single now, so who knows what will happen!
#26. Drake & Rihanna
Drake and Rihanna’s relationship history is kind of strange, mostly because Rihanna denied it for years, while Drake tried hard to let the world know they had been an item. The truth is that they were briefly together in 2009 before Rihanna told Drake they were better off as friends.
Drake never really got over the breakup and pursued Rihanna for years, until she agreed to get back together in 2015. That didn’t last long, however, and Drake even attempted to win her back by announcing that he loved her at the 2016 VMA’s. Allegedly, that only made Rihanna like him less.
#25. Justin Timberlake & Jessica Biel
It might seem unbelievable now that they’ve been together for so long, but Justin Timberlake and Jessica Biel actually broke up a couple months after they started dating. Allegedly, Timberlake wasn’t so big on commitment, but then he changed his mind.
The couple got married in 2012 and welcomed their first son, Silas, in 2015. However, in 2019, pictures of Timberlake holding hands with a co-star surfaced, and that put a strain on their marriage. However, they have stayed together after that bump in the road.
#24. Chris Evans & Minka Kelly
There was a time when Chris Evans had a long, on-and-off relationship with actress Minka Kelly. The two got together in 2007 and dated for five years until they split up in 2012. Since their breakup was around the time Evans got the Captain America role, many believe that his fame broke up their relationship.
Regardless of why they broke up, the couple got back together in 2013 and tried to make it work once more, but that only lasted for a few months. After 7 years of being on and off, the couple finally called it quits.
#23. Justin Bieber & Hailey Baldwin
After Justin Bieber ended things with on-again-and-off-again ex-girlfriend Selena Gomez, he got together with model Hailey Baldwin. People thought it was just a rebound and that it wouldn’t last very long —and it didn’t. Bieber and Gomez got back together in 2017 for a brief period of time.
However, Bieber and Baldwin got back together in 2018 and became inseparable. They quickly got engaged and just a few months later, they tied the knot. Although there have been rumors about trouble in paradise, they seem to be going strong.
#22. Katy Perry & Orlando Bloom
After both Katy Perry and Orlando Bloom divorced their exes, the couple got together in secret. They managed to hide their relationship pretty well, until the paparazzi caught them at a beach in 2016. They seemed to be a pretty solid pair, but they split in 2017.
On New Year’s Eve, 2018, the couple got together to celebrate in Japan, but they didn’t officially get back together. Two months later, however, they confirmed their reconciliation and even got engaged. They haven’t set a date for their wedding yet, but we can’t wait.
#21. Jude Law & Sienna Miller
Jude Law and Sienna Miller were once the most attractive couple in the universe, and it seemed as though nothing could break them apart. After a year of dating, they got engaged, but then, it was discovered that Law had cheated on her with the nanny.
Even though they tried to work things out, they ended up breaking up in 2006. Then, in 2009, they got back together, to the surprise of everyone. In 2011, however, things ended for good, and both moved on to date other people.
#20. Demi Lovato & Wilmer Valderrama
Demi Lovato and Wilmer Valderrama had a very low-key relationship for many years, and it had its ups and downs. They first got together in 2010 and dated for two years before splitting up. They dated other people here and there, and then they got back together in 2014.
All throughout the relationship, Lovato's health issues reportedly took a toll on their relationship. The singer publicly acknowledged that Valderrama was a huge support all along. In 2016, they broke things off for good, sadly.
#19. Chris Evans & Jenny Slate
Who knew Captain America would be here twice? This time it's for his on-and-off relationship with comedian Jenny Slate. The two filmed a movie together and fell in love on set in 2015. Even though they tried to keep things private, the media coverage on their relationship allegedly took a toll on them.
After two years together, they split up, but not for long. Just a few months later and after flirting back and forth on Twitter, they reconciled, but it only lasted six months. Rumor has it that Evans did not want to pop the big question, so Slate decided to end it.
#18. Megan Fox & Brian Austin Green
Megan Fox and Brian Austin Green first got together in 2004 and got engaged in 2005. They were engaged for four years before they called the engagement off. And just when everyone thought it was over for good, they got back together and got re-engaged a year later.
They enjoyed a few happy years of marriage and had three kids together before they found themselves in trouble again. In 2015 they filed for divorce, but a year later they got back together. However ,it wasn’t until 2019 that Fox finally asked the court to dismiss the petition.
#17. Sammi Giancola & Ronnie Magro-Ortiz
You might remember Sammi "Sweetheart" Giancola and Ronnie Magro-Ortiz from the original Jersey Shore, particularly, them being a super toxic couple. They started dating in 2009 and had their first official breakup in 2010.
After many will-they-won’t-they moments, they got back together in 2011. Through many ups and downs, they managed to stay together until 2016, when they ended things for good, but when it comes to these two, who knows…
#16. Chloe Grace Moretz & Brooklyn Beckham
Chloe Grace Moretz and Brooklyn Beckham had a very low-profile relationship, yet there was a lot of drama behind the scenes. After meeting at Paris Fashion Week in 2014, the two dated for two years before they actually confirmed they were together in 2016.
Sadly, shortly after confirming it, they broke up. They got back together an year later, but that only lasted another year. After going back and forth a few more times, they officially ended things in April 2018 when Moretz ditched the “B” ring she always wore (B for “Brooklyn”, of course).
#15. Richard Burton & Elizabeth Taylor
Richard Burton and Elizabeth Taylor’s relationship was big in the 1960s. As one of the most prominent couples of their time, they made headlines after they got together on the set of Cleopatra. They were married for 10 years, but then things went south.
They remarried a year after their divorce in 1975, but then got divorced again a year later. Taylor went on to have a total of 8 husbands and Burton married 5 times. Before he passed away in 1984, he sent a letter to her confessing that he still loved her.
#14. Kourtney Kardashian & Scott Disick
Kourtney Kardashian and Scott Disick’s rollercoaster of a relationship was well documented on Keeping Up with the Kardashians for over 15 seasons. Ever since they started dating, there were rumors that Scott was cheating on Kourtney, which caused them to split up and get back together many times.
In spite of their problems, the couple reconciled when their first son, Mason, was born. After several breakups and reconciliations, they officially split in 2016. They maintain a good relationship and share custody of their children.
#13. Wiz Khalifa & Amber Rose
Wiz Khalifa and Amber Rose got together in 2011 and there began an intense relationship between the two. Rose even had his face tattooed on her arm! In 2013, the couple got married and had a child together, but rumors of Khalifa’s cheating led to their breakup.
On top of the rumors, Rose publicly accused him of cheating, and then it was over. For the sake of their son, the couple tried many times to reconcile and make it work, but in 2018, they officially announced that there was nothing going on between them anymore.
#12. Kate Middleton & Prince William
They seem like a super solid couple nowadays, but Prince William and Kate Middleton weren’t always like that. The couple met in college and dated for a couple years before calling it quits in 2007. After two years apart, they reconnected and rekindled their romance.
As we all know, they got married in 2011 and had an iconic, huge televised wedding. The happy couple has three kids together and seem to be doing fine. In 2019, rumors of William cheating went around, but the couple quickly shot them down.
#11. Jennifer Lopez & Casper Smart
Jennifer Lopez got together with backup dancer Casper Smart after her divorce from Marc Anthony in 2011, and it seemed like it was going to be a brief romance. However, it was actually a tumultuous relationship that lasted until 2016.
During all those years, the couple broke up a few times and then got back together, though nobody knows why. Even when asked about what happened, Lopez dodged the question. Now, Lopez is engaged to Alex Rodriguez.
#10. Rob Kardashian & Blac Chyna
Rob Kardashian and Blac Chyna had one of the most explosive celebrity relationships of all time. Chyna was previously together with rapper Tyga, who was dating Kylie Jenner, Rob’s younger sister. This made things very awkward and the Kardashian family didn’t like Chyna at all.
Although their relationship started on the wrong path, the two got engaged 10 weeks later and a month later they were expecting their first child together —a baby girl Dream Renée. However, the wedding was called off and from that point on, things went awfully awry. On July 2017, after Rob accused her of infidelity, a custody battle over their child began.
#9. Amy Winehouse & Blake Fielder-Civil
Amy Winehouse and Blake Fielder-Civil had a very complicated relationship that lasted several years. The two got together in 2005 and began a very volatile romance that had very high highs and very low lows. In 2007, the couple got married in secret and Winehouse got his name tattooed.
But their bad habits and erratic behavior caused their relationship to implode more than once. They were on and off for two years, until they got divorced in 2009. It wasn’t over for Winehouse, however, as she pursued Fielder even after he had moved on with someone else. After a year, she gave up.
#8. Emma Roberts & Evan Peters
Emma Roberts and Evan Peters started out as a super adorable couple, but the dark side of their relationship started to show very quickly. One year into their relationship, Roberts was arrested for domestic abuse, but was released after he decided not to press charges.
After the incident, the couple tried making it work with many ups and downs in between. They got engaged in 2013 but broke up in 2015 without having tied the knot. Only a couple months later, they were together again, and then they broke up once more, this time for good.
#7. Lindsay Lohan & Samantha Ronson
Lindsay Lohan had a whirlwind romance with DJ Samantha Ronson from 2008 to 2009, but somehow, it felt like they were together for ages. Perhaps it’s because they broke up and reconciled so many times during that short period.
Lindsay dated Ronson during her heavy partying days Their relationship was catastrophic and took a toll on both of them. They were basically on the cover of every magazine for all the wrong reasons, and the relationship couldn’t survive anymore.
#6. Katy Perry & John Mayer
John Mayer has dated several female celebrities and one of them is Katy Perry. After Perry divorced Russel Brand, she got together with Mayer. Even though they didn’t officially break up, there were always separation rumors floating around and apparently, things weren’t very good between them.
In 2013, however, they did break up, but it only lasted three months. Then in February 2014, although there were engagement rumors going around, the couple officially split and this time, for good. As we know, Perry went on to date Orlando Bloom, and Mayer kind of faded into obscurity.
#5. Ryan Gosling & Rachel McAdams
Ryan Gosling and Rachel McAdams were an on-screen couple on The Notebook, so fans couldn’t be happier when these two started dating in real life after the movie was released. But the truth is that their real-life love was very different from the movie.
During filming, they reportedly hated each other, and Gosling even tried to get her fired. Eventually, they discovered that they had feelings for each other, and they began dating. Their relationship came to an end three years later in 2007, and in 2013, they reportedly got together again for a very brief reunion.
#4. Jennifer Lawrence & Nicholas Hoult
When they first got together in 2010, neither Jennifer Lawrence nor Nicholas Hoult were big stars, so they enjoyed pretty private lives. Then, in 2012, Lawrence became an A-lister thanks to her role in The Hunger Games, and that took a toll on their relationship.
The couple broke up a year later and reportedly tried to make it work several times after that. But Lawrence’s fame and spending a lot of time apart made it impossible. They briefly reunited when they both were in X-Men: Days of Future Past, but that only lasted a few months.
#3. Ben Affleck & Jennifer Garner
Ben Affleck and Jennifer Garner became an official couple in 2004 after a lot of back and forth, and only a year after that, they got married. They had a whole decade of happy times and had three children together, but then, things started to get complicated.
In 2016, the couple broke up, to the surprise of the whole world. But a few months after that, they were seen attending couples’ counseling and trying to work things out. They initially called off their divorce in 2017, but in 2018, they finalized it.
#2. Kylie Jenner & Tyga
Kylie Jenner and Tyga’s relationship was problematic from the beginning. Rumors that they were dating started when Kylie was 14 and Tyga was 25, which creeped a lot of people out. They always denied it but then, the day Kylie turned 18, the couple announced they were together.
The couple then dated on and off for years and rumors of Tyga’s cheating were always around. After countless ups and downs, they broke up for good in 2017. Allegedly, Tyga still wanted to pursue Kylie but it was too late, because she then got together with Travis Scott.
#1. Justin Bieber & Selena Gomez
Justin Bieber and Selena Gomez are almost as famous for their toxic on-and-off relationship as they are for their music. The two were each other’s first love and enjoyed a few years of a teenage romance before they broke up…for the first time.
Although there were many rumors about why they kept splitting up, the real reasons were never revealed. Now, Justin is married to Hailey Baldwin and Selena has reportedly moved on —and written a whole album about it— but who knows, we might see more of these two in the future!