On-Again, Off-Again Celebrity Couples

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Some couples just need a break every now and then! Click through to see which of your favorite celebrity couples — like Jessica Biel and Justin Timberlake — couldn’t help splitting and rekindling year after year.

Awwww: Celebrity Couples With The Most Romantic Love Stories!

On Again, Off Again Celebrity Couples

Some couples just need a break every now and then! Click through to see which of your favorites couples — like Jessica Biel and Justin Timberlake — couldn’t help splitting and rekindling year after year.

Jeffrey Mayer/WireImage; Steve Granitz/WireImage; Lester Cohen/Getty Images for Sony Music Entertainment; Kevin Mazur/Getty Images

Kendall Jenner and Ben Simmons

The model and the NBA star were first linked in May 2018. Four months later, the first signs of trouble kicked in, with a source confirming to Us Weekly that the pair called it quits. “Kendall just loves being with her friends. That’s her main priority right now,” the insider told Us at the time. In the months after their initial breakup, the pair started “hooking up” again. The Keeping Up With the Kardashians star was even spotted hanging out with the pro athlete’s mom at a handful of Philadelphia 76ers games. Alas, come May 2019, the former couple split again. “Things have wound down between them,” said another insider. “They aren’t seeing each other anymore.”

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Ronnie Ortiz-Magro and Jen Harley

The Jersey Shore star and his girlfriend have had several ups and downs since they began dating in July 2017. Weeks after welcoming daughter Ariana in April 2018, they exchanged insults in since-deleted Instagram Story videos. In June, the pair got into a physical altercation while the MTV cast filmed season 2 of Jersey Shore: Family Vacation in Las Vegas. The following month, however, the pair appeared to be back together as they celebrated the Fourth of July with their family. 

Courtesy of Jen Harley/Instagram

Halsey and G-Eazy

The “Bad at Love” singer and the “No Limit” rapper sparked romance rumors in the summer of 2017 following his split from Lana del Rey. They made things Instagram official in September of that year, but after nine months of dating, the duo called it quits. Halsey confirmed the news to fans with an Instagram Story posted on July 3. “I normally keep this kind of thing private but provided our public nature I feel the need to inform my fans. G-Eazy and I are taking some time apart,” she wrote. One month later, the pair rekindled their romance at an afterparty for the 2018 MTV Video Music Awards, with a source revealing to Us in September that they were “figuring things out.” “They aren’t trying to hide the fact that their relationship is complicated,” the source shared, adding, “They were so serious before and now they don’t feel that same pressure to define it.”

 

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Justin Bieber and Hailey Baldwin

Baldwin adored Bieber way before she met him — she was a huge Belieber before the pair started dating in 2015, evidenced by tweets from over the years. In January 2016, the pair brought in the New Year together in Anguilla, with the model sharing a black-and-white photo of her arms around the “Friends” crooner while the singer shared his own steamy photo of them kissing. After Baldwin asked Bieber to settle down with her, the “Love Yourself” singer called her “someone I really love” in an interview with GQ in February 2016. They later went their separate ways, with Bieber spending time with Kourtney Kardashian and Baldwin being linked to Drake and Shawn Mendes . While the pair were “off,” Bieber briefly reunited with ex-girlfriend Selena Gomez until they broke up for good in March 2018. Us exclusively revealed that Baldwin and the “Sorry” singer were hooking up again in June 2018 when they were spotted hanging out in Miami — and a few weeks later, Bieber proposed in the Bahamas.

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Katy Perry and Orlando Bloom

These two just can’t quit each other! The “Swish, Swish” singer and Bloom first dated in 2016 for 10 months before calling it quits in 2017 — but not for long. After their breakup, they were spotted quietly hanging out in London in May 2017. Since then, they’ve been seen spending quality time together on several occasions and in February 2018, Us exclusively revealed they were hooking up again. In May 2018, Perry hinted that the two were official, saying she was “spoken for” during an interview with Entertainment Tonight

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Megan Fox and Brian Austin Green

Being known as one of the sexiest couples in Hollywood doesn’t always guarantee both parties are at their happiest. In August 2015, after 11 years together, five years of marriage and welcoming two sons, Noah and Bodhi, Fox filed for divorce from Green. However, the 90210 alum wasn’t willing to go without a fight and he whisked the Transformers actress on a romantic vacation to Hawaii — the same place where they got married in 2010. Us exclusively revealed that the pair had reconciled and during that time, Fox got pregnant with their third child, Journey. In March 2018, the Jennifer’s Body star told Us that getting quality time together was essential to their relationship so “you remember why you like the person that you had kids with.” 

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Chris Evans and Jenny Slate

The Avengers star and Slate made their first public appearance as a couple at the New York premiere of The Secret Life of Pets in May 2016. However, Us exclusively revealed they were no longer together in February 2017. The former flames started hanging out again during the holiday season that year but in March 2018, the New York Times revealed during a profile of Evans that the pair had broken up once again. 

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Selena Gomez and Justin Bieber

These two love birds call it quits so often it’s honestly almost impossible to keep track. Bieber and Gomez were first linked together in December 2010 but didn’t make their official public debut until February 2011. The couple’s endless series of splits began in November 2012 and continued until 2015. Us exclusively revealed that the “Love Yourself” singer and Gomez had gotten back together once again in November 2017 and their brief rekindled romance saw the pair going on various romantic getaways. They later ended things in March 2018 and sources told Us at the time that the split was “mainly because of Selena’s mom and her disapproval of Justin.” While Gomez and Bieber may have gotten back together over the years, this time was likely their last — Bieber proposed to Hailey Baldwin in July 2018, writing on Instagram, “You are the love of my life Hailey Baldwin and I wouldn’t want to spend it with anybody else.”

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Audrina Patridge and Corey Bohan

After dating on and off for five years, the couple ended their relationship in July 2014. In October that same year, the former Hills star was spotted out with the BMXer at a Halloween party and the two appeared to be back on. The reality star and Bohan married in an intimate Hawaii wedding in November 2016 after welcoming daughter Kirra, who was born in June 2016. Despite trying to make things work, Patridge filed for divorce on September 20, 2018, and was granted a temporary restraining order a week later. After accusing the BMX rider of aggressive behavior and citing various alleged domestic violence incidents, she went back to another former boyfriend: Ryan Cabrera

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Chris Brown and Karrueche Tran

After dating for a year, Brown told Us in 2012 that he wanted to be single and focus on his career. Fast-forward to July 2013 and the couple appeared to be back on, stepping out together numerous times and sharing lovey-dovey Instagrams with one another. Following the end of Brown’s jail time in June 2014, the stylist threw the rapper a welcome home party. Their rocky relationship ended for good after Tran found out that Brown had a secret daughter who was born during their relationship — and the rapper didn’t go away quietly, sharing disturbing and threatening videos on social media in February 2017. Tran was later granted a five-year restraining order against Brown in June 2017. The rapper later extended an olive branch on March 24, 2018, when he commented “They look really good together” with a praying emoji on a photo of Tran and her boyfriend, Victor Cruz.

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Prince Harry and Cressida Bonas

Prince Harry and Cressida Bonas met through Harry’s cousin Princess Eugenie and dated for two years before calling it quits in April 2014. Following their split, however, the two were spotted together in September. A source told Us of the prince and Bonas: “Harry is the type to want to take breathers and then try again.” The royal eventually married Duchess Markle in a highly publicized wedding on May 19, 2018, at St. George’s Chapel in London. However, there were no hard feelings between Prince Harry and Bonas — the model even attended the nuptials.

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Justin Timberlake and Jessica Biel

Timberlake and Biel took a three month break in 2011 only to reunite with one another and get married in October 2012. “When they reunited, they had a conversation about taking the next step,” a source told Us at the time of their engagement. Us revealed the couple, who dated on and off for five years prior to their engagement, were expecting their first child in November 2014.

Kevin Mazur/Getty Images for GQ

John Mayer and Katy Perry

These two just couldn’t make up their mind until officially splitting in 2014. Perry started dating Mayer following her divorce from Russell Brand in the summer of 2012. The two called things off that fall, only to rekindle their romance and then split again in March 2013. After reuniting a final time in June, the singers officially split in February 2014.

Lester Cohen/Getty Images for Sony Music Entertainment

Hayden Christensen and Rachel Bilson

Now parents to a daughter, Christensen and Bilson spent time apart from each other during their on again, off again relationship. The couple met in 2007 on set of Jumper and got engaged in December 2008, only to call it off in August 2010. Three months later, however, the couple were back on!

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Sienna Miller and Jude Law

On and off for three years, Jude Law and Sienna Miller put an end to their roller-coaster romance in 2006, after calling it quits on their engagement in 2004 following Law’s affair with his children’s nanny. The Factory Girl star later married Tom Sturridge — with whom she shares daughter Marlow — before they filed for divorce after four years together in July 2015. In 2016, Miller — who was later linked to Brad Pitt in 2017 — said of Law, “I care about him enormously.”

Larry Busacca/Getty Images North America

Demi Lovato and Wilmer Valderrama

Together since 2010, Lovato has remained coy about her relationship with Valderrama. However, beginning in 2014, the couple started to publicly address one another on Twitter and in Instagram photos. The “Sorry Not Sorry” singer and Valderrama split in June 2016 after six years of dating, but they remained friendly. In August 2017, Lovato celebrated her 25th birthday alongside the That 70’s Show star. The former couple were later spotted showing major PDA during a lunch date in February 2018, where an eyewitness revealed they had their arms around each other.  

 

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