8 Celebs Who Have Dated Around The Most (And 7 Who Settled After One Try)

It sometimes seems as if celebrities live in another world entirely, and sometimes, it’s nice for us average people to get an insight into it. And nothing titillates people more than finding out about the dating lives of celebs. It’s juicy gossip that a lot of people just need to know. A lot of celebs do their utmost to keep their private lives private. But in today’s day and age, that’s an impossible task. As soon as high-profile celebs step out – although having said that, even B-list or even D-list celebs go through the same thing – they’re hounded by the media, baying to capture them in an uncompromising position. So, regardless of how hard they may try to keep their relationships under wraps, we’re going to find out who they’re dating. Look through the dating histories of some celebs and, well, let’s just say it makes for some interesting reading. Sure, they have the fame and fortune, live celebrity lifestyles, and seem like attractive propositions, but even so, some of these celebs have dated a hell of a lot of people.

It’s actually quite refreshing to find out about those who haven’t really been in the dating game at all. At the other end of the scale, there are those who met someone and got lucky, and settled with their partner. Among all the scandals and breakups in the celeb world, there are those relationships dotted about that are strong and seemingly unbreakable. These are 8 celebs who are known for their illustrious histories in the dating game and 7 that settled down after one try.


15 Dated Around: Cameron Diaz

via: lifeandstylemag.com

Most people would give their right arm to date Cameron Diaz. No celeb’s gone that far of course, but she has dated a hell of a lot of them. Cameron Diaz is certainly someone you’d call a serial dater. Although now, that should be past tense – she was a serial dater. She has dated Carlos De La Torre, Matt Damon, A-Rod, Justin Timberlake, Paul Sculfor – those are just the ones we know about with certainty. If rumors are to be believed, she’s also dated the likes of Gerard Butler and Bradley Cooper, and plenty of other people during her wild younger days. It’s no surprise that she’s dated so many people. She believed that settling down and getting hitched was a “dying institution” that didn’t suit the modern celebrity world. It’s safe to assume her opinions have changed.

After spending years and years in the dating game, flitting around from one meaningless relationship to the next, Cameron Diaz can thank Nicole Richie for helping her settle down. The two were good friends, and Nicole introduced her to her brother-in-law, musician Benji Madden. After a matter of months, the two got married and have been together ever since.

14 Settled: Courtney Stodden

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Courtney Stodden has been thrust in the celebrity world at a pretty young age. She acquired celebrity status at the tender age of 16, and has since tried her hand at acting, singing, modelling, and she’s got in on the whole reality TV thing, too. Look at Courtney and it’s not surprising she’s gotten so much attention. It’s fair to say that she’s caught the eyes of lots of people, but when she was 16, she caught the eye of one person in particular and ended up marrying him.

She was an aspiring pop singer and wanted to get into the acting profession. She turned up to a workshop, and instantly took the fancy of the teacher, character actor Doug Hutchison. At 16, you’d think that Courtney would want to date, enjoy herself, and not marry the first guy she came across. But that’s exactly what happened. They married, and their relationship received worldwide attention, not because the two of them were megastars or anything, but because of the ginormous age gap; Doug was 51 when they got married! It hasn’t all been plain sailing. Throughout their marriage, there’ve been rumors that they’re divorcing, legally separating, but they are actually settled and are still living together. That’s six years and counting.

13 Dated Around: Pamela Anderson

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Saying that Pamela Anderson is the female Charlie Sheen is a fair to comparison to make, although she may take issue with that. During her younger days – actually, it has been pretty much throughout her time in the limelight, but mainly during her younger days – Pamela was known as the glamorous diva who posed for Playboy and strutted her stuff in front of the cameras for various other lads’ mags and such publications. She was living that lifestyle, was a glamor model, and dated a hell of a lot. She’s been married to Tommy Lee, and they divorced then got back together. She’s also been with Kid Rock. They dated, split up, then got back together and married. Then there’s Rick Salomon to whom she’s been married twice. Swedish model Marcus Schenkenberg was her partner for a bit, then it was Julian Assange. She’s recently been spotted out and about with French soccer star Adil Rami. Those are just the people we know about.

12 Settled: Snoop Dogg

via: nydailynews.com/eonline.com

So-called gangster rappers are perceived to be pretty edgy characters. That normally entails getting up to no good with the opposite s*x: dating lots of women and sleeping around, amongst other things, of course. That’s the generally-perceived stereotype. While it may hold true for some, Snoop Dogg doesn’t fit into that stereotype. No one’s saying that he doesn't have a questionable past. He’d be the first one to admit to that. But when it comes to relationships, there has only been one in his life. Snoop’s been with his high school sweetheart throughout his time in the limelight. They were infatuated with each other in high school, and stayed together, getting married in 1997. Despite a small period of separation, they’ve been rock solid, and are still together and happily married. They’ve had three kids together and are still going strong.

11 Dated Around: Charlie Sheen

via: hollywoodtake.com

It probably won’t come as a surprise to too many of you that the notorious playboy Charlie Sheen is on this list. Remember his character in Two and a Half Men? That was basically a play on his real-life persona. The guy sleeps around, pays for prost*tutes, and embarks on new relationships what seems like every other day. Okay, most of these are purely s*xual relationships – you can’t really say that he’s dated these women. But he has dated a ton of women too. He’s tried to go on the straight and narrow, but dating, and especially marriage, is a no-go area for him – or at least it should be. He dated and had a kid with his high school sweetheart. He was engaged to be married, but shot his fiancé in the arm; yes, you can’t make this kind of stuff up! Unsurprisingly, she broke off the engagement. He then went wild and dated many adult movie stars, including the likes of Ginger Lynn and Heather Hunter. Then there were the three marriages, the two women whom he dated and lived with at the same time, and then a few more adult film stars. I could just go on and on.

10 Settled: LeBron James

via: msdramatv.com/bustle.com

LeBron James is arguably one of the greatest basketball players of all time. He’s been hugely successful, not just on the court, but off it too, where he’s revered and ranked as one of the world’s most popular athletes. Due to the fame and fortune, it could have been easy for LeBron to go off the rails and embark on the type of life that many money-hungry athletes lead. But he’s had a rock by his side to keep him grounded, a strong woman who’s been with him pretty much throughout his entire career. Savannah Brinson was LeBron’s high school sweetheart. They dated for many years before LeBron popped the question and made it official. They married in 2013, and have been happily married, raising their three kids together ever since. Savannah’s been his one and only love, and so for him it was a no-brainer to settle after one try.

9 Dated Around: Taylor Swift

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Stereotypically, it’s men that are often spoken about when it comes to dating the most people. If men date a lot, they’re studs, but if women do so, they’re perceived to be, well, you know the word. Taylor Swift has been called that and a lot worse during her time in the limelight. Haters love to hate, but let’s face it, if Taylor was interested in dating you, you’re hardly going to turn her down, right? There are always rumors about Taylor and who she’s dating, or who she’s having a fling with. But the pop sensation has cast her spell on a number of elite celebs over the years. There’s Calvin Harris, Jake Gyllenhaal and Harry Styles, to name a few. She’s 27, but can already boast a pretty illustrious dating history. Although having said that, she probably wouldn’t want to boast about it. She is probably hoping to find the one and settle, as most people want to.


8 Settled: Kyra Sedgwick

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Kyra Sedgwick makes up one half of what has to be one of the longest marriages in the celeb world. Her and her hubby, Kevin Bacon, have been together for a hell of a long time, since 1988. Their careers have risen together, and today they’re an integral part of the film industry. Both are still going strong too, and are still churning out the movies and TV roles. She met Kevin when she was in her early 20s, and they instantly hit it off, subsequently got hitched, and have been married ever since. I say they met each other in their 20s, and that is when they did first properly meet each other. But they actually met each other many years previously. Kyra, at the young age of 12, had already seen something she liked in Kevin. She was watching one of his plays, and really liked the actor. Her brother told her that if she liked him, she should go and tell him. The young Kyra did just that. Fast forward to 2017 and they’re still together. Marriage really is bliss for these two lovebirds.

7 Dated Around: Kate Hudson

via: usmagazine.com

It might surprise a lot of you that Kate Hudson’s on this list. She generally isn’t perceived to be a serial dater. And for a long period of time, she wasn’t. She was out of the dating game after settling down with Chris Robinson, the frontman for The Black Crowes, in 2000. The two got divorced in 2007, and then it seemed as if Kate was making up for lost time. She missed the dating game and filled her boots. It seemed as if every other week, you’d flick through the pages of a glossy celeb gossip mag, and find that Kate had a new flame. Among those she’s dated since her divorce are Heath Ledger, Lance Armstrong, Owen Wilson, Justin Timberlake, and many many more. She then settled with English musician Matt Bellamy. They were together for four years, had a son together, and were due to marry, but they broke off the engagement. Once again, Kate’s back in the dating game.

6 Settled: Conor McGregor

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Again, most people would perceive MMA and new boxing star Conor McGregor to be a bit of a sleazebag. He may look dapper dressed up in his suit, but don’t let the suit fool you. The guy’s from the street, and is definitely rough around the edges. He grew up with not much to his name, and he grew up fighting for pretty much everything he had. You’d therefore think that Conor’s your typical lad about town – an Irish hoodlum, as certain sections of the media have labelled him. Then there’s his appearance.That scraggly beard, the physique, all those tattoos – just going by looks alone, people would make a snap judgement and would think he’s constantly out on the prowl dating people all the time. But Conor’s actually been with the same woman throughout his time in the limelight. The woman behind Conor’s success is Dee Devlin. They’ve been together since 2008, and she’s been there through all the highs and the lows, since Conor was dreaming of making it big and didn’t have a dime to his name. Now they’re both enjoying the fruits of his labor, are settled, and are enjoying the high life.

5 Dated Around: Sienna Miller

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A lot has been spoken about regarding Sienna Miller and her past relationships. The golden-haired actress has had a ton of high profile romances, and sometimes, they’ve gotten her into plenty of hot water. She’s been accused of being a home-wrecker, having affairs behind people’s backs. It’s rumored she had an affair with Brad Pitt when she was with Tom Sturridge. She’s had an affair with Balthazar Getty while he was still married. Sienna’s admitted to having a relationship with Daniel Craig while she was with Jude Law. You can see where she gets that home-wrecking tag from. Her dating history really does read like the who’s who of Hollywood. It’s no surprise that people find the golden-haired vixen irresistible. Aside from those already mentioned, some of those she’s had real relationships with, are Jamie Dornan, Orlando Bloom, Sean Combs, James Franco, and Hayden Christensen. Sienna is one serious serial dater.

4 Settled: Sharon Osbourne

via: bravotv.com

It’s fair to assume that Sharon Osbourne loves herself a bad boy, and they don’t get much badder than Ozzy Osborne. The guy’s the very definition of rock and roll. He’s lived that lifestyle for pretty much his whole life. There’ve been other metal stars who’ve gotten suckered into that way of life, but none have been more hardcore than Ozzy. By his own admission, due to his crazy antics, he’s lucky to still be here today.

Sharon met her future hubby when she was just a teenager working for her father, who was the manager of his group Black Sabbath. Sharon was 18 at the time. When Ozzy was sacked, she took over management duties, started to date him, and began to manage Ozzy’s solo career. They’ve been married since 1982. It would be a lie to say that it’s all been sunshine and roses. Drugs and alcohol have plagued their relationship. But they’re worked through pretty much everything a couple can work through, and are still together. Sharon settled with Ozzy after one try, and there hasn’t been any other man in her life since.

3 Dated Around: Cara Delevingne

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It might surprise some of you that Cara Delevingne made this list. The superstar fashion model and actress is always in the limelight for something or other. She’s a woman who’s very comfortable in her own skin, says what she wants, and isn’t shy about letting everyone know her business. For a 25-year-old who’s relatively new to the acting profession, Cara hasn’t wasted time going out on plenty of dates. She’s already worked her way through some pretty impressive names, including the likes of Jake Bugg, Gaz Beadle and Jay Electronica. But Cara’s someone who enjoys the best of both genders. She’s bis*xual and has had proper relationships with women too, such as with musician St. Vincent, who she describes as being her first proper love. Her most high-profile relationship has been with big time actress, Michelle Rodriguez. By her own admission she’s had a string of failed relationships, but is still confident in finding the one. We’re keeping our fingers crossed for her.

2 Dated Around: Sean Penn

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Set your eyes on Sean Penn, and you wouldn’t necessarily think that he was a serious lady’s man. But he’s probably got the biggest dating history of most Hollywood stars. Seriously, the number of A-listers he’s dated is just ridiculous, and they haven’t just been flings either, they’ve been serious relationships. Firstly, we’ve got to start with Madonna. They were married for four years in what was a marriage that was marred by violence and other bouts of controversy. Then he got married to Robin Wright, after having a relationship with the singer named Jewel in between. Charlize Theron is another A-list star he’s had the pleasure of dating. They were actually engaged at one point, but Charlize broke things off. He’s currently dating a woman 32 years his junior, Leila George, who’s Vincent D'Onofrio's daughter. Who Sean Penn is dating is always the subject of plenty of media speculation. He hasn’t yet found the one, but at least he keeps celeb gossip-hungry fans entertained.

1 Settled: Heather Morris

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Actress, dancer, singer and model Heather Morris is known for her role in the hit series, Glee. She played the role of Brittany S. Pierce in the Fox musical comedy drama, and became a teen icon. The cast members of that show engaged in quite a few on-set relationships. Some blossomed, but some were just short-term romances. There were always rumors circulating that Heather Morris was dating someone or other from the show. But there’s only been one man in her life. That man is Taylor Hubbell. They first started dating when he was playing college baseball, but they knew each other, and Heather liked him way before he was in college. They went to the same high school, but never hung out. When Heather moved to LA, Taylor hit her up on Myspace, and pretty soon the start of something special had begun. In 2011, Heather was saying she was ready to marry him, have his kids, and give up acting if that’s what it took. Five years later they were married and had added two kids to their family.


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