18 On-Again, Off-Again Celebrity Couples, Ranked By Success

The jury is still out on whether on-again, off-again relationships work. On the one hand, you’re exes for a reason. On the other hand, if you love something let it free… if it comes back, it’s yours.

Whether or not it’s ultimately a healthy relationship move, plenty of celebrity couples are notorious for breaking up, making up, and keeping us guessing about the status of their relationship by going on-again and off-again like it’s their freakin’ job (and depending on who you ask for a celebrity, it kind of is). Some couples end in scandal and should probably stay ended. Some were just too good to be true, but we still wish they’d find each other again. And some of the best celebrity “couples” are the ones whose friendships are #goals.

One thing is for sure, and that’s that some on-again, off-again couples are more successful than others (you’ve heard about the reunion of Jelena, right?). Here are 18 of those celebrity couples known for the ever-changing state of their relationship status, ranked from least to most successful.

18. Rihanna and Chris Brown

I wish I didn’t have to include this relationship on this list because I wish Rihanna never went back to Chris Brown after what he did, make a song with him, and then finally leave him for good (let’s hope). I wish even more that Chris Brown had just never done what he did. But in lieu of that, I’ll remind everyone that Chris Brown is the perpetrator of multiple domestic assaults and there is no reason that we should still be listening to music that he is somehow still popular enough to make.

Success rating: 0 / 5

17. Rob Kardashian and Blac Chyna

Rob Kardashian and Blac Chyna actually take the fun out of dysfunctional. Nothing is fun about allegations of physical abuse or posting revealing photos without consent for revenge. Neither is emptying a nursery and leaving with your partner’s child without consulting with him first. Rob and Blac Chyna both seem like extremely unstable human beings, and they’re actually better off (Dream included) when they’re not in a relationship. Plus, the fact that Rob’s girlfriend has a baby with his half-sister’s boyfriend (see #3) was always way too weird, even for that family.

Success rating: 0.5 / 5

16. Tyga and Kylie Jenner

But seriously, what kind of teenager is like, “yes, I enjoy dating the baby daddy of my much older half-brother’s girlfriend/baby mama”? Tyga and Kylie’s relationship is interesting, to say the least. She first appeared interested in him when she was a mere 14 years old — Tyga is seven years older and was dating Blac Chyna, who he was engaged to while she was pregnant, though they broke it off before the wedding. Kylie and Tyga were “friends” for years and rumors flew about the nature of their relationship (including during a cheating allegation against Tyga), but nothing was confirmed until Kylie turned 18. They date, break up, date, break up… through not one but two brand new cars from Tyga. And now, Kylie has had a baby with her boyfriend Travis Scott. Will this keep Tyga away for good?

Success rating: 1 / 5

15. Kate Hudson and Owen Wilson

These two blonde babes just couldn’t make it stick. Kate Hudson and Owen Wilson got together after meeting on the set of You, Me, and Dupree and Kate split with husband Chris Robinson. After their first breakup, Owen struggled with mental health issues and attempted suicide in 2007, some say after hearing Kate was dating Dax Shephard. They briefly rekindled their romance but split again before reaching the two-month mark. Fortunately, Owen has been doing much better in the past decade.

Success rating: 1.5 / 5

14. Sammi Giancola and Ronnie Ortiz-Magro

For those of us who indulged in Jersey Shore as a guilty pleasure (no judgment), we saw how dramatic Sammi “Sweetheart” Giancola and Ronnie Ortiz-Magro were over the years. Instead of Gym, Tan, Laundry, their routine was fight, break up, get (back) together later. It was amazing they stayed together at all after the show ended, but it didn’t last — neither did their post-show breakup, as they got back together over a year later. Alas, there was no hope for their sequel and according to Instagram, Sammi is very happy with her current boyfriend. But the two really made a go of it for nearly eight years.

Success rating: 2 / 5

13. Jennifer Lawrence and Nicholas Hoult

Jennifer Lawrence and Nicholas Hoult always seemed like a staged couple to me. Two young, attractive actors kicking off their careers who happen to be working together on the set of a movie series — it’s too perfect not to be a setup. The couple dated for a few years, broke up, and then got back together again just in time for another X-Men installment. How convenient for getting people excited about the latest movie! I actually rank this couple as more successful than some because even though it didn’t seem like a genuine romance, it seemed like a pretty good business partnership.

Success rating: 2 / 5

12. John Mayer and Katy Perry

After her divorce from Russell Brand — which was initiated when he sent a text to end their relationship — Katy Perry was linked with John Mayer. The two were a relatively coy couple, playing cat and mouse with the media and appearing to get together and break up several times over the course of a few years, during which they released the romantic ballad “Who You Love.” As they say, you love who you love, and apparently, they didn’t love each other enough. They may not have ultimately ended up together, but they left a pretty decent musical legacy behind.

Success rating: 2 / 5

11. Eminem and Kim Mathers

Eminem and ex-wife (times two) Kim Mathers usher us into a new category: formerly married and with kids. Marshall Mathers actually married his high school sweetheart and mother of his daughter Hailie. The couple divorced after two years but tied the knot again about five years later. The second time around was even less successful, as they divorced again after just a few months. But the couple did manage to get betrothed (twice!) and raise children together, so they’re on the more successful end of the spectrum.

Success rating: 2.5 / 5

10. Wiz Khalifa and Amber Rose

Amber Rose is open to admitting that she and ex-husband Wiz Khalifa rushed into marriage and that they’d probably still be together if they had waited longer before walking down the aisle — and there’s plenty of speculation that they have gotten back together at times, though they claim just to be friends. The currently off-again couple have a son together, who Amber Rose was quick to defend when ex-boyfriend Kanye West tried to start beef on social media with Wiz Khalifa.

Success rating: 2.5 / 5

9. Rachel Bilson and Hayden Christensen

After meeting on set, Rachel Bilson and Hayden Christensen started a romantic relationship. The couple actually got engaged after under two years, but the wedding was called off before a save the date was sent out. After just a few months apart the couple got back together for seven years and had a daughter together. Unfortunately, the pair has just recently broken up again. Sources are saying it’s officially over this time, but it’s really too early to tell. Honestly, we’ll see how that goes… maybe they’ll end up resurrecting that long overdue wedding.

Success rating: 3 / 5

8. Kourtney Kardashian and Scott Disick

No, Kourtney Kardashian and Scott Disick were never officially married, but the off-again couple does have three children together and seem to manage co-parenting with relative aplomb. Even though Lord Disick is often reprimanded for his partying and tendency to hang out with young models, he’s a good father, and he and Kourtney make their unique relationship work for their family. There are rumors that Kourtney is pregnant again, this time by current boyfriend Younes Bendjima. Tbh, I am still hopeful that Kourtney and Scott will walk down the aisle together one day, accompanied by a wedding party made of their children.

Success rating: 3 / 5

7. Justin Bieber and Selena Gomez

And now, we have the on-again, off-again couples. Jelena is back in full force and I am HERE FOR IT. Justin Bieber and Selena Gomez were so young when they first got together, and their hormones + escalating stardom was a lot for any relationship, causing them to break up, make up, and keep everyone on their toes.

After years apart filled with various relationships, hit songs, questionable mishaps (on Bieber’s part), and a sobering Lupus diagnosis (on Selena’s part), the couple were back together. That was until Justin met Hailey Baldwin and it was all over.

Success rating: 3.5 / 5

6. Miley Cyrus and Liam Hemsworth

Yet another case of being just too young — Miley wasn’t quite 20 years old when she got engaged to Liam Hemsworth, a relationship that had already had ups and downs with breakups and makeups over the course of a couple years. A year later, the engagement was off. Miley went a little crazy with her now-infamous VMAs performance and tongue wagging antics, and Liam kind of fell back into the shadows. Fast forward to now, and the rock is back on Miley’s finger… in fact, more recent rumors state that the two might already be married! She does seem to have done some growing up in the past few years and calmed down a lot. The two seem to balance one another out.

Success rating: 4 / 5

5. Ross and Rachel (had to)

I know these are fictional characters, but Ross Geller and Rachel Green of Friends are the epitome of an on-again, off-again couple. The entire series followed a plot line of “will they or won’t they,” including a Vegas marriage and a surprise pregnancy. Just when you thought they were splitting up for good and Rachel was moving to another country, Ross declares his undying love, and Rachel… gets off the plane. (Sorry if that was a spoiler alert, but the series ended 13 years ago. Now I want to rewatch it on Netflix.)

Success rating: 4.5 / 5

4. Justin Timberlake and Jessica Biel

Triple threat Justin Timberlake and talented actress Jessica Biel dated for four years before a supposedly amicable breakup. Throughout the duration of the split, which lasted less than a year, the couple was spotted out and about together on numerous occasions. When they officially got back together, they got engaged and had their first child less than a year after the wedding. Though divorce rumors have swirled, the couple has never confirmed experiencing marital problems that are taking them in that direction.

Success rating: 4.6 / 5

3. Adam Levine and Behati Prinsloo

Adam Levine has a very specific type, and that type is model. Just two months after breaking up with model Anne Vyalitsyna, Levine was linked to model Behati Prinsloo. After less than a year, the couple broke up, and Levine rebounded with model Nina Agdal. That was short-lived, and Levine and Behati made up, quickly getting engaged and and married. The dangerously beautiful couple is now married with a daughter and another child on the way, proving that there might be hope for on-again, off-again couples after all.

Success rating: 4.7 / 5

2. Pink and Carey Hart

After navigating four years of dating, through ups and downs and in-betweens, Pink actually proposed to Carey Hart, and they were married for two years. They then experienced a split that they were adamant had nothing to do with cheating or scandal or love lost of any kind. Divorce papers were drawn up, but never signed, and the couple returned to each other less than a year later when she asked him to be in the music video for “So What,” a song she wrote about their breakup. They now have two children together, a daughter and a son, and have been married for 11 years.

Success rating: 4.8 / 5

1. Prince William and Kate Middleton

It might be hard to believe, but Kate Middleton might never have become the Duchess of Cambridge. The couple first got together in college, but Prince William’s family urged him to reconsider after a few years due to the pressures of life as royalty. After two years apart, the two reunited, and Prince William proposed a year later. The couple is now married with two children, and, you know, are part of the royal family of England, so the only way they could really get a higher success rating is if they had never broken up in the first place.

Success rating: 4.9 / 5

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