Why do we still have a taboo regarding May-December relationships? In case you didn’t know, May-December relationships feature a large age gap between the two partners. They can be rewarding as well as challenging. The good news is that these issues can be handled just like any other relationship, regardless of age.
As long as men and women have existed, the majority of men have desired much younger women at some point. A lot of biological and societal factors play a role in such relationships, whether it’s the fact that men remain s*xually potent far longer than women closer to their own age or the debatable idea that men become distinguished as the years go by while older women look old. We’re just telling you how it is.
In June of 2011, Hugh Hefner‘s then-fiancée, Crystal Harris, 60 years his junior, bailed out on the wedding and said some unpleasant things about her allegedly heartbroken old beau. A year later, the couple reunited, and on a Saturday, the news broke that they planned to wed again. This time, in a small ceremony at the Playboy Mansion on New Year’s Eve.
Let’s face it. Hugh Hefner is old, but he’s a freak in an enviable way. Since founding Playboy, his entire romantic life has been a series of young, attractive women. These days, his girlfriends, including Crystal, aren’t young enough to be his daughter. They’d be on the young side, even for a granddaughter. We may never see someone quite like Hugh Hefner again, but that doesn’t mean cradle-robbing isn’t a popular practice among men. And women seeking mates with that father figure quality continues to occur today. Here are 15 famous women dating much older guys.
15. Anna Paquin
Anna Paquin and Stephen Moyer fell in love on the set of True Blood, an HBO series in which focuses on dark fantasy horror. The couple grew up in different countries. Paquin is a Canadian-born New Zealand actress who was born in Winnipeg, Manitoba and raised in Wellington, New Zealand, while Moyer is an English actor from Brentwood, Essex, United Kingdom.
13 years seems like a huge age difference, but it’s all a matter of scale. On the show, Moyer plays Bill Compton, a man who robs the cradle when he romances Sookie Stackhouse, a woman played by Paquin, who is roughly 150 years his junior. In real life, Paquin and Moyer have two children together—a set of fraternal twins, a son named Charlie and a daughter named Poppy. In addition, Paquin has a stepson named Billy and a stepdaughter named Lilac from Moyer’s previous marriage. The family of six resides in Venice, Los Angeles, California.
14. Mary-Kate Olsen
Mary-Kate Olsen is the fraternal twin sister of Ashley Olsen. Both girls starred as Michelle Tanner in the ABC sitcom Full House from 1987 to 1995. They went on to establish a company called Dualstar, which produces a wide variety of TV movies and direct-to-video releases featuring the girls. They also embarked on acting and fashion careers, respectively.
While Mary-Kate isn’t very relevant anymore, she seems to be doing much better now than in the past. Back in 2004, she entered a treatment for anorexia nervosa. In 2007, she was hospitalized for a reported kidney infection. She also sent a private security guard to the scene after discovering her close friend, Heath Ledger, unconscious in his bed in 2008.
In 2012, Mary-Kate began a relationship with Olivier Sarkozy, half-brother of former French president Nicolas Sarkozy. In March of 2014, photos surfaced, showing Olsen wearing what appeared to be an engagement ring. The couple got married at a private residence in New York City on November 27, 2015.
13. Paige Butcher
You may have never heard of Paige Butcher, but she is dating Eddie Murphy. She is an Australian model and actress from Perth, Australia. She is known for her sexy and beautiful looks. She has starred in the movies Big Momma’s House 2 and Something’s Gotta Give.
Butcher is known for her privacy, while Murphy, in his later years, is known more for making questionable personal decisions than funny movies. This relationship hasn’t really been in the public eye, so we can’t tell you much. However, the couple has a young daughter named Izzy, who was born on May 3, 2016. Through her relationship with Murphy, Butcher is the stepmother to eight other children from her boyfriend’s previous relationships with Paulette McNeely, Nicole Mitchell, and Melanie Brown. Although Butcher isn’t a household name in the United States, she is smokin’ hot and has an alluring body. She stands at 5-foot-9 and weighs 128 lbs.
12. Sasha Pieterse
Sasha Pieterse is a bit on the young side, as she just turned 21 this February, but she made headlines after going on a photo posting spree with her long-term boyfriend Hudson Sheaffer. The couple reportedly began dating in 2014 when Pieterse was 18 and Sheaffer was 25.
A seven-year age gap isn’t very surprising, though. Pieterse had to grow up fairly quickly. She was born in Johannesburg, South Africa and was raised in Las Vegas before moving to Los Angeles. She became accustomed to a career in showbiz at an early age, as her parents were part of a professional acrobatic dance team who performed internationally. She was homeschooled and graduated at only 14 years old. It was a happy day for Pretty Little Liars fans when Sheaffer proposed to Pieterse on December 22, 2015. We can’t wait to see what their upcoming wedding looks like! Hopefully, it’ll be full of love when it comes to the ceremony and all of its decorations.
11. Coco Austin
Coco Austin and Ice-T had that special something when they got married in January of 2002. The couple renewed their wedding vows for their 10th anniversary at a well-publicized event in Hollywood on June 4, 2011. They announced the birth of their child, Chanel Nicole Marrow, in 2015, without specifying the exact birth date.
When looking at the bigger picture, it doesn’t seem like Ice-T is 59 years old, but he is. His other half is 38 years old, which makes her 21 years his junior. But let’s not forget that rappers are an exciting group of humans who often have the ability to pick up women, regardless of their age. Lucky for us, Austin and Ice-T have been documenting nearly every adorable moment with their daughter. After all, Disneyland is known as the happiest place on earth. More recently, Austin took Chanel to Disneyland for the first time, dressing her 20-month-old daughter in a matching Minnie Mouse t-shirt. Chanel’s first visit to Disneyland was a success.
10. Megan Fox
Megan Fox made headlines when she met actor Brian Austin Green on the set of TV sitcom Hope & Faith in 2004. The couple began dating when she was 18 and he was 30. They became engaged in November of 2006, but it was reported that they ended their engagement in February of 2009. Later that year, Fox was targeted by a group of fashion-motivated criminals known as The Bling Ring, who robbed Green’s home because she was living with him. They were reportedly engaged again on June 1, 2010. However, Fox has stated that she and Green were continuously engaged since 2006.
Fox and Green married on June 24, 2010, in a private ceremony at the Four Seasons Resort on Maui, Hawaii. Fox filed for divorce on August 21, 2015, but by early 2016, the couple reunited and were expecting a third child. Through her marriage with Green, Fox is a stepmother to his son, Kassius, from his past relationship with actress Vanessa Marcil.
9. Beth Ostrosky
Radio personality Howard Stern watched his 20-year marriage blow up in 1999. He met his first wife, Alison Berns, at Boston University through a mutual friend. He used Berns in a self-produced student film about Transcendental Meditation. Stern wrote, “Within a week after our relationship began, I knew I was going to marry her.” The 24-year-olds married at Temple Ohabei Shalom in Brookline, Massachusetts on June 4, 1978. The couple had three daughters—Emily Beth, Debra Jennifer, and Ashley Jade. They decided to separate, and Stern moved from his home in Old Westbury, New York into a 4,000-square-foot apartment in Millennium Tower in the Upper West Side of Manhattan which he bought in 1998 for a reported $4.9 million. The marriage ended in 2001 with an amicable divorce and settlement.
Stern did what any man in his position would do. He immediately found a model who has been on the covers of Maxim and FHM and see if she could hang out with his group of weird friends. Turns out, Ostrosky was able to handle it.
8. Amber Tamblyn
Actress Amber Tamblyn and stand-up comedian David Cross tied the knot on October 6, 2012. If this seems like an odd match to you, try to come up with someone who wouldn’t be an odd match with Cross. Sounds impossible, doesn’t it? Cross isn’t like anybody else in show business, and we love him for it. But he’d be a hard setup.
Despite the objections, the 19-year age difference doesn’t seem to affect Tamblyn and Cross. The couple announced they had a daughter, Marlow Alice Cross, on February 21, 2017. Moreover, Tambyln took to Instagram to joke about her daughter’s name happened to be Dauphinoise Petunia Brittany Scheherazade Von Funkinstein Mustard Witch RBG Cross Tamblyn-Bey Jr. We wouldn’t be surprised if that was the case as she’s the daughter of actor Russ Tamblyn and the goddaughter of Dean Stockwell, Neil Young, and Dennis Hopper. Also, her uncle is Larry Tamblyn, who was the keyboardist in the 1960’s rock band The Standells.
7. Rosie Huntington-Whiteley
This couple won’t let a 20-year age gap stand in the way of their love. The English couple has been together since 2010. Jason Statham is a fan favorite on the Guy Ritchie crime films—Lock, Stock and Two Smoking Barrels, Snatch, and Revolver. Rosie Huntington-Whiteley is a former Victoria’s Secret Angel.
Huntington-Whitely and Statham possess so many qualities of a manly man and a womanly woman that they might’ve been ripped from the pages of a comic book. It goes to show that even in these enlightened times, there’s something to be said for clearly defining who wears the pants and who wears the lace hipster thong panties in a relationship. It was reported that they became engaged in January of 2016. Huntington-Whiteley then announced the birth of their first child, a son named Jack Oscar, on June 24, 2017. Congratulations on the pregnancy! On a side note, we also hope they’ll have a wonderful future together!
6. Catherine Zeta-Jones
This relationship continues to raise questions as Catherine Zeta-Jones is a sweet girl with a sound mind, and Michael Douglas is an old soul with father-like qualities. When we see a guy like this with a girl like that, we can’t help but think of some advice we once received, “Greed is good.”
After being introduced by actor Danny DeVito, Zeta-Jones met Douglas at the Deauville Film Festival in France in August of 1998. The couple became engaged on December 31, 1999 and were married at the Plaza Hotel in New York on November 18, 2000, after Douglas’ divorce was finalized. Their high-profile wedding ceremony cost an estimated £1.5 million and was labeled as the “wedding of the year” by the BBC. They signed a £1 million deal with OK! magazine to release pictures of the ceremony. After that, they had two children—a son named Dylan Michael and a daughter named Carys Zeta—and have reconciled after living separately in 2013.
5. Hayley Williams
Hayley Williams is best known as the frontwoman of Paramore, a rock band from Franklin, Tennessee. The band currently consists of lead vocalist Hayley Williams, guitarist Taylor York and drummer Zac Farro.
Williams is a Christian and regularly discusses her faith in relation to her music. She doesn’t smoke, drink, nor use recreational drugs. She has criticized the judgmental nature of some followers in the Christian community, which disturbed the Farro brothers, whom cited differing attitudes on faith as contributing to their departure from Paramore.
In 2008, Williams began a relationship with New Found Glory’s lead guitarist Chad Gilbert, who is eight years her senior. In 2012, she confirmed her engagement to Gilbert on Christmas Day. They got married on February 20, 2016. The couple reportedly announced that they were separated in July of 2017. What to do in a troubled relationship or marriage? Pray to God and rely on him because he was lovingly placed in your life for a reason.
4. Amal Alamuddin
George Clooney has always been a ladies’ man. Let’s take a look at the women of Clooney over the years! He dated Kelly Preston from 1987 to 1989. He was married to Talia Balsam from 1989 to 1993. He also had relationships with Ginger Lynn Allen, Céline Balitran, Lisa Snowdon, Renée Zellweger, Krista Allen, Sarah Larson, Elisabetta Canalis, and Stacy Keibler.
Clooney generated headlines in the United Kingdom when he popped the question to British-Lebanese human rights lawyer Amal Alamuddin, 17 years his junior, in April of 2014. As a result, he slammed the Daily Mail after they claimed that his fiancée’s mother opposed their marriage on religious grounds. When the tabloid newspaper apologized for its false story, Clooney refused to accept the apology, calling them “the worst kind of tabloid. One that makes up its facts to the detriment of its readers.” In August of 2014, the couple retrieved marriage licenses at the Royal Borough of Kensington and Chelsea of the United Kingdom and were officially married the following month at Ca’ Farsetti by Clooney’s friend, Walter Veltroni, the former mayor of Rome. They adopted a rescue dog, a Bassett hound named Millie, from the San Gabriel Valley Humane Society. They also have a set of twins, a daughter named Ella and a son named Alexander, that were born on June 6, 2017.
For years, many people have argued that men have a natural attraction to younger women because hormones that appear in a female’s body during her menstrual cycle make her look more attractive. Jay-Z has reportedly admitted that he first laid his eyes on Beyoncé when she was only 16.
Today, the arguable king of 21st century hip hop married the queen of 21st century pop. What more do we need to explain? Together, Jay-Z and Beyoncé are the ultimate power couple, having a combined net worth of $1.16 billion. In 2002, they began a relationship after collaborating on the song “’03 Bonnie & Clyde” for Jay-Z’s seventh studio album, Blueprint 2: The Gift & The Curse. They’ve had a fairly private relationship and got married without publicity. Beyoncé suffered a miscarriage, but she got her wish of starting a family, giving birth to a daughter, Blue Ivy Carter, and more recently, a set of twins—a daughter, Rumi, and a son, Sir.
2. Anna Nicole Smith
It’s no secret that 1993 Playmate of the Year Anna Nicole Smith had a very troubled life up until her death in 2007 from an accidental drug overdose. During the final six months of her life, Smith was the focus of renewed press coverage surrounding the death of her son, Daniel, and the paternity and custody battle over her newborn daughter, Dannielynn.
Smith dropped out of high school and worked at Jim’s Krispy Fried Chicken, where she met a cook, Billy Smith, and got married in 1985. While performing at a strip club called Gigi’s, Smith met elderly oil tycoon, J. Howard Marshall, and they began a relationship. He reportedly lavished gifts on her and asked her to marry him several times. As a result, she divorced her first husband. The following year, a 26-year-old Smith and 89-year-old Marshall got married. Smith has claimed that she loved her husband and that age didn’t matter. 13 months after his marriage to Smith, Marshall died in Houston on August 4, 1995, at age 90. Following Marshall’s death, Smith began a legal battle over a share of his estate. Her case, Marshall v. Marshall (now Stern vs. Marshall), reached the U.S. Supreme Court on a question of federal jurisdiction and a question of bankruptcy court authority.
1. Crystal Harris
We’ve already brought up Crystal Harris‘ marriage to Hugh Hefner, but there’s an extremely common pattern among Playboy models who go for older men. Crystal is one of those types of women. Somewhere from above, Anna Nicole Smith is looking down at her with pride and saying, “Damn, this is how I should’ve done it!”
Harris met Hugh Hefner on Halloween of 2008. She appeared as “Co-Ed of the Week” on Playboy.com magazine during the week of October 30, 2008. In 2009, Harris appeared in one season of E!’s The Girls Next Door. In 2010, Hefner signed a recording contract with Organica Music Group. She released her debut single, “Club Queen,” in 2012 and a second single, “True Harmony,” in 2013. She has also co-designed a range of swimwear along with a line of intimates, athleisure, and loungewear.
In January of 2009, Harris started dating Hefner, joining the Shannon Twins after his previous no. 1 girlfriend, Holly Madison, had ended their seven-year relationship. In 2010, she became engaged to Hefner but broke off their engagement in 2011. The couple later reconciled and got married at the Playboy Mansion in a small, private ceremony on December 31, 2012. She was 26, and he was 86.
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