On-Again, Off-Again Celebrity Couples Who Just Can't Call it Quits

Prince Williams and Kate Middleton

It seems a bit silly to call the future King and Queen of England and on again, off again couple but - at least in their early days - they were. Even just a few years before the royal wedding, these two had called it quits.

Prince William and Kate Middleton met at Cambridge University and began dating around 2001. For a few years, the media circus never knew what to think. The couple broke up in 2007 for reasons unknown only to reunite that year and become engaged in 2010. Recent infidelity rumors have brought the health of this relationship back into the spotlight.

Kylie Jenner and Travis Scott

In April 2017, Kylie Jenner met Travis Scott at Coachella. In February 2018, they had a baby, Stormi, before splitting up for the first time. Then the pandemic hit. The couple decided to quarantine together for the sake of their child and things got steamy again.

By September 2021, the couple announced they were expecting their second child. Jenner and Scott's son was born in February 2022. Sadly, the love of two kids wasn't enough for these cats, who decided to call it quits again in January 2023. Since then, Jenner has been seen kissing Timothee Chalamet.

Khloe Kardashian and Tristan Thomas

In 2016, Khloe Kardashian began dating basketball player Tristan Thompson. She gave birth to their daughter, True Thompson, in April 2018. It later emerged that Thompson had cheated on Kardashian during her pregnancy. In February 2019, the couple split after Thompson was revealed to have slept with Kylie Jenner's best friend, Jordyn Woods.

In August 2020, they started dating again after quarantining together during the pandemic. And in July 2022, it was announced that Kardashian and Thompson were expecting a baby boy via surrogacy. Tatum Thompson was born later that month. The good times didn't last forever though as the couple split again later that year.

Justin Bieber and Selena Gomez

Long before Justin Bieber and Selena Gomez were even an item, the singer had expressed his feelings for her in interviews. Biebs couldn't believe his luck when those feelings were reciprocated. These two had the world at their feet, so what went wrong?

Justin Bieber was trying to achieve domesticity in a period of his life when supermodels were throwing themselves at him in every country. He and Gomez struggled to find the right balance with the level of fame they had, splitting and making up four times between 2018, when Biebs ran off and married Hailey Baldwin.

Cardi B and Offset

Cardi B began dating rapper Offset in early 2017. By October that same year, the two were engaged. In July 2018, they welcomed their first child, a daughter, into the world. Unfortunately, Cardi announced their divorce and separation by Christmas.

Then at the Grammy Awards the following February, the couple made a public appearance together. Things went swimmingly for over a year... and then they split again in September 2020. In June 2021, Cardi announced she was pregnant with her second child. The father, of course, was Offset. Since then, as far as we know, they have remained together.

Jennifer Lopez and Ben Affleck

Jennifer Lopez and Ben Affleck have the biggest gap of any couple on this list but, technically, they were off and now they are on. The rules are the rules! Bennifer 2.0 was something nobody was expecting back in 2021.

The couple first got together in the early 2000s when Jennifer was one of the hottest singers on the planet and Affleck was one of the hottest actors. They kept things going until 2004, after which Lopez married Marc Anthony while Ben married Jennifer Garner. Divorced and ready to mingle in 2021, the pair reconciled and have been inseparable since.

Gabrielle Union and Dwayne Wade

What do NBA player Dwayne Wade and actress Gabrielle Union have in common? They're both involved in an on again, off again relationship! While most people's fizzle out after three to four years, their turbulent relationship has recently approached the 15-year mark.

The pair first hooked up in 2008 but split up around 2012. In the gap, Dwayne fathered a child with another woman, which broke Union's heart. However, in 2014 the couple reunited and have stayed together since. The two have blended their separate families as one and, according to Instagram, live a very happy life!

Megan Fox and Brian Austin Green

Megan Fox and Brian Austin Green got together when she was just 18 years old and he was 30. Together, and not together, they had one of the most confusing and erratic relationships in recent Hollywood memory. In 2006 they got engaged, cancelled it in 2009, then got re-engaged in 2010.

They were secretly married the same year and had two children. By 2015, Fox had filed for divorce. In 2016, however, she was pregnant with her and Brian's third child. She withdrew the divorce papers in 2019 only to call it quits once more in 2020. Fox has since been seen enjoying the ultimate rebound in Machine Gun Kelly.

Gigi Hadid and Zayn Malik

Zayn Malik wasn't super committed to Lil Mix's Perrie Edwards, so he dumped her for supermodel Gigi Hadid in 2015. Between then and 2020, the couple broke up at least two times but decided to go the extra mile after their daughter, Khai, was born in 2020.

For a while (a single year) the relationship flourished. The whole thing came to an end in October 2021 after Zayn Malik had an altercation with Gigi's mother Yolanda Hadid over personal space issues. During the fracas, Malik allegedly hit Yolanda. He and Gigi are yet to reconcile, though they manage to co-parent Khai.

Ryan Seacrest and Shayna Taylor

Subject to the rumor hill like few other presenters, Ryan Seacrest has actually been dating in private for years now. He and model Shayna Taylor dated for almost eight years on and off, breaking up a total of three times between 2013 and 2020.

Before that, Seacrest had another on-and-off relationship with Sara Jean Underwood. And then again with Julianne Hough. After breaking up with Taylor, Seacrest is reported to be dating a 25-year-old Instagram model named Audrey Paige. Let's see how long that one lasts.

Justin Timberlake and Jessica Biel

Not all celebrities meet on film sets. Some of them meet casually, like us normal folk. Justin Timberlake and Jessica Biel, both huge stars in their own right, were introduced at a friend's birthday party. If that isn't relatable, we don't know what is.

This occurred sometime in 2007. They then dated until 2011, at which point they confirmed their breakup to People magazine. The same year they rekindled and got engaged and have been married since 2012. They share two sons. Never say never, though - things could change!

Miley Cyrus and Liam Hemsworth

While filming The Last Song in 2009, Cyrus began an on again, off again relationship with Aussie hunk Liam Hemsworth. The pair would try and struggle to make things work during Cyrus' controversial Bangerz era in the mid 2010s.

Eventually, Cyrus grew her hair back out, gave up smoking (temporarily), and decided to tie the knot with Hemsworth in an intimate Nashville service in 2018. Barely out of the honeymoon period, the couple divorced in 2020 in what was said to be a mutual decision.

Rihanna and Drake

What exactly went on between Rihanna and Drake and how it ended isn't really known but they were definitely an item. The two were seen getting cosy on and off for years, sharing the red carpet and even collaborating on songs together.

Drake has gone on record as saying Rihanna is his dream girl. He once rented a billboard in her honor. The couple even got matching tattoos. However, the relationship was widely seen as toxic, and the couple finally hit the off switch. Rihanna moved on to A$AP Rocky and had two children.

Sylvester Stallone and Jennifer Flavin

Longtime lovers Sylvester Stallone and Jennifer Flavin finally stumbled in the summer of 2022 and announced their plans to divorce by August. In a statement, Stallone said, "I love my family. We are amicably and privately addressing these personal issues."

By September, the couple had cancelled their papers and reconciled. "They decided to meet back up at home, where they talked and were able to work out their differences. They are both extremely happy," the actor's rep told Page Six.

Christine Taylor and Ben Stiller

After splitting in 2017, Ben Stiller and Christine Taylor reunited in 2022. Taylor decided it was best for Stiller to move back in with her and their two kids during the first leg of the pandemic. Things blossomed from there.

"I think we have a respect for the ways that we're similar and the ways we're different. And I think accepting that, you can really appreciate someone more because you're not trying to get them to change for you," Stiller said in an interview. Wise words!

Miguel and Nazanin Mandi

The singer and actress announced her split from Miguel in September 2021. The couple had dated for ten years before getting engaged in 2016, which is a pretty hefty amount of time. They tied the knot in 2018. The split, thankfully, only lasted a few short months.

Neither Miguel nor Nazanin Mandi could keep their hands off each other. Though neither fully confirmed their reunion, they shared photos of what looked like a cosy winter getaway to the Amangiri in Canyon Point, Utah in January 2022. Hopefully things are still going strong!

Winnie Harlow and Kyle Kuzma

These two first connected in May 2020 after the Washington Wizards forward slid into Harlow's DMs on Instagram. The couple first split in 2021, though they were spotted in December of that year having an intimate and romantic date in New York City.

In February 2023, Harlow confirmed that Kuzma was once again her boyfriend by sharing pictures of the two celebrating Valentine's Day. In the caption, she referred to him as "My Cupid." Keep your eyes peeled for more updates in this tantalising saga!

Jill Martin and Erik Brooks

Jill Martin and financier squeeze Erik Brooks got engaged in 2019 but split the following year, after the pandemic kept them apart. In November 2021, Martin announced the two had reunited and gotten engaged once again. In September 2022, they were finally married.

"It took me 45 years to find my fairy tale. When I realized I was confident on my own, that's when I knew Erik and I were ready to get back together," Martin later reflected. "The realistic version of my fairy tale was ready to be written." How sweet!

Dave and Odette Annable

Dave Annable, of The Brothers & Sisters fame and Odette Annable of Supergirl fame, tied the knot in a private ceremony in Ojai, just north of Los Angeles, in October 2010. After nine years of marriage, however, the pair announced that they were separating.

By August 2020, though, the couple were posting identical Instagram photos and captions, confirming their reunion in a saucy selfie. 2020: it ain't all bad news. #TheAnnables," they wrote with the snapshot. In the comments of his wife's post, Dave teased: "My post is better." They share a daughter, Charlie Mae.

Kelly Ripa and Mark Consuelos

Kelly Ripa might be someone you have characterised in your own head as a bit beige and inoffensive. She seems like a company woman in all areas of life, but she's made some pretty wild decisions over the years. Probably none more so than her decision to break up with her boyfriend Mark Consuelos right before marrying him.

"Right before we got married, we broke up," the Live With Kelly and Ryan host told Emma Diamond and Julie Kramer on the debut episode of Betches' Comments by Celebs podcast. "We broke up and we got back together the day before we went off and eloped. Yeah, we eloped. We went to Vegas and got married."

Dax Shephard and Kristen Bell

Years before they became one of Hollywood's couple success stories and parents to daughters Lincoln and Delta, Dax Shepard and Kristen Bell were all over the place in terms of stability. "We were dating for about three months," Bell explained. "He sat me down and said, 'I can't have this right now. I think you're wonderful, but I am still dating other people.'"

Shepard soon realized what a mistake he'd made and confessed: "'I don't know what I was thinking. I was dating someone else but they're just not as interesting as you, and I don't know what I'm doing.'" Bell hasn't let him live down his blunder. "I still always remind him of when he broke up with me."

Sharon and Ozzy Osborne

The former X Factor Judge and The Talk co-host, Sharon Osborne has addressed her long and turbulent relationship with Black Sabbath legend Ozzy Osborne, both in print and on camera. After splitting up due to his infidelity, Sharon admitted she had reconciled with the rocker.

"I forgive," she told the studio audience. "It's going take a long time to trust, but we've been together 36 years, 34 of marriage. I just can't think of my life without him." Osborne added that Ozzy was a "dirty dog" and that "He's gonna pay big." Yikes.

Patrick and Jilian Dempsey

Patrick Dempsey married Jillian Fink July 1999. For years, the two enjoyed a seemingly perfect marriage with their three children but in 2015, Jilian filed for divorce. The Grey's Anatomy star's commitment to the racetrack was said to have been a huge issue for the couple.

A year later, the couple reconciled and called off the divorce proceedings. Dempsey revealed in a 2022 interview: "You have to work at everything. And you cannot do everything. Something has to be sacrificed." Wise words that have apparently saved his marriage, good for them!

Pink and Carey Hart

Marriage is a tough job, especially if you're a celebrity. Pink and her motocross hubby Carey Hart split after two years of marriage in 2008, though they didn't divorce. In 2009, they began dating again. Hart even appeared in Pink's music video for So What in 2011.

That same year they welcomed daughter Willow in 2011. In 2016, Pink gave birth to a second child, a son named Jameson. When asked about the songs inspired by him, Hart revealed, “Yeah, it’s very accurate. You know, we’ve been together 21 years. I have very thick skin.”

Adam Levine and Behati Prinsloo

Adam Levine wasn't too sure that Victoria's Secret model Behati Prinsloo was the one until he dumped her and began dating fellow Victoria's Secret model Nina Agdal. Once reunited, Levine proposed. "I still don't necessarily think you have to get married unless you meet someone that makes you want to marry them. And then you marry them and it's wonderful," he said.

The couple tied the knot in 2014 and welcomed three children throughout the rest of the 2010s. In 2022, the couple suffered another blip after Levine had been caught worshipping another woman's butt on Instagram. Definitely weird, but not enough to cause a permanent relationship rupture, apparently.

Kroy Biermann and Kim Zolciak-Biermann

The Real Housewives of Atlanta's Kim Zolciak-Biermann filed for divorce from ex NFL player Kroy Biermann after eleven years of marriage. The two spent a lot of time sniping at each other in the press following the split, to the shock of absolutely no-one.

Two months after the divorce announcement, the two announced they had called it off. Biermann’s attorney, Marlys A. Bergstrom, told E! News at the time that “the parties are dismissing their divorce action and attempting a reconciliation.” Good for them... maybe?

Ashanti and Nelly

Yep. Early 2000s RnB legends Ashanti and Nelly were an item, and for a long time if you look at the standards set in Hollywood. Between 2003 and 2013, the singers had a bumpy relationship, often breaking up on a whim only to reconcile and try it again.

They reunited hopefully for the final time recently. “Nelly and Ashanti are back together and both of them are very happy,” a source told Entertainment Tonight. “Nelly and Ashanti are really enjoying their time together.” That's a pretty robotic statement for what should be a joyful reunion.

Elon Musk and Talulah Riley

Elon Musk has always seemed way more focused on trying to land a rocket on Mars and turn Twitter into a cesspit than trying to cultivate a lengthy relationship. He and Talulah Riley not only broke up multiple times but got married multiple times, too.

They started dating in 2008, marrying soon after in 2010 at Dornoch Cathedral in Scotland. They divorced in March 2012 and remarried each other less than 18 months later. On New Year’s Eve 2014, Elon celebrated by filing for divorce from Talulah again only to withdraw. However, the pair divorced again in 2016.

Rachel Bilson and Hayden Christensen

Hayden Christensen enjoyed an on-again, off-again relationship with his Star Wars co-star Natalie Portman before meeting Rachel Bilson on the set of Jumper back in 2007. The pair hit it off immediately and entered a private yet turbulent relationship.

Bilson and Christensen became engage but called it off in 2010. However, they got back together later that same year. In November 2014, they welcomed a daughter named Briar Rose but it wasn't enough to keep them together. They split again in 2017 and are yet to reconcile.

Hilary Duff and Matthew Koma

Hilary Duff, like most Disney teens, had a headline-grabbing relationship that transitioned her from her child actor era to her adult celebrity life. In 2003, she and Aaron Carter called it quits for the last time. Years later, in 2015, she moved on to Matthew Koma.

The two had met while collaborating on one of Duff's albums. They split up briefly in 2017 before reconciling the same year. In October 2018, they welcomed a daughter into the world, Banks Violet Bair. In May 2019, they became engaged and in December of that year were married.

Justin and Hailey Bieber

Justin Bieber was actually introduced to Hailey Baldwin in 2009 by her father. There's a video of it on YouTube. In the video, Baldwin doesn't seem too bothered and neither does the Beebs. And now they're married! It's weird how life works out, sometimes.

Alas, it wasn't just his relationship with Selena Gomez that has been on-and-off. In 2014, Baldwin and Bieber began attending church together. In 2016, they hooked up. Later that year, they broke it off. Bieber went back to Gomez before deciding it was Baldwin he wanted. In 2018, they reconciled and got married shortly after.

Kourtney Kardashian and Scott Disick

If you're not so big on the Kardashians and are wondering who Scott Disick is, he's the one who used to dress like Patrick Bateman and get in fights a lot. From 2006 to 2015, he was in a relationship with Kourtney Kardashian, the eldest sibling of the family.

They first broke up in 2009 amid cheating rumors, only to reconcile after discovering Kourtney was pregnant with their son, Mason. They split again in 2010 before getting back together in 2012 to have another child, their daughter Penelope. In 2016, they split up seemingly for good and are yet to reconcile.

The Weekend and Bella Hadid

Bella Hadid and The Weeknd began dating after meeting at Coachella in 2015. Soon enough, the model was appearing in his music video for In the Night. Distance, in their case however, did not make the heart grow fonder. In 2016, they decided to call it quits.

Both of their careers were skyrocketing and trying to manage a domestic situation was proving impossible. The Weekend then moved on to Selena Gomez, causing a rift between her and Hadid, who eventually won the Blinding Lights singer back in 2018. After a year of dating, the couple decided to split yet again. Bella moved on to art director Marc Kalamn, although that relationship ended in 2023.

Katy Perry and Orlando Bloom

Katy Perry took a little break from dating after her divorce from Russell Brand. In early 2016, she was spotted with Orlando Bloom, someone she brushed off as just a friend. Who paddle boards with a completely naked friend? Pop stars and actors, apparently.

At the end of 2016, the pair went their own ways, only to publicly announce their relationship was back on in 2018. Leading up to that, Bloom and Perry had been spotted at various spots. In 2019 they got engaged. A year later, they welcomed a daughter, Daisy.

Halsey and G-Eazy

Halsey and G-Eazy met at a party in 2017, developing their relationship after collaborating on the song Him & I. Throughout 2018 and 2019, the couple broke up and reconciled countless times. When Halsey accused the rapper of cheating during an SNL performance, we knew it was over.

When fans were taunting Halsey by commenting 'G-Eazy' on her Instagram posts, she replied: "I hope to God you never have to experience an abusive relationship. And if you do, I hope the world is kinder to you than you are to me." Such a statement makes it pretty clear that the pair are over for good.

Kendall Jenner and Ben Simmons

The model and NBA star were linked back in May 2018 and lasted a whole four months before calling it quits, with sources saying that Jenner just loved being with her friends and that she had no time or patience for a man in her life.

Jenner then got bored of her friends and started hooking up with Simmons again. She was even spotted hanging out with his mom at a series of Philadelphia 76ers games. By May 2019, however, the relationship was back off. No beef, apparently. They simply drifted apart.

Chris Evans and Jenny Slate

Marvel star Evans and actress and comedian Slate made their first public appearance at the New York premiere of The Secret Life of Pets in May 2016. In February 2017, however, they were reported to no longer be a couple.

The star-crossed lovers couldn't keep away from each other for too long, however, and rekindled their romance during Christmas 2017. Then again, the couple went their separate ways in March 2018, proving nobody can tie down Captain America without significant effort.

Chris Brown and Karrueche Tran

After dating Karrueche Tran for a year, Chris Brown revealed in 2012 that he wanted to be single and focus on his career. In July 2013, he and Tran were back on. Even when Brown was released from jail in June 2014, she threw the singer a welcome home party.

The relationship suffered a serious blow when Tran found out Brown had a secret daughter who was born during their relationship. Brown lashed out on social media, which Tran used to grant herself a five-year restraining order against the man in June 2017.

Wilmer Valderrama and Demi Lovato

Wilmer and Demi Lovato hooked up in 2010 but didn't address their relationship at all until 2014, when the pair started cosying up on social media. Sadly, things did not stay so cosy and in June 2016, they broke up. However, they stayed in touch. Wilmer attended Demi's birthday party the following year.

By February 2018, they were seen making out in public but the relationship remained off. When Lovato suffered an accidental overdose in July 2018, he visited her in the hospital. In April 2020, Demi revealed to Harper's Bazaar that she wishes him "nothing but the best."

Elon Musk and Grimes

In 2018, Grimes and Musk began a relationship after bonding over a shared pun on Twitter. In 2020, she gave birth to their robot son. A year later, a surrogate gave birth to their robot daughter. Grimes and Musk separated the same year.

In January 2022, Grimes described her relationship with Musk: "I would probably refer to him as my boyfriend, but we're very fluid." In March of that year, she called him her "best friend and the love of my life". In September 2023, it was reported that the couple had another (likely robot) son, though on September 29th, Grimes sued Musk over parental rights.