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Want To Freak? Here Are 15 Housewives And The Famous People They Dated

It's always juicy to hear about salacious celebrity hookups, but finding out your favorite reality stars have a history of shacking up with some of Hollywood's most elite is almost too good to be true. When it comes to scoring dates with prominent figures in the entertainment industry, the women of The Real Housewives have ample experience and have earned some well-deserved bragging rights if you ask us. In some cases these ladies were staples on the social circuit long before they signed on to become part of the most popular reality TV franchise around. From award winning actors to business moguls and everything in between, these Real Housewives have bountiful dating lives that would leave any of us green with envy. We're not entirely sure how they accomplished such a spectacular track record for dating celebs, but we're dying to know all of their best kept secrets. Want to freak? Here are 15 Housewives and the famous people they dated.

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15 A Presidential Pairing: Kim Richards & Donald Trump

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Sure, the ladies of the Real Housewives franchise collectively carry an impressive roster of famous former flames. There have been singers, actors, professional athletes, and billionaire businessmen, but how many of these women are able to say they dated the future President of The United States? According to Kim Richards from the Real Housewives of Beverly Hills, she was once romanced by none other than Donald Trump. During a reunion special filmed following the show’s seventh season, host Andy Cohen questioned Richards regarding her rumored rendezvous with the most talked about man in all of America. While Kim didn’t hesitate to confirm that she did have romantic ties to Trump, she didn’t want to go into much detail, stating, “Yes, let’s not get into it. I had dinner with him.” While Kim’s big reveal was slightly gratifying, some of her co-stars were desperate for Kim to spill more tea about her fully-loaded love life. Not missing a beat, Lisa Vanderpump interjected to ask Richards the more probing questions including, “did you see him naked?” The reality star let everyone’s imagination run wild by coyly saying, “Let's just leave it at this! I don't want to talk about the President!” Although their relationship clearly didn’t go the distance, just take a moment to consider how great it would have been to see Kim Richards as the First Lady.

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14 An A-List Affair: Sonja Morgan & Jack Nicholson

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Let’s face it, there are women who would kill for a copy of Sonja Morgan’s little black book full of Hollywood’s most elite and eligible bachelors, but possibly the most famous notch on her bedpost is none other Jack Nicholson. The affluent actor is one of the many men to have shacked up with Sonja, but no one knew of their steamy past until only recently. During a game of “Would Sonja Date Him” on an episode of Watch What Happens Live, Morgan was shown a picture of a celebrity and she was instructed to answer whether or not she would ever date him. When Nicholson’s image popped up on the screen, Morgan suggested that she had already dated the star by responding “Have I? He’s so much fun!” When pressed further about the specifics of their relationship Sonja confirmed that they once dated many years ago, adding, “Who hasn't? Don't forget how old I am and don't forget those days before cell phones—those old answering machines." When Andy asked if her tryst with Nicholson was more than a one-time deal, Sonja responded, “Nobody nails down Nicholson!" before adding that their love affair was "one big sloppy mess" that took place “whenever we could”. We’re sure Jack just loved having his past come back to haunt him live in front of millions of viewers.

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13 When Author Meets Actor: Carole Radziwill & George Clooney

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While Sonja Morgan may take the cake when it comes to having the highest number of celebrity flings, her Real Housewives of New York City co-star Carole Radziwill gets the gold medal for having the most desirable star-studded hookup of all time. Radziwill lived out every woman’s fantasy when she famously dated George Clooney in the late 90’s. The reality star’s revelation came to light in 2012 during an episode of the series when Sonja let it slip that Clooney had shacked up with the journalist and published author for the better half of a year. The subject of George and Carole was brought up once again this past season during the women’s trip to Vermont when they played a colorful game of “Truth or Dare.” Bethenny Frankel challenged her friend to rate her romps with Clooney on a scale of one to ten, and Radziwill didn’t hesitate to say, “He’s definitely a nine.” Of course, no one would expect anything less than a perfect scorecard for the guy who’s commonly referred to as the “Sexiest Man Alive”. It’s safe to say Carole scored big with this one.

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12 Bedding The Butler: Brandi Glanville & Gerard Butler

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Brandi Glanville is certainly no slouch when it comes to getting close and personal with hunky men with famous reputations. While ex-husband, Eddie Cibrian, was an attractive actor with dimples for days, she certainly upgraded when she admitted to having a moment of passion with Gerard Butler. The reality star aired all of her dirty laundry on an episode of Watch What Happens Live in 2012 when she nonchalantly boasted about bedding Butler after meeting at a party one night. Brandi’s admission sent shockwaves through the entertainment world but when TMZ caught up with Gerard to ask him about their alleged hookup his first instinct was to say “Who’s Brandi Glanville?” Not surprisingly, Brandi didn’t take Gerard’s cold shoulder lightly and she adamantly stood by her statement that she once romanced the famed actor. A few months later during an appearance on Howard Stern’s radio show, Butler cleared the air about his rendezvous with the Beverly Hills housewife, telling Stern, “We crossed paths at a beach party and had a little bit of fun.” Gerard went on to explain his reasoning behind his initial denial of their spur-of-the-moment escapade, telling the radio host, “You know what I said - "Who's Brandi Glanville?" - because I didn't know her last name, didn't know she was a celebrity, didn't know she was going to run out and f***ing tell everyone about it!” All in all, Brandi must have felt vindicated after Butler fessed up to getting frisky with her, and she ranks high on the list of Real Housewives to have scored big with a major celeb.

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11 A Cougar’s Popstar Prey: Eden Sassoon & Jesse McCartney

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Bravo audiences were introduced to Eden Sassoon during the most recent instalment of The Real Housewives of Beverly Hills and within moments of her speaking it was pretty easy to see that she was riding a fine line between somewhat entertaining and downright crazy. With those two stand-out qualities, it’s no surprise that she had all the makings of a true reality housewife, but Eden’s wild love life is enough to make anyone want to know more about her. During her stint on the show, Sassoon talked about her love affair with a man she had yet to meet in person who she connected with online, but her daring dating doesn’t stop there. Prior to her days as a Real Housewife, Eden was married and then got divorced by 2008. Eden then surprisingly dated pop star Jesse McCartney for a brief period in 2012. Although Eden was thirty-nine at the time and Jesse was only twenty-five, their considerable age difference didn’t stop the cougar from reeling in the much younger man. Needless to say, the heir to the Vidal Sassoon throne looked more like McCartney’s mother than his love interest, but that’s what happens when you go from divorcee to living on ‘Dreamstreet’ in only a couple of short years.

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10 When Friends Become Lovers: Bethenny Frankel & Eric Stonestreet

Bravo

Although Eric Stonestreet flawlessly plays the part of a flamboyantly gay man on the set of Modern Family, the actor is actually very straight in real life. He bonded with Bethenny Frankel at a Hollywood party a few years back and they exchanged numbers but neither initially knew much about the other's star-status at the time. After talking again, Stonestreet realized that Frankel was the creator of the popular ‘Skinny Girl’ brand while Bethenny was shocked to find out that Eric was a far cry from his television persona. They forged ahead with a friendship but at some point they decided to give dating a shot. After careful consideration the duo decided that their friendship would likely fare better than a full-fledged romance and they decided to go back to being platonic. During a recent episode of Watch What Happens Live, Bethenny and Eric finally addressed rumors of their purported relationship. The Emmy Award winner took the reins when it came to defining their love one-time connection, saying, "We met and I think we both decided that we make much better friends" before adding "But she’s a wonderful kisser!" Maybe it's a good thing Frankel and Stonestreet didn't work out romantically after all...they would have been one seriously strange couple.

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9 A Model & A Mogul: Cynthia Bailey & Russell Simmons

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Cynthia Bailey has been a hot commodity in the entertainment world long before her start as a Real Housewife. The reality star began her career as a successful model and that’s how she linked up with an array of famous faces, including hip-hop mogul Russell Simmons. Cynthia spoke publicly about their past relationship in 2011, telling the press, “I think more than anything he was just persistent, like, borderline stalking at that point because he would just not take no for an answer. He wasn’t my type, you know. He was still wearing the paisley wool shirts and the jeans and he was sending flowers and every second was like, 'Please, please, please, please.” While the star sure didn’t make their connection sound like it was love at first sight, Bailey eventually gave in and agreed to go on a date with the entrepreneur. Apparently all of Russell’s persistence paid off, because he and Cynthia ended up dating for seven months before eventually calling it quits. During that time period Simmons even got down on one knee and proposed to Cynthia…but she turned down the offer. According to the reality star, she ended things with Russell after having suspicions that he was cheating. Turns out, he was – with future wife (and then ex-wife) Kimora Lee Simmons.

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8 Not Quite ‘Newylweds’: Lizzie Rovsek & Nick Lachey

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It seems like most of the Real Housewives have a knack for nabbing famous men and Lizzie Rovsek is certainly no exception. The former Real Housewives of Orange County star used to date boyband member Nick Lachey way back before either of them were married. Of course, Lachey went on to famously tie the knot with Jessica Simpson and starred in a reality show of their very own based around their life as newlyweds, while Lizzie got married to hubby Christian Rovsek in 2009. It was actually Andy Cohen who spilled the beans on Lizzie and Nick’s past relationship after he revealed that when Lachey was a guest on his show he took Cohen aside and said, "Oh my god. This woman that I used to date is about to be an Orange County Housewife.” When Lizzie made her own appearance on Watch What Happens Live in 2014, the host quizzed her about her ongoing fling with the singer, asking, "You dated him both pre and post Jessica [Simpson], right?” Rovsek was taken aback by the question but did eventually admit to getting hot and heavy with Nick on a number of occasions. We have to admit, “Lizzie Lachey” would have had a nice ring to it if things had worked out.

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7 A Random Romp: Sonja Morgan & Owen Wilson

People

Lady Morgan may have a couple of star-studded notches on her bedpost, but her hookup with Owen Wilson is about as unexpected as they come. Of course, Morgan has bragged so much about cavorting with so many Hollywood stars that some people have stopped believing her at this point, but she swears that her quality time spent with Wilson was the real deal. Speaking to Entertainment Tonight, Sonja was unapologetic about her romance with the actor, stating, “Tinsley [Mortimer] said her celebrity crush was Owen Wilson, and I thought she said she dated him. I go, ‘Oh! I dated him, too!’ I met him in New York through some art friends, and then I also saw him while I was out here. Long time ago, a while ago.” While the term “dated” is used loosely when it comes to Sonja, we can only imagine what went down between the high-profile star and the woman who always has a full dance card of men lined up to sweep her off her feet. In a different interview, Sonja dished even more about her active love life, saying, "It's crazy. I don't want to really drop names because everyone says I'm a name dropper." Well, it doesn’t look like she’s going to stop dropping names any time soon!

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6 A Divine Duo: Yolanda Hadid and Julio Iglesias

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Let’s just come right out and say it: Yolanda Foster has dated some seriously well-known (and seriously wealthy) men. Between her marriages to billionaire businessman Mohamed Hadid and famed music composer and songwriter David Foster, Yolanda had undoubtedly lived a lavish life surrounded by all the finer things. However, long before Yolanda linked up either one of her high-rolling ex-husbands, she was engulfed in a whirlwind romance with famed Spanish singer Julio Iglesias. During a trip to Amsterdam with her Real Housewives of Beverly Hills co-stars in 2015, Hadid casually mentioned her romance with the international star. She told the women, “I used to date Julio Iglesias, don't know if you guys know him, but when I was dating him thirty years ago, he was the one who brought me here for the first time.” Lisa Rinna in particular seemed to be impressed by Yolanda’s dating repertoire, telling the cameras, “Wow! Yolanda is more fabulous than you realize. She has little fabulous skeletons in her closet that come out and say, ''Hello, I'm Julio Iglesias!”

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5 A Famous Fling: Eileen Davidson and Jon Voight

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When it comes to having notable dating experiences with prominent stars, the women of The Real Housewives of Beverly Hills clearly dominate compared to the other cities in the franchise. While all of these women definitely brought their A-game, Eileen Davidson gets major points for once dating a true A-lister. Of course, Eileen has been a fixture in the soap opera world for decades but her brush with fame came long before her days as a Bravo star. According to reports, Davidson was very heavily involved with Jon Voight in the late 80’s and their romance went on for several years. Although the couple had a noticeable twenty year age gap between them, it was nothing but a number for the Oscar winner and his leading lady. Eileen and Jon were the real deal – she even accompanied him to the People’s Choice Awards in 1989. This pair was so serious that many assumed Eileen could become the future Mrs. Voight…and step-mother to Jon’s famous daughter, Angelina Jolie. Of course, we all know that the relationship between Eileen and Jon didn’t work out and both went on to marry other people, but it must be a pretty amazing story to tell nonetheless!

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4 A Humorous Hookup: Brandi Glanville & Ben Stiller

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If you’ve ever seen an episode of The Real Housewives of Beverly Hills, you already know that no secret is safe with Brandi Glanville. The crass reality star is never one to hold back, especially when it comes to divulging the dirty details of her various bedroom romps to anyone who’s willing to listen. While most celebrities would understandably prefer to keep their hookup habits confidential from the rest of the world, Glanville is more than willing to tell all about her menagerie of close encounters with the rich and famous. Perhaps one of the most unlikely names on her lengthy list of one-time lovers is none other than Ben Stiller. During a rapid-fire round of questioning on an episode of Watch What Happens Live, Andy Cohen grilled the actor about a rumored romance with Glanville. Stiller admitted to having a casual fling with the future housewife way back when both of them were single and ready to mingle. The frazzled comedian went on to explain the situation further, stating, “It was short-lived and it was fun, I wouldn’t characterize it as a relationship.” To make matters more awkward, Stiller elaborated on just how discreet their former fling once was, telling Cohen, “It was a couple of dates and fun. I’m not sure my wife is even aware of that.”

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3 Moore To Love: Phaedra Parks & Shemar Moore

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Phaedra Parks’ love life has always been a hot topic while she was starring on The Real Housewives of Atlanta, but that was largely due to the fact that she was a well-known lawyer who married a convicted felon. Things really went wild in 2014 when Phaedra’s husband Apollo Nida was sentenced to an eight year prison sentence for bank fraud and identity theft, and Parks had found herself newly single and open to exploring her options. During a 2016 taping of Watch What Happens Live, Phaedra found herself sitting in the hot seat next to hunky actor Shemar Moore and the chemistry between them was difficult to deny. At one point during the show the two stars shared a passionate kiss for all to see and Moore was clearly smitten with his Georgia peach. The feelings were mutual, as Parks gushed about her on-air makeout session, saying, “Oh my gosh! I kissed him more than…hmmm. Yeah, it was quite a lot of kissing…. My lips haven’t…. I felt like I had been violated, but I was happy for the violation! Girl, he gave me life… this man kissed me on the lips!” Four months later when Phaedra made another appearance on WWHL Andy Cohen quizzed her about her relationship status with Shemar. When pressed about her love life, Phaedra coyly stated, “Well, you hooked me up with somebody and we chat from now and then" before saying “we’ll see” in response to Andy asking if she saw them becoming something serious.

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2 A Legend’s Legacy: Adrienne Maloof & Sean Stewart

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When Adrienne Maloof was on The Real Housewives of Beverly Hills, she and her husband, revered doctor Paul Nassif, rarely saw eye to eye. It was no surprise when the couple announced their plans to divorce in 2012, and neither of them wasted much time diving head-first back into the dating scene. While Dr. Nassif was bouncing from woman to woman as a middle-aged playboy, Adrienne decided to sink her teeth into the son of a British rock star. Surely she wasn’t going to let her ex-husband be the only one parading around town with a much younger counterpart. Although Adrienne and Sean Stewart were faced with an almost twenty year age gap, Rod Stewart’s offspring was clearly taken by much older main squeeze. Speaking to People magazine about her tryst with a legend’s son, Maloof told reporters, “This started as a business relationship and now we’re casually dating“ before reiterating, “It’s casual, real casual.” The couple didn’t appear to be as low-key as Adrienne insinuated, as they were often spotted arm-in-arm in various hotspots throughout LA and Las Vegas. Although their fling only carried on for two months, Maloof and her celebrity boy-toy have claimed to remain friends following their split.

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1 Falling For Frasier: Camille Donatacci & Kelsey Grammer

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We all became utterly enthralled by Camille Donatacci during the debut season of The Real Housewives of Beverly Hills for many reasons. For starters, she was the perfect mix of stunning and sassy that the franchise needed, and her carefully calculated ways were both endearing and downright villain-esque. Of course, a major part of Camille’s storyline was that at the time she was married to Frasier star Kelsey Grammer, but their fourteen year union crashed and burned while millions of people watched it all unfold and viewers couldn’t help but feel for the crestfallen reality star. As it turned out, Kelsey had been carrying on a long-term affair with another woman while he was all the way across the country on business. Kelsey eventually married and had children with his mistress, but the divorce between he and Camille was a nasty and arduous one. The two went back and forth in the press with very unsavory things to say about each other. In an interview with Piers Morgan in 2011, Kelsey alleged that his reality star ex was hungry for fame and insinuated that she only wed him because of the character he played on television. I think she married me because I was Frasier. Frasier had this great wonderful life ... he was stylish ... and just a little gay ... Kelsey Grammer is a different story. You got home and Kelsey Grammer was somebody different.” Ouch.

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Sources: Eonline.com, HuffingtonPost.com, Pagesix.com. DailyMail.co.uk, UsMagazine.com

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