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.

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.

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 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.

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."

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.

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.

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."