Reality Show Stars Who Have Dated Actors

Once upon a time, any relationship overlap between the reality TV and acting realms seemed highly improbable. There were A-listers who let it be known that they regarded reality show stars with scorn, with "The Keeping Up With the Kardashians" clan being a popular target of their derision. "My dog has more dignity than those f***ers," Oscar winner Gary Oldman once told the Independent. The Kardashians also made "Mad Men" actor Jon Hamm want to curse. "Whether it's Paris Hilton or Kim Kardashian or whoever, stupidity is certainly celebrated. Being a f***ing idiot is a valuable commodity in this culture," he told Elle UK in 2012 (via Daily Mail).

But eventually, Hollywood began warming to reality TV. "The Real World: San Diego" cast member Jamie Chung is an early example of a reality star who transitioned to acting successfully, landing roles in "Once Upon a Time," "Gotham," and numerous other TV series and films. Then there are the actors who made the opposite transition, with "The Real Housewives of Beverly Hills" cast members Denise Richards and Lisa Rinna being examples of entertainers who revitalized their careers by embracing reality TV.

While there will always be haters, there are also Hollywood heavyweights who have openly admitted to being obsessed with reality shows; Jennifer Lawrence told The Hollywood Reporter that she's a fan of the Kardashians and the "Real Housewives" franchise. There are even a few actors who have found love with reality stars, albeit with mixed results.

During Season 16 of "The Bachelor," Courtney Robertson played the role of the villain so perfectly that she titled her memoir "I Didn't Come Here to Make Friends: Confessions of a Reality Show Villain." Among the revelations in the book is her claim that she had an on-again, off-again relationship with "Desperate Housewives" actor Jesse Metcalfe.

According to Robertson, Metcalfe first laid eyes on her when she was withdrawing money from an ATM, and he leaped out of his car to ask for her number. However, she had to tell him that she had a boyfriend at the time. When their paths crossed again at a party in the Hollywood Hills, this wasn't the case. Robertson was so smitten with Metcalfe that she claims that she blew off "Entourage" actor Adrian Grenier to pursue a relationship with him.

Robertson's romance with Metcalfe purportedly started to sour after she found a pair of pink undies that didn't belong to her in his bed. She says that she forgave Metcalfe for that offense but decided to dump him for good when TMZ published photos of him with another woman. "After being heartbroken about Jesse for about ten minutes, I decided I wanted revenge," she writes. That revenge was joining the cast of "The Bachelor." When she gave Metcalfe a heads-up about her decision, Robertson says that the actor unhappily predicted that bachelor Ben Flajnik would pick her — and he was proven correct.

In 2023, we saw the rise of multiple seemingly random celebrity couples, including "Sk8tr Boi" singer Avril Lavigne and "Taste" rapper Tyga. Not to be outdone, Tyga's ex, "The Kardashians" star Kylie Jenner, raised eyebrows with an unexpected romance of her own. In April 2023, People reported that Jenner was casually dating "Dune" star Timothée Chalamet after meeting him in Europe — a surprising love match that would add some cachet to the Kardashian brand. Also surprising? An insider said of the rumored couple, "They have a lot to chat about." But while Jenner is best known for her obsession with selfies and cosmetics, she might be more capable of having deep conversations with an accomplished artiste like Chalamet than people would imagine. "When I think about you I think of a wise old soul," Kim Kardashian wrote of Jenner in a 2020 Instagram post. As for Chalamet, his youthful features also belie the number of years he feels like he's existed on this planet. "The perspective that feels 'old man,' I feel like I was born with it," he told British Vogue.

Like Jenner's exes Tyga and Travis Scott, Chalamet can also rap. On "The Late Late Show," the actor confessed to rapping under the stage name Lil Timmy Tim in high school. He even credits an encounter with Scott's frequent collaborator, Kid Cudi, for inspiring him to pursue a career in the arts.

In 2004, MTV showed us that there really are high schoolers out there living lavish, melodramatic lives like those portrayed in fictional soaps, namely "The O.C." The network's popular reality series "Laguna Beach" even had a love triangle: Fans were either Team Kristin Cavallari or Team Lauren Conrad in the competition for Stephen Colletti's heart. But the star would eventually leave the world of pseudo-reality behind for a real acting role in the drama "One Tree Hill." Colletti also started dating an actor: "Heroes" star Hayden Panettiere. 

The lovebirds appeared together in a 2006 episode of "Punk'd" in which Coletti was filmed dutifully waiting for his girlfriend to finish fake-baking during a visit to a tanning salon. Coletti was led to believe that maintenance workers were taking pictures of Panettiere — who was in on the prank — through a hole in the wall. But by the time Ashton Kutcher ambushed him to let him know that he'd been set up, Coletti was more concerned about getting sued for Panettiere pushing over the ladder one of the men was standing on and injuring him than he was about his girlfriend getting photographed naked.

When the couple called it quits in 2007, Panettiere told Seventeen (via E!), "I just knew I wanted to breathe. I wanted to be single at the time." But by the end of the year, People was reporting that Panettiere had moved on with her "Heroes" co-star Milo Ventimiglia.

From 2007 to 2009, Rob Kardashian dated "The Cheetah Girls" star Adrienne Bailon. He was still making regular appearances on his family's reality TV series at the time, and what viewers saw didn't always leave them with the best impression of the playboy. In a 2009 "Keeping Up With the Kardashians" episode, Kardashian came off as a lovesick puppy who was determined to win Bailon back, calling her over and over again and leaving messages on her phone. But the following year, Kardashian confessed that Bailon had dumped him for being unfaithful.

In a 2014 interview with Latina, Bailon expressed regret over appearing on her ex's show. "To be stuck with that Kardashian label, that was so hurtful to me and to my career," she said. The singer-actor further revealed that she had to deal with angry "KUWTK" fans who felt that Kardashian was the wronged party in their relationship. "It always bothered me that people were like, 'Pero, why couldn't you forgive him?' Why are women always the ones who have to forgive?" she wondered.

Bailon's Kardashian connection continued to haunt her in 2016. In an episode of "Rob & Chyna," Kardashian put an unnamed ex on blast for cheating on him. By then, Bailon had joined the cast of the talk show "The Real." She shut down any speculation that she was the ex in question by assuring viewers, "I absolutely never cheated on Rob."

In a 2022 Harper's Bazaar interview, Renée Zellweger revealed that her love story with Ant Anstead began when she saw an episode of "Celebrity IOU," a reality series hosted by "Property Brothers" stars Jonathan and Drew Scott. On the show, the handymen help celebrities renovate the homes of people who are important to them. Zellweger had seen the episode featuring Brad Pitt, and it inspired her to look into appearing on the show. She wanted to do something special for the two nurses who cared for her publicist, Nanci Ryder, before she died from ALS in 2020. 

Instead, Zellweger was invited to appear on a 2021 episode of the Discovery+ spinoff series "Celebrity IOU: Joyride." The concept is similar, but Anstead and his co-host, Cristy Lee, refurbish vehicles instead of homes. Anstead was impressed when Zellweger was willing to roll up her sleeves and scurry underneath a 1970 Ford Bronco to unscrew a bolt, and he also praised the Oscar winner for knowing how to use a grinder. 

In a 2021 interview with USA Today, Anstead quipped, "The irony of the show being called 'IOU,' it's like, 'Thanks, Discovery.' It's actually I that owe you. And I can recommend Discovery+ dating service to anybody." While Zellweger is notoriously private when it comes to her love life, she makes occasional appearances on Anstead's Instagram page, where he adorably described her as "the smoke show Ren" in a March 2022 post.

In October 2008, Page Six spoke to eyewitnesses who purportedly saw "The Hills" cast member Kristin Cavallari leaving a Miami party with "Captain America" actor Chris Evans. However, Cavallari told Us Weekly that she and the A-lister were just good buds. "I've known Chris for a while, just through mutual friends," she said. "I've known him for a few years, actually." The year prior, Cavallari was romantically involved with another actor who would later play a superhero: "What I Like About You" star Nick Zano. The lovebirds became serious enough that they started getting all domestic, with outlets publishing pics of the couple shopping for groceries together in April 2007.

Like Evans, Zano sported a star on his chest to play Captain America's similarly buff DC counterpart, Citizen Steel. But he and Cavallari had been broken up for years when he joined the cast of "Legends of Tomorrow." In January 2008, a source told E! that Cavallari was getting a tattoo of Zano's initials zapped away via laser treatments. "It is kind of painful, but she wants that thing off," the insider dished. 

Zano moved on with his "My Sexiest Year" co-star Haylie Duff, whose older sister, Hilary Duff, sang the theme song for "Laguna Beach." Cavallari, meanwhile, began fighting with Audrina Partridge over Justin Bobby Brescia on "The Hills." But on "Watch What Happens Live" (via Jezebel), Cavallari admitted that she and Brescia faked their relationship for the show.

Jake Pavelka failed to find lasting love with Vienna Girardi after giving her his final rose on Season 14 of "The Bachelor," which premiered in 2010. But the pilot extended his 15 minutes exponentially when he managed to get another high-profile romance off the ground. In 2012, Tony Award-winner Kristin Chenoweth confessed to People that she and Pavelka were seeing each other. By then, Pavelka had launched an acting career, portraying — what else? — a pilot on the soap opera "The Bold and the Beautiful." But his meet-cute with Chenoweth was straight out of a Hallmark original movie script: a seemingly sweet Southern gentleman from Texas charms a huge Hollywood star after fate brings the unlikely pair together. "We met at an awards show for Hallmark," Pavelka told Us Weekly. "She hosted and I was presenting an award." The event was likely the American Humane Association Hero Dog Awards.

But the couple didn't get a Hallmark happily ever after; by the end of 2013, Chenoweth was dating "Fifty Shades of Grey" producer Dana Brunetti. Their romance didn't last, either.

In April 2023, Chenoweth told ET that she and her musician beau of five years, Josh Bryant, were planning their wedding. As for Pavelka, in 2018, he told People that he was dating an attorney from Arkansas whom he met at the gym. "She came walking in in a red dress in high heels, and man, she is a train-stopper," he recalled.

Former journalist Carole Radziwill claimed that she once had a cerebral summer romance with "The Menu" star Ralph Fiennes. Speaking to Us Weekly in 2014, "The Real Housewives of New York" star fondly reminisced about the time they purportedly spent together in London, saying that one of their interactions served as the inspiration for a final scene in her novel, "The Widow's Guide to Sex and Dating." She recalled, "I hadn't seen Ralph for some time and heard he was in town. I left a note at his hotel." She copied one of Irish author Samuel Beckett's private letters, explaining, "I knew Ralph would get the reference. He's very intelligent, you know." According to Radziwill, she and the actor later met up at a bookstore, where Fiennes left with some reading material. "I saw him a few months ago and he said the book was on his bedside table ... He's an insatiable reader," Radziwill said.

On a 2014 episode of "RHONY," Radziwill claimed that George Clooney is also on her list of famous lovers. "We dated, literally, during the Eisenhower administration," she stated. Radziwill hinted that the main character's love interest in "The Widow's Guide" was inspired by the Oscar winner, telling The New York Times, "If you're going to create a character that all women fantasize about, it's always going to have a little Clooney in it whether you've kissed him or not."

Calum Best, the son of Northern Irish football star George Best, parlayed his nepo baby status into a reality career, appearing on "Celebrity Love Island" in 2005. But two years later, People reported that he and "Mean Girls" star Lindsay Lohan were turning Paradise Island in the Bahamas into their own love island. They were spied smooching up a storm, basking in the sun, and enjoying the nightlife. But when the pair took their lovefest to NYC days later, sources claimed that they had an explosive fight, apparently over Calum getting caught filling up his phone contacts with other girls' numbers. "Calum's clothes were torn, and after a few minutes, they got back into the elevator and went back to their room," an eyewitness stated to Page Six.

By November 2008, their romance was over. Lohan had moved on with Samantha Ronson, and Calum believed that the women were together because of him; he suggested that he had turned Lohan off of men. "Yeah, I was that bad to be fair," he told Celebrity Juice (via Digital Spy). 

Calum reflected back on his bad behavior in his memoir, "Second Best: My Dad And Me." He writes, "When we go out I flirt with other girls, sometimes in front of [Lohan], and one day she catches me hanging out with another girl in my hotel room" (via Radar). He also confesses to cheating on Lohan with an escort who filmed their sexual encounter.

Charlie Sheen's "rock star from Mars" era was far in his rearview mirror when the former "Two and a Half Men" actor met Jess Impiazzi at a condom launch event in 2016, but he looked like he was "hashtag winning" again when he posed for a photo with the British "Ex on the Beach" star. Sheen later told The Guardian that tabloids had started reporting that he and Impiazzi were dating, which was false at the time. "It's the one time I wanted the story to be true!" he said. "But I'm the f***ing AIDS guy, so what am I going to say? 'Come to the hotel and have a scone?' It's s*** city, man."

Apparently, the scone line worked, because Sheen got his wish. One month later, Impiazzi told the Daily Star that internet trolls were harassing her over her relationship with the actor, with one of their favorite methods of attack being to reference Sheen's HIV-positive status. "I have had tweets calling me a s**g and saying, 'Now you've got HIV,' And other people were calling me 'AIDS Girl,'" she recalled. However, Impiazzi didn't let her haters prevent her from having a good time with Sheen; she revealed that they had gone on a date to the Jack The Ripper museum. "In a way, his HIV diagnosis means I'll have to get to know him better before we go any further, which is a good thing," the reality star said.

Brandi Glanville's journey to becoming a Bravolebrity began when she married an actor, Eddie Cibrian, in 2001. She didn't become a tabloid fixture until Us Weekly reported that Cibrian was cheating on her with his "Northern Lights" co-star LeAnn Rimes in 2009, but according to Glanville, she had some juicy stories to share long before that saga began.

On the "Everything Iconic" podcast, Glanville claimed that she was romanced by two stars of "Friends." She said that she went home with Matt LeBlanc once, but he did something that killed the mood. "He let his dog lick his ice cream, and I was out," she stated, adding that LeBlanc kept eating the frozen treat after his pet drooled on it. "The Real Housewives of Beverly Hills" star claimed that she had a much longer relationship with David Schwimmer, who also did something that she had a difficult time getting past. "He wore concealer out during the day ... it really annoyed me," she revealed. 

On a 2012 episode of "Watch What Happens Live," Glanville said that she also hooked up with "300" actor Gerard Butler, who confirmed her claim when he appeared on "WWHL" in 2018. After visibly cringing, he revealed, "I had no idea who she was." On Twitter, Glanville admitted to not telling Butler that she was a reality star when they met but argued that it didn't matter. "If he wants to cringe now he can f*** off," she added.

According to "The Real Housewives of New York" cast member Sonja Morgan, she has something in common with "The Addams Family" star Anjelica Huston: They both dated Jack Nicholson. In a 2017 appearance on "Watch What Happens Live," Morgan claimed that she had a blast dating "The Shining" star. When host Andy Cohen asked how often they had hooked up, she replied, "One big sloppy mess whenever we could." The designer apparently understood that their relationship was unlikely to progress beyond these clandestine liaisons, saying, "Nobody nails down Nicholson." And the Oscar winner would agree. "I am an extreme person. If someone says: 'Jack, you are a womanizer,' I don't deny it," he told The Sun in 2012.

That wasn't the only time Morgan made a major revelation about her love life on "WWHL." In 2020, she told Cohen that she once dated "Curb Your Enthusiasm" star Richard Lewis. "He's a very smart man," Morgan said. "He's really intense, and you know, I like a smart guy." Morgan has claimed that her list of famous flings also includes Nicholson's "How Do You Know" co-star Owen Wilson. "I met him in New York through some art friends," she told ET in 2017. During that same interview, she confessed that she was dating a count at the time she was sneaking off to see Nicholson. "We were just being bad, you know," she said of her social circle's behavior back in the day.

In 2013, "Desperate Housewives" star Eva Longoria tried to cash in on the dating competition craze by producing the NBC series "Ready for Love." But viewers didn't fall in love with the show, which was canceled after three episodes aired. The fans it did find could watch the remainder of the series on various streaming services. During the finale, they learned that entrepreneur Ernesto Argüello's choice was Shandi Finnessy, who won the Miss USA pageant in 2004. But soon, rumors began swirling that their romance had fizzled and Argüello had moved on with Longoria. A source told E! that Argüello was staying with the actor at her home in Los Angeles. The insider also claimed that the pair had been spotted cozying up to each other while taking Longoria's convertible out for a spin. Longorio's rep denied the romance rumors, telling the outlet, "Eva is not dating Ernesto. She is friends with all of the guys and matchmakers from the show, but nothing further."

Longoria and Argüello's friendship did eventually blossom into something more, however. "We have the press to thank for pushing us to see something we didn't see," Longoria told People in July 2013. By then, Argüello had already taken the actor to Nicaragua to meet his family. 

Ultimately, Longoria and Argüello weren't as ready for love with each other as they thought they were; the couple split after just four months of dating.

During an April 2023 appearance on SiriusXM's "Jeff Lewis Live," Teddi Mellencamp's "Two Ts in a Pod" co-host, Tamra Judge, recalled how Teddi name-dropped her famous one-night stand on their podcast once. Teddi later regretted sharing that juicy info, however, and asked producers to edit out his name. "So now, I tell people, 'If you guys wanna know, just DM me,'" Judge said. According to Teddi, Judge wasn't joking. "I'm like, 'Stop telling people.' I did not want to out this guy."

But "The Real Housewives of Beverly Hills" alum was willing to drop one big hint about the actor's identity on Lewis' show. "He has a very famous best friend as well," she said. Judge then jumped in to add that his initials are M.D., prompting a producer to guess that the mystery guy is Ben Affleck's bestie, Matt Damon. However, Teddi pointed out that other actors with the same initials include Matt Dillon. "You f***ed him, too?" one of the producers quipped. Teddi also mentioned Michael Douglas, but by then, she had ruled out Damon's "Behind the Candelabra" co-star by revealing that the A-lister in question was around 10 years older than her. She also said that the purported hookup happened when she was 20 and had used a fake I.D. to sneak into a club. 

Fun fact: Teddi's dad, John Mellencamp, once dated Meg Ryan, who starred alongside Damon in the 1996 film "Courage Under Fire."

Sarah Hyland and Wells Adams are rare examples of an actor and a reality star who made it all the way to the altar. While Adams failed to sweep JoJo Fletcher off her feet during Season 12 of "The Bachelorette" in 2016, he had Hyland swooning. The "Modern Family" star tweeted that she was impressed by her fellow ABC family member making a reference to the book "Lord of the Flies," but some of her followers had to reread her #menwhoreadarehot hashtag. When Adams popped up on "Bachelor in Paradise" as the bartender the following year, Hyland celebrated — and Adams noticed. "Taking applications for #BIP5 bar backs now. Please send references. Preferably from Phil Dunphy. I'm kidding the job is yours @Sarah_Hyland," he tweeted.

On "Jimmy Kimmel Live," Hyland revealed that Adams eventually slid into her DMs, and she shared the assertive pickup line that worked on her: "Next time I'm in L.A., I'm taking you out for drinks and tacos." 

The dynamic duo's Twitter flirting and taco date were the first building blocks of a solid relationship. In July 2019, Hyland shared an Instagram photo of Adams proposing to her on the beach. When the couple got hitched in August 2022, Hyland's "Modern Family" co-star Jesse Tyler Ferguson revealed that he officiated their vineyard wedding. That same year, Hyland became a reality star like her hubby. But as the host of "Love Island USA," she aimed to help others find love.