Whenever a celebrity’s relationship with a younger partner is questioned, their response always ends up being the same cliché line, “age is just a number.” As if that that gives valid justification to their questionable relationship with someone underage.
In Hollywood, it’s apparently the norm to engage in relationships with severe age gaps, but there is more to it than just being a cougar or a certifiable ladies’ man of all the ages. However, when it comes to these famous men, they shamelessly flaunt their romance with minors. From stolen moments captured by paparazzi or front and center on the red carpet, the duos comprised of different generations put their love affair on full display.
While there have been celebrities who have dated or even married teenaged partners, these fifteen men didn’t wait until things were legal to take their kinship to the next level. Despite the media attention and mostly negative backlash received, these head-turning lovers continued to boastfully parade their connection around as if laws were not being broken.
Whether supporting the underage relationships or not, one thing's for sure, these couples weren’t shy about their former and present rendezvous.
15 Milo Ventimiglia
Just like many relationships in Hollywood, actors Milo Ventimiglia and Hayden Panettiere couldn’t deny their chemistry while on set. The Heroes co-stars began dating when Panettiere was just seventeen years old; she was twelve years his senior. At the start of their relationship they kept their personal involvement hidden from the public, but it didn’t take long for the dots to be connected. From lingering touches on the red carpet, to paparazzi capturing hidden private moments on set, the actors’ romance eventually couldn’t be ignored. While just over a decade separated the duo, they dated for two years before going their separate ways. Since their breakup, Ventimiglia hasn’t been able to settle down with one woman, but found success on the breakout hit NBC family drama, This Is Us, last year. Panettiere went on to add a little lady to her life when she and her fiancé, Wladimir Klischko welcomed a daughter in 2014.
14 Chad Michael Murray
When One Tree Hill star Chad Michael Murray and his beautiful co-star Sophia Bush called their brief marriage quits due to rumored infidelity on his end, the actor was quick to find love again. In the small North Carolina town in which the infamous high school basketball television drama series was filmed, Murray began dating Kenzie Dalton, a local extra on the show. Long before the ink could dry on his divorce papers, the twenty-four-year-old began an affair with the seventeen-year-old former pageant queen. Despite still being a senior in high school, and an already failed marriage, the duo was soon engaged to be married. While Murray praised his teenaged girlfriend during interviews, the couple wasn’t able to survive their seven-year long engagement and finally called it quits in 2013. The former heartthrob has since moved on to another of his co-stars, Sarah Roemer, when the pair married in 2015. The couple recently announced they are expecting a second child early this year.
13 Joaquin Phoenix
Joaquin Phoenix has taken the entertainment business by storm with his impressive resume in both the film and music industries, but his private life proves to be much more questionable. In 2013, the Walk the Line actor made a public debut with his much younger girlfriend, Allie Teilz. Despite two decades separating him and his new love, the thirty-nine-year-old actor shamelessly walked hand-in-hand with his gal as paparazzi snapped picture after picture. While the professional teen DJ was clearly of legal age when the couple was first seen together, rumors swarmed that the pair has been together prior to her entrance into adulthood. Seeing as Phoenix keeps his personal life as secret as possible, it’s unknown the exact moment the couple really began their love affair. The actor and his young partner were together for nearly two years before ending their head-turning relationship.
12 Wanya Morris
Before Wanya Morris was moving around the dance floor of ABC’s hit reality show, Dancing with The Stars, the Blackstreet singer was putting the moves on singer Brandy. Despite having a strict mom as her manager who was trying to protect her image, the sixteen-year-old R&B singer began dating Morris, despite it being highly frowned upon by her management team. Five years older than the young singer, the artistic couple had no choice but to hide their romance from the public eye and shut down any rumors of a relationship. But like most love created in Hollywood, the pressure of time consuming schedules and stresses of their career led to the demise of their relationship. In the case for the former couple, Morris left Brandy for another woman, two years into their courtship. Their duet on Brandy’s single, “Brokenhearted”, never felt more real for the young singer during the end of their love affair.
11 Joel Madden
Hilary Duff is constantly praised for her ability to stay grounded unlike her fellow former Disney Channel stars, cough cough, Miley Cyrus. However, there was a brief moment of hesitation when the actress began a relationship with Joel Madden. At just sixteen years old, the teen idol tried to keep her relationship with the Good Charlotte musician on the down low, for he was nine years older than her. However, like any secret in Hollywood, it eventually surfaced that they were in a relationship. In an interview to Cosmopolitan, Duff didn’t hold back about what she and her former boyfriend were up to during their two-year long relationship, "I had a 26-year-old boyfriend, so everyone can make their own assumptions about what I was doing." Read between the lines if you will. While the actress has been unlucky in love with a divorce to her young son’s father that became official last year, Madden went on to marry television personality Nicole Richie as the couple welcomed two children prior to their nuptials.
10 Justin Gaston
It’s no secret that Billy Ray and Tish Cyrus have supported all of Miley’s questionable stage performances and recent wardrobe in the past few years, but it was when the Cyrus patriarch allowed his daughter to date an older man that people started getting concerned. At just fifteen years old, Miley Cyrus was introduced to a twenty-year-old Justin Gaston by her father. The duo was seen on multiple occasions together, surrounded both by Cyrus’ family and alone. Many questioned the reasoning as to why the entertainer’s father would approve of the relationship especially when the underwear model proved to be much older than the former clean-imaged child star. However, the negative attention died down once the puppy love came to an end. Cyrus then went on to twerk her way through a new appearance and an on again, off again romance with her hunky Australian Last Song co-star Liam Hemsworth, while Gaston and his wife recently welcomed a baby girl last year.
9 Don Johnson
While it’s very common for co-stars of a television series or a motion picture to find love off camera, it’s almost unheard of for family members to find romance with the actor instead. Especially, when it’s a co-star’s daughter. This was the case for Don Johnson when he began dating his The Harrad Experiment co-star’s fourteen-year-old daughter, Melanie Griffith. The following year, the couple began living together and became engaged three years later once the actress became of legal age. Despite being seven years older than the young actress, the two were married for half a year in 1976. However, after both experiencing failed relationships after their divorce, the former husband and wife reunited in 1988 and remarried the following year, the same year that they welcomed their daughter, Fifty Shades of Grey actress, Dakota Johnson. While they gave their love a second shot with marriage, they called it quits once again just six years following their second union.
8 Steven Tyler
Steven Tyler clearly didn’t want to miss a thing when he began dating women of a younger age pool. In 1975, the Aerosmith front man began a cringe-worthy relationship with Julia Holcomb. It was reported that Tyler was handed over guardianship of the fourteen-year-old groupie in order for the pair to be together. For three years, the singer and his young gal partied and lived up the music scene until their final separation. From substance abuse to a demanding concert tour, the former lovers couldn’t withstand the chaos. Prior to their breakup, Holcomb became pregnant with the “Dream On” singer’s child. However, the pregnancy ended the same time of their relationship. While Holcomb disappeared from the public eye following the breakup, she emerged telling her side of the story and voicing her now very public pro-life stance as a Christian motivational speaker.
7 Wilmer Valderrama
The That '70s Show actor, Wilmer Valderrama, found success early on in his career and with the young ladies of Hollywood. He first began dating underage girls when he met teen pop star, Mandy Moore when she was just fifteen years old. Despite the five years separating them, things were hot and heavy with them until they called it quits. From there, Valderrama continued engaging in relationships with young celebrities. Just four years after dating Moore, the actor started dating a seventeen-year-old Lindsay Lohan. Needless to say that relationship was just as successful as Lohan’s first stint in rehab. And to round out the trio of his younger women, Valderrama was twenty-nine years old when he began a love affair with Demi Lovato. Having started dating when she was just seventeen years old, the singer and her older From Dusk Till Dawn beau were together for nearly seven years before calling it officially quits in 2016.
6 Paul Walker
Despite living a very private life away from the spotlight, Paul Walker was a beloved actor who broke many hearts with his tragic death in 2013. With a respectable film resume, the blue-eyed heartthrob was a welcomed addition to any screen. When not filming another addition to the Fast & Furious franchise, the actor was spending time romancing younger ladies. Following his devastating passing, it was revealed that Walker was in a seven-year-long relationship with a twenty-three-year-old, Jasmine Pilchard-Gosnell. Which means that when the pair first started dating she was just sixteen years old; exactly twelve years younger than the Into The Blue actor. Perhaps why the movie star chose to live a quiet life when not on the big screen? Nonetheless, Walker was incredibly down to earth and used his celebrity status as a platform to raise awareness to environmental causes and clearly wasn’t interested in romancing the stereotypical Hollywood woman.
5 Jerry Seinfeld
Funny-man, Jerry Seinfeld, didn’t have many laughing when he began dating a much younger Shoshanna Lonstein in 1993. Following an impromptu meeting in Central Park, the Seinfeld actor and high school senior traded numbers prior to their underage love that quickly blossomed into a mature romance while under much scrutiny from the public eye. The twenty years separating the couple wasn’t well received due to the large age gap and the fact that they began dating before Lonstein could legally vote. While Seinfeld claims his former flame turned eighteen soon after they met, it wasn’t enough to calm the negative feedback. After dating for nearly five years, their once cringe-worthy relationship officially ended. A year later, Seinfeld met is now wife, Jessica Sklar, as Lonstein went on to become an accomplished fashion designer and welcomed three children with her husband before divorcing him last year.
4 Kobe Bryant
Oh love and basketball, isn’t it sweet? Not when one partner of the relationship is a minor. Just at the start to his dominant career with the Los Angeles Lakers, Kobe Bryant met a seventeen-year-old Vanessa. Despite him being four years older, the NBA star couldn’t deny his attraction to the high school senior. Their relationship quickly heated up forcing his now wife to drop out of high school. With the, mostly, negative attention she received from her fellow peers, Vanessa wasn’t able to withstand the spotlight that her relationship attracted. While their relationship hit a few bumps along the way, they have managed to keep their love alive. Today, Mr. and Mrs. Bryant have been married for fifteen years and have three daughters. Their youngest joined their family in 2016 when Vanessa gave birth to Bianka Bell, joining her two older sisters, Natalia Diamante and Gianna Maria-Onore. He shoots, he scores.
3 R. Kelly
The former professional basketball player turned singer-songwriter, R. Kelly, may receive great attention for his music abilities, but nothing can compare to his rap sheet of illegal issues. One of the most prolific stints was his marriage to the young singing protégé Aaliyah when she was just fifteen years old. After meeting three years prior, the teen began working with Kelly on her music career as he produced her first album. On that album, the single entitled “Age Aint’ Nothin But A Number” should have been the first clue that their professional relationship was moving past the point of friendship. Things escalated when the pair married using a false marriage certificate that showed Aaliyah to be of legal age. Quickly following the nuptials, the union was annulled much in part due to Aaliyah’s family, who didn’t give their young daughter permission to marry the older R&B artist. Their marriage was dissolved and the two went about their music careers until Aaliyah’s tragic death in 2001.
The Kardashian/Jenner clan is notorious for making headlines, and not always for positive attention. This time all their money and fame couldn’t overshadow the fact that rapper Tyga, was pursuing a much younger Kylie Jenner. While they didn’t officially go public with their relationship until the lip cosmetic entrepreneur turned eighteen, it was obnoxiously obvious that Jenner and Tyga began their love affair when the television personality was just sixteen years old. From social media posts to public conformation from Jenner’s brother-in-law, Kanye West, it wasn’t hard to ignore that the two were hooking up long before she was able to officially be considered an adult. Now that their romance is legal, the two flaunt their love for all of Instagram to see with borderline inappropriate poses. The couple has even gone so far as getting tattoos to permanently ink their connection to one another. Here’s hoping they won’t be needing to be covered up in a few years.
1 Doug Hutchison
When the fifty-one-year-old actor, Doug Hutchison, announced his engagement in 2011, many were extremely hesitant to offer an order of congratulations for there was just one minor detail; his bride-to-be was a minor. After signing up via the internet to take an acting workshop taught by Hutchison, the sixteen-year-old future Mrs. Hutchison, Courtney Stodden, had to receive permission from her parents to legally wed her older man following their secret courtship. After much controversy in the media, the apparent fame-craving couple officially tied the knot in 2011, despite their significant age gap. Despite being called a “pedophile”, the newlyweds seemed to be proving their haters wrong up until 2013 when they separated. However, their break didn’t last long before they reunited a year later and happily continued their relationship only to break devastating news that Stodden suffered a miscarriage last year.
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