The Rockiest Relationships in Reality Television History

Long before Caitlyn was a socialite-turned-political candidate, she was best-known as an Olympic gold medal-winning decathlete. The two were married for 25 years before announcing their split in 2013 and officially divorcing on Keeping Up With the Kardashians by 2015. According to Caitlyn’s memoir titled The Secrets of My Life, Kris was aware that she wanted to transition genders. They share daughters Kendall and Kylie together, and today, their relationship seems amicable.

Throughout the first few seasons of Southern Charm, Thomas Ravenel and Kathryn Dennis were on-again, off-again, as they had two children on the show, but were often seen fighting in public. When they eventually split in 2016, Ravenel accused Dennis of abusing drugs, and he won custody over their children. It wasn’t long before Ravenel started dating Ashley Jacobs in season 5, who constantly picked fights with Dennis. Their relationship was also rocky and they split in August 2018 after Ravenel was charged with third-degree assault and battery of his children's former nanny. In the meantime, however, Ravenel and Dennis rekindled a friendly relationship and adjusted the custody of their children to be fifty-fifty.

Stassi Schroeder and Jax Taylor dated in 2012 when filming the first season of Vanderpump Rules, but broke up shortly after. Taylor accused Schroeder of holding him back in his career, but he also allegedly cheated on her, causing many ups and downs for them. It was a sad break-up, as Schroeder claims she spent most of the relationship waiting for him to grow up but ended up losing her best friend.

Bachelor Nation surely remembers these two. Originally engaged to Andi Dorfman in the Bachelorette finale from July 2014, Josh Murray eventually split with her in January 2015 and got engaged to Amanda Stanton on season 3 of Bachelor in Paradise in August 2016. After four months, these two broke up and got back together several times before eventually splitting up for good.

After meeting in 2006, Scott Disick and Kourtney Kardashian had a lot of ups and downs before officially calling it quits in 2015. Most of their relationship was documented on Keeping Up With the Kardashians, including the births of their three children (Mason, Penelope, and Reign), Disick’s time spent with ex-girlfriend Chloe Bartoli which led to his split with Kardashian, and his struggles with alcoholism.

However, these two now seemed to be a closed case, as they’ve both happily moved on; Kardashian is in a relationship with Travis Barker and Disick is dating model Amelia Hamlin.

Speaking of Barker, he wasn’t always hanging out at UFC fights with Kourtney Kardashian. About 16 years ago, he was married to Shanna Moakler on MTV’s Meet the Barkers, whom he stayed with until 2008 amidst cheating accusations on Barker’s part. The two constantly were fighting and making up, but had two children, Landon and Alabama, together.

When Barker started dating Kardashian in late 2020, Moakler accused the two of having an affair in the earlier 2000s, though these allegations have been denied.

This relationship was a roller coaster from start to finish. On Colton Underwood’s season of The Bachelor in 2019, he convinced Cassie Randolph to leave early with him just a few weeks before the finale. He even jumped a fence for her.

They stayed together after the finale aired but called in quits in May 2020, before Randolph filed a restraining order against Underwood claiming that he was stalking her and had put a tracking device on her car. However, the order is now dropped.

Underwood came out as gay in April 2021 and apologized to Randolph for how their relationship ended.  

Blac Chyna and Rob Kardashian dated from January to December 2016, and their ups and downs were depicted on E!’s Rob & Chyna. While they share a daughter, Dream, who they’ve fought for custody over through several lawsuits, they have also both claimed that the other has been emotionally and physically abusive.

Ronnie Ortiz-Magro and Sammi Giancola are notorious for having one of the roughest relationships in reality television history, shown on Jersey Shore from 2009 to 2012. Ortiz-Magro cheated several times, including in 2014, and the two split for the final time. In a 2018 revival titled Jersey Shore: Family Vacation, Ortiz-Magro brought his girlfriend, Jen Harley, to the house. While she was seven months pregnant, he was seen grinding on another girl at a club, then brought the girl home, which led to a physical fight on Instagram Live between Harley and him, and their eventual split in October 2019.

Kanye West’s divorce from Kim Kardashian is dull in comparison to this story. NBA star Kris Humphries got engaged to Kardashian in May 2011, seven months after their first meeting. Their marriage, beginning in August, complete with a Keeping Up With the Kardashians wedding special, lasted just 72 days. Kardashian filed for divorce after Humphries filed for an annulment, saying their marriage was based on “fraud,” but they didn’t officially divorce until April 2013.

Despite a relationship spanning many issues, from domestic violence to substance abuse to affairs, these two are still together. The Osbournes have been married since 1982 and are very open with the public about their issues, especially on MTV’s The Osbournes, their reality show in the early 2000s that showcased their home life.

Heidi Montag and Spencer Pratt have been married since 2008 and share their son, Gunner Stone, together, but it took them a while to get to a stable place. The two so-declared villains on MTV’s The Hills met on the show in 2006, as Montag was Lauren Conrad’s roommate. Between Pratt starting a sex tape rumor about Conrad to Montag faking a pregnancy, these two eventually progressed to go on Marriage Boot Camp in 2015 to work on their issues. Now, the two have reprised their original reality TV days and star on The Hills: New Beginnings.

The Jon & Kate Plus 8 stars were together for a decade before divorcing in June 2009. While they constantly fought on the show, there were also cheating rumors tossed around, connecting Kate with her bodyguard and Jon to several other women. Additionally, there have been abuse claims between the two. By October 2009, the show’s name was changed to Kate Plus 8.

The most recent of these rocky relationships, Clare Crawley was originally on Juan Pablo Galavis’s season of The Bachelor in 2014. Cast as last season’s Bachelorette, Crawley fell for contestant Dale Moss fast and hard and even quit the show a few weeks in to leave with him before Tayshia Adams stepped in as the new lead. Although the two got engaged upon leaving, they broke up and got back together several times over the following months. However, as of early July, the two were back together and engaged once again.