We know, we know; old guys dating younger women is the oldest and most cliché trick in the book. And while we don’t need to go into all the reasons why men of a certain age feel the need to have a woman young enough to be their daughter (or in some cases, their granddaughter) on their arms, it’s still kind of a mystery as to why so many females take up with old dudes. Which makes us wonder: is it all about the daddy issues?
Cradle robbing is a popular practice for men, and seeking mates with that father-figure quality occurs often in the female of the species. According to Business Insider, evolutionary psychologists say that younger women and older men often get together because, while fertility lasts only from puberty to menopause in women, it starts at puberty and can extend long into midlife for lots of men. That means there’s a strategic advantage for women to snag an older gent, as he’s had more time to accumulate resources and stability than his younger counterparts, which in turn could make him a more viable partner and father.
Of course, in the case of celebrities, there’s the classic tale of unknown younger women chasing after older celebrity types for the money, the fame, and the perks. And, well… men being men, they eat it right up. Show biz by nature lends itself to those free of spirit and of love. So it’s way more common for famous people to couple up with other famous people twice their age, than it is for your average Joe and Karen. Even though we know somewhere in the back of our brains that two people are super far apart in years, it helps to see a picture of them side by side to help you do the math. So here is a list of 15 young celebs that love to date old dudes, to help you out.
15 Crystal Harris
Might as well start the list off with the most famous cradle robber of all times, The Hef. In June 2011, Hugh Hefner's then fiancé Crystal Harris, who by the way is 60 years younger than the old playboy, skipped out on their wedding and said some not-very-nice things about her (apparently) heartbroken old beau. But as they say... love always finds a way, and some might argue that so do gold diggers, because a year later, the two reunited and broke the news that they once again planned to wed. In 2013, the then 86 year-old Hugh married his 26 year-old fiancé at– where else– the Playboy Mansion, in Los Angeles. Hugh's entire romantic life since founding Playboy in 1953 has been nothing but a series of young s*xpots. His girlfriends, Crystal included, are not only young enough to be his daughter, but they'd be on the young side even for a granddaughter. So what's in it for young Crystal? Hmm... we can't imagine...
14 Kylie Jenner
First they were friends, then they were "dating," then they broke up... then she turned 18! Can anyone keep up with the drama? Kylie Jenner and Tyga have been driving fans wild with their on-again off-again relationship ever since they officially got together in 2014. Considering it was technically illegal for there to have even been an “alleged” relationship between the 24 year-old Tyga and the then 16 year-old Kylie, they didn’t officially come out as a couple until her 18th birthday. However, the pair that were first introduced at Kylie’s 14th birthday party weren’t fooling anyone, especially the media. There were engagement and breakup rumors. They appeared on each other's Instagram accounts. They shot down pregnancy rumors, and they took their romance to the next level via Snapchat with a video of Kylie "kissing" Tyga's grill. Despite all the criticism that followed the two up until her 18th birthday, Kylie didn't seem to have a problem with the 7-year age difference, but regardless, their relationship may have finally come to an end recently, as reports state that after dating for nearly three years the now 20 year-old Kylie finally called it quits with her 27 year-old beau. It looks like Tyga had a hard time keeping up with this Kardashian.
13 Mary-Kate Olsen
Age is just a number, or so the famous saying goes. But when it was first revealed that Mary-Kate Olsen was dating Olivier Sarkozy in the spring of 2012, skeptics were quick to point out their 17-year age difference, stating that the generation gap would surely be the couple’s downfall. Man, did they prove everyone wrong, because flash-forward to 2017, and the pair is happily married. The couple began dating in 2012, and sparked engagement rumors when Mary-Kate was photographed wearing a giant ring on her ring finger in early 2014. On November 27th, 2015, Mary-Kate tied the knot with Oliver, a banker and the brother of ex-French President Nicholas Sarkozy, in a private wedding ceremony held in Manhattan. He was 47 and she was 30 at the time of their vows, but despite their obvious age difference, no one seemed to object to the couple’s union. Olivier has two children from his previous marriage, thrusting the young Mary-Kate into the role of step-mom, but this seems to be a good match for the Olsen twin, as Mary-Kate has always been mature for her age. Congrats, MK, we wish you the best with your middle-aged gent.
12 Ashley Olsen
They must have some kind of twin ESP, because this dynamic duo really does do everything together, and that includes dating old men. Designers and style dynamos Mary-Kate and Ashley Olsen have taken the term "twinning" to a whole new level. Recently, the sisters were spotted out on a double date at Madison Square Garden. Mary-Kate with her 47-year-old husband, Olivier Sarkozy, and Ashley with her new beau, the over-50 art collector and financier, Richard Sachs. Sachs isn’t the first middle-aged fish in the art world sea that Ashley has fallen for. This past summer, she briefly dated the 59 year-old painter, George Condo. Ashley really has a thing for artistic silver foxes, and just like her sister, she has a reputation for giving her heart to men nearly two decades her senior. Be it a famed artist, financier, or banker, the Olsens’ men always seem to have one thing in common: they’re all strikingly older than the petite former child stars. One could speculate that the girls have some kind of daddy complex, because these sisters have both certainly made a habit out of dating up (in years, so to speak).
11 Miley Cyrus
Knowing what we know about Miley Cyrus, it's really no surprise that this wild child was involved in a romance with an older guy when she was just 15. Cyrus dated Justin Gaston when he was 20 years-old, and she was under age. The couple supposedly met through Miley's father, Billy Ray Cyrus, who reportedly signed off on the relationship. So that makes the age difference less illegal? The two later called it quits, as relationships that begin when you are a child rarely last, and Miley's love life has been all over the place ever since. But there is one commonality among many of Miley's beaus, and that's the fact that the majority of them are significantly older than she is. Can we say daddy issues? At age 18, the singer was spotted kissing John Mayer, who’s 15 years her senior, backstage at the Grammy awards, and at 22 she was reportedly "hooking up" with the 43 year-old comedian, Dane Cook. What can we say, Miley is a girl who goes for what she wants, and more often than not, what she wants is a much older dude!
10 Hayden Panettiere
Hayden Panettiere first grabbed Tinsel Town’s attention as the Indestructible Cheerleader on the hit show Heroes, and it was on that super human set that this little cheerleader found herself in love with her much older co-star, Milo Ventimiglia. Their relationship sparked quite a bit of controversy in the media because Hayden was just 17 years-old at the time, and Milo was almost 30. When their relationship went sour, as high school flings often do, she quickly found love again with the heavyweight boxer, Wladimir Klitschko. (Who's even older than Ventimiglia by a few years.) The generationally challenged couple split up briefly in 2012, but eventually found their way back together, and in 2014, the young Nashville star gave birth to her first child with her 41 year-old beau. Sometimes age really does make a difference, and in this case, it appears to be in a good way.
"Crazy In Love," indeed. Now here's one hot power couple with an even more powerful age gap between them. Jay-Z acts young for his age, so it’s easy to forget that he’s actually 12 years older than his wife, Beyoncé. Throughout their nearly 15-year relationship, Beyoncé, 35, and Jay-Z, 47, have seen it all. From elevator incidents and infidelity rumors to smash hit collaborations and adventures in parenting, the fiercely private pair continues to claim the throne of music’s First Family. The duo first met back in 2000, when they collaborated in the studio, and soon their working relationship blossomed, eventually evolving into one of the most powerful A-list couples that Hollywood has ever seen. They recently celebrated their 15-year anniversary, which is an absolute eternity in the world of celebrity relationships, and welcomed twins (Sir Carter and Rumi Carter) into their family dynasty earlier this year. Proving once and for all that, despite all of the rumors, this pair is still "Crazy In Love" even after all these years.
8 Catherine Zeta-Jones
When they first got together the world thought: “Is she crazy? He’s so old!” In the beginning this pair seemed like an odd couple, to say the least, but now seeing Catherine Zeta Jones and Michael Douglas together just feels normal. Although he’s 25 years older than her, the two married in a lavish ceremony just weeks after Douglas’s previous divorce was finalized in November of 2000. The couple remained by each other’s sides through his battle with throat cancer, and her struggle with depression and bipolar disorder. In 2013, it was reported that the duo had split up when Zeta-Jones moved out of their marital home, and critics thought that maybe she had finally left him for a younger man. But after a few months of separation, the couple worked through their issues, reconciled, and are now living together again in marital bliss. In the geriatric dating pool of men over 70, it appears as though Catherine Zeta-Jones clearly picked a winner!
7 Megan Fox
Talk about barely legal! Megan Fox has been very open about having a thing for more mature men, as she has been dating a guy 13 years her senior since the age of 18. Fox had millions of teenage boys (and men of all ages) drooling over her after her role in Transformers, but she only had eyes for Brian Austin Green. Green has been with Fox since before she was legally able to drink, and he was in his 30’s. Although they broke up a couple of times over the years, they eventually got it together and tied the knot in June of 2010. The actress has been very vocal about her disinterest in dating men her own age. “Boys in their twenties are a waste of time,” she said. “They have nothing to offer conversationally; they’re immature.” We couldn't agree with you more, Megs! Dating up is definitely the way to go, and it clearly worked for the now sexy young mother of three.
6 Blake Lively
There are millions of women out there that wish they could clone Ryan Reynolds for themselves, and not just for his abs. But Blake Lively went and snatched him off the market before any of us ever had the chance. Ryan is the type of guy who knows what he wants and goes for it, and that's exactly what he did when he met the hot (and 10 years younger) Lively. The couple first met on the set of Green Lantern in 2010, when Ryan was married to Scarlett Johansson and Lively was dating Leonardo DiCaprio. (Who, by the way, is 12-years older than her.) Are we sensing a pattern here? Anyway, fast-forward to a year later when they were both single and on a double date (with other people) and that's when the sparks really began to fly. "She was on a date with another guy, and I was on a date with another girl," Ryan told People magazine, "That was the most awkward date [from their perspective] probably because we were just like fireworks coming across." And the rest, according to the much older Reynolds, is history!
5 Amber Heard
Right at the top of the list of mis-matched couples that you didn't think would make it to 2017 are Johnny Depp and Amber Heard. Not that the warring actors were in any danger of getting back together after Heard filed for divorce several months ago, claiming that Depp was abusive. As ugly as their divorce proceedings were right out of the gate, the couple did seem to get a bit sentimental as the process went on. "Our relationship was intensely passionate and at times volatile, but always bound by love," the exes said in a joint statement after reaching an out-of-court settlement and confirming the news that their divorce was finally finalized on August 16th of this year. It's hard to tell what was the final straw that caused this 8-year relationship to come to an end, because so many allegations were made by both parties, but we can't help but wonder if their 22-year age difference might have been to blame?
4 Jennifer Lawrence
Nobody can accuse famous young stars, like Jennifer Lawrence, of only being in it for the money, because she is extremely rich and successful all on her own. So why is the 27 year-old actress dating a much much older man, when she can have any young hot guy that she wants? Well, apparently Lawrence and the 48-year-old director, Darren Aronofsky, hit it off on the set of their movie Mother! and are now taking their relationship to the next level. Darren and Lawrence have been dating for almost a year now, but you'd never know it due to their admirable efforts to avoid being photographed next to each other at all times. The two are well into promotions for the provocative thriller, and have so far hilariously and strategically dodged every opportunity to be photographed side by side. This is largely thanks to costar Michelle Pfeiffer, who they have clearly commandeered as a buffer in pictures. Why is this new couple so camera shy? Could it be that they're afraid the media will comment on the fact that he is old enough to be her father?
3 Rosie Huntington-Whiteley
With his gravelly South London tones and her cut-glass vowels, movie action hero Jason Statham and super model turned actress Rosie Huntington-Whiteley are the epitome of a couple that's too hot to handle. The former Victoria's Secret Angel, who is 30, and the Expendables actor, who is 49, started dating after they met on the set of Transformers: Dark Side of the Moon in 2010. They got engaged over the holidays in 2015, but haven't tied the knot just yet. Rosie and Statham recently became first time parents in June, meaning that this model just made a life-long commitment to her much older man. “I have an amazing relationship with my partner,” the former Victoria's Secret Angel tells Harper's Bazaar. “He's by far the greatest influence in my life.” Their relationship is proof that even when you are staring down the barrel of 50, a guy’s still got a shot at landing a super hot model. You just gotta get ‘em while they're young.
2 Melania Trump
Regardless of what you think of them as leaders, you have to admit that the new First Lady, Melania Trump, married one old dude! Now there is a ton of speculation about this couple and why Melania actually married Trump. Dare we say it might have something to do with his loads of cash? So I'm just going to give you just a short, simple, and neutral rundown of the facts of their relationship. Donald Trump proposed to Melania in 2004, when he was 58 years-old and she was 34. The couple married on January 22, 2005. This is Melania's first and only marriage, while President Trump has been married twice before (to younger women), making Melania his third wife. Regardless of what you think of their marriage or political views, it's pretty safe to say that Melania rode her old man gravy train straight to the White House.
1 Sarah Paulson (And An Older Woman, This Time)
Dating older is not just for straight couples, that's for sure. Reports that 41 year-old Sarah Paulson was dating 73 year-old Holland Taylor began to surface after Taylor admitted that she was in a relationship with a woman, and that it was the "most wonderful and extraordinary thing" that has happened in her life. The two actresses met at a dinner party about 10 years ago, but Paulson was dating actress Cherry Jones (who is 18 years older than her) at the time. People began to notice Taylor and Paulson's witty Twitter banter, but nothing was officially confirmed about their relationship until recently. "If my life choices had to be predicated based on what was expected of me from a community on either side, that's going to make me feel really straitjacketed, and I don't want to feel that," Paulson told ABC News. "What I can say absolutely is that I am in love, and that person happens to be Holland Taylor." Good for you, girls! Don't let society or your 32-year age gap stop you!
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