The Worst Celeb Relationship Reconciliations

Former Glee star Naya Rivera married Ryan Dorsey in summer 2014 on the same day she was slated to tie the knot with her rapper ex Big Sean. That may have been a pretty bad omen: Rivera filed for divorce from Dorsey, with whom she shares 2-year-old son Josey, in November 2016. By October 2017, however, Rivera withdrew her divorce petition. The reconciliation wouldn't last: Just a month later in November 2017, Rivera was arrested for domestic battery for allegedly hitting Dorsey with a cellphone on the head and lip. Less than two weeks later, TMZ reported that she re-filed for divorce, citing the ever-reliable "irreconcilable differences."

Ben Affleck and Jennifer Garner were married for a decade when they shocked the world and announced their separation in July 2015.

Us Weekly reported that shortly after he and Garner separated, Affleck was spotted with their nanny, Christine Ouzounian. Still, it appeared Garner may have considered taking him back because a year later, they still hadn't filed for divorce. In June 2016, a friend of Garner's told Us Weekly, "A lot of the damage in their relationship has been mended ... Jen would get back with him." Sources also old People in July 2016, "They're still figuring things out. Ben doesn't want the divorce and he might actually get his way."

The biggest hope for a reunion came in March 2017, when a source told People, "Jen has called off the divorce. She really wants to work things out with Ben. They are giving things another try." Another insider told the magazine, "There is always a chance of reconciliation. They love each other ... There seems to be hope."

So much for that: A month later, in April 2017, Affleck and Garner filed for divorce. A reason for that? Well, Garner may have discovered his relationship with his current girlfriend, Saturday Night Live producer Lindsay Shookus. Though they only went public in summer 2017, sources told People that Affleck and Shookus had actually been having an affair since 2013, before he and Garner even separated.

Rihanna and Drake's relationship was dizzying. RiRi and Drizzy gave it a go for the first time in 2009 when she and Brown had split, but she told Hot 97 that the timing wasn't right for them, explaining, "It was at a really fragile time in my life, so I just didn't want to get too serious with anything or anyone at that time." Drake, meanwhile, lamented to The New York Times, "She was doing exactly what I've done to so many women throughout my life, which is show them quality time, then disappear. I was like, 'Wow, this feels terrible.'"

They were linked again in 2011 when they got close performing their collaboration "What's My Name," and again in April 2012 when promoting his hit "Take Care," but nothing seemed to stick. Drake told Ellen DeGeneres in April 2013 that he and Rihanna "had their moment," but that it was over ... then called her his "ultimate fantasy" in a February 2014 interview with Rolling Stone. In March 2014, they vacationed together, but that didn't mean it was serious: In a February 2015 Vanity Fair interview, Rihanna said Brown was her "last real, official boyfriend."

By June 2016, sources told People that they were officially together, and by August 2016, Drake professed his love for Rih at the MTV Video Music Awards (and on a billboard). They got matching tattoos a month later, but by October 2016, sources told People they were in an open relationship ... and by December 2016, Drake moved on with J.Lo.

Sean Penn and Robin Wright first began dating in 1989 and tied the knot in 1996, but their relationship wasn't a smooth one. After 11 years of marriage and two children together, Penn and Wright filed for divorce in December 2007, only to call off the split four months later — but not before Penn stepped out with supermodel Petra Nemcova publicly. People reported that in April 2009, Penn filed to legally separate from Wright again, just months after noticeably omitting her from his Best Actor Oscar acceptance speech. A month later, however, the separation was called off again. Months later in August 2009, Wright was done with Penn for good, filing for divorce and telling More magazine (via People), "I hit that crossroad a while ago. I know what I don't want."

The divorce was finalized in 2010. In 2012, perhaps to add insult to injury, Penn told Esquire, "There is no shame in saying that we all want to be loved by someone. As I look back over my life in romance, I don't feel I've ever had that ... I have been the only one that was unaware of the fraud in a few of these circumstances blindly ... When you get divorced, all the truths that come out, you sit there and you go, 'What the f**k was I doing? What was I doing believing that this person was invested in this way?' Which is a fantastically strong humiliation in the best sense."

In 2015, Pamela Anderson told People that Tommy Lee, to whom she was married from 1995 to 1998 and with whom she shares sons Dylan and Brandon, was the love of her life. "There was Tommy and then there was nobody else," she said. "He was the love of my life. We had a wild and crazy beginnings that was too much for both of us. It really was love at first sight. I only knew him four days before I married him."

Not surprisingly, that wasn't the strongest foundation for a lasting marriage: The couple filed for divorce just three years later, which Lee explicitly described to Rolling Stone as being the result of moving too fast, booze, paparazzi, having a sex tape go viral before they were a thing, and domestic violence issues (including Lee's four-month incarceration following a physical fight with Anderson).

Despite the divorce, the volatile couple reunited more than once, including once in 2008, a decade after their split, when Lee told Rolling Stone (via People), "We've only given it a try 800 times – 801, here we go." It didn't last, but it didn't get as ugly as it did previously.

"I had beautiful children with him," Anderson told People in 2015 of her relationship with Lee. "My kids are grateful to be born out of true love. Everything else I was trying to piece together ... We're good friends, we're getting better at co-parenting our kids ... There's a connection there that will always be."

Pamela Anderson is nothing if not consistent: She and third husband, Rick Salomon — of One Night In Paris (2004) fame — split and reconciled multiple times. They first married in October 2007, only to annul the union just two months later that December, TMZ reported. By October 2013, however, they rekindled the flame, with Anderson telling Ellen DeGeneres that she and Salomon were "best friends with benefits." By January 2014, Anderson and Salomon had tied the knot for a second time, but six months later, Anderson filed for divorce — but just a month later, in August 2014, had her divorce petition dismissed. By February 2015, Anderson filed for divorce from Salomon for the final time, even obtaining a restraining order against him.

Kourtney Kardashian and Scott Disick began dating in 2007 and split for the first time in 2009 while Kardashian was pregnant with their first child, son Mason; they reconciled just before Mason was born that December. By 2010, Kardashian grew frustrated with Disick's drinking and dumped him, but they reconciled, and he in proposed in 2011 — which she turned down, though they stayed together. In December 2012, they welcomed daughter Penelope.

It wasn't smooth sailing post-Penelope: In June 2014, Kardashian kicked a spiraling Disick out of their home while vacationing in the Hamptons; a month later he was hospitalized after a night of heavy drinking. In a September 2014 episode of Keeping Up With The Kardashians, Disick was clearly unhappy that Kardashian was pregnant for a third time, telling her, "You keep suckering me into these kids ... I can't handle all this responsibility." Reign was born in December 2014, and the Disick and Kardashian rang in January 2015 together.

By March 2015, Disick went to rehab, and he and Kardashian were going strong until July 2015, when he was photographed getting cozy with stylist Chloe Bartoli while vacationing without Kardashian. Since then, the pair have remained apart, with Kardashian dating model Younes Bendjima and Disick being linked to a bevy of much younger women, including Bella Thorne and Sofia Richie — though sources told People he's doing it all in hopes of making Kardashian jealous enough to take him back.

Rob Kardashian and Blac Chyna were basically the definition of toxic: Their relationship was riddled with infidelity accusations, a Kardashian family feud, a quickie pregnancy, a broken engagement, a daughter named Dream, and a reality show. They split and reunited at least twice that the world knows of, first in July 2016 (after which they immediately reconciled), then in December 2016, though they were back together by their anniversary on Jan. 25,2017. However, the dramatic romance was over for what seemed like for good by mid-February 2017 — though the drama, in the form of revenge porn, social media pettiness, and lawsuits, is ongoing.