The long anticipated countdown for reality star Kylie Jenner‘s 18th birthday has finally come and gone, forcing all of us to shut up about the shameful relationship she and Rapper Tyga, have had since she was a 16 year old minor. Recently, Kylie’s 31 year old half sister Khloe Kardashian, addressed her younger sibling’s relationship in an interview with Complex magazine, saying, “I think at 16 I was probably f–king someone that was in their 20s, for sure. I wouldn’t say I was even dating, probably just sleeping with them. But Kylie is not a normal 17-year-old. Kylie is taking business meetings and bought her first house, or she’s going on a private plane with Karl Lagerfeld to take a meeting. That’s not even what people do in their 30s. It’s a rare circumstance, so let’s treat this as a special case.”
So there you have it. According to Khloe’s logic, it’s perfectly fine for an underage teen to sleep with adult men; provided she owns her own home and conducts business meetings on private jets with top of the line fashion designers. It’s hard to say who is more irresponsible in cases like these: the adult who dates the minor, or the guardians of the minor. Even though Kylie Jenner’s minor status has now become history, an 18 year old socialite still really doesn’t have much in common with a 25 year old parent. The new term for the older man that pursues a much younger female is a “Tiger”(the cougar’s counterpart). Go ahead and take a wild guess where that new term came from. Tyga isn’t the first adult male to get away with dating an underage female. Unfortunately, the unlawful theme is quite prevalent throughout show business- still no less creepy.
12. R.Kelly & Aaliyah
Late R&B songstress Aaliyah Haughton, who’s debut album was not so ironically titled, Age Aint Nothin But A Number, married singer R.Kelly when she was just a 15 year old minor and he a 27 year old rising star. Music producer, songwriter and singer himself, R.Kelly wrote much of the adult content on his young wife’s debut album. The couple were married in a secret ceremony in 1994, without the consent of Aaliyah’s parents, who immediately had the marriage annulled as soon as it was brought to their attention the following year. Aaliyah reportedly cut off all ties with Robert Kelly and ceased to have any further contact with him once their brief marriage was annulled, likely enforced by her parents. Shortly after Aaliyah tragically perished in a plane crash at the age of 22 in 2001, R.Kelly ran into legal troubles surrounding a video tape of him having sexual relations with his underage goddaughter. He was eventually acquitted of charges.
11. Courtney Stodden & Doug Hutchinson
One of the creepiest couplings on the list is hands down 51 year old actor Doug Hutchinson, and 16 year old Courtney Stodden, who eloped back in 2011. Though the ceremony took place in Las Vegas, the teen bride did have the consent of her mother, Kristin Stodden, who recently revealed to Radar Online that she now regrets allowing her underage daughter to marry the middle-aged man. Doug told E! in 2011, “We’re aware that our vast age difference is extremely controversial. But we’re very much in love and want to get the message out there that true love can be ageless.” The recent sex tape star, now 20 years old, frequently makes headlines for posting risque photos on her social media accounts. Married now for 4 years, the couple separated briefly back in 2013, but reconciled after appearing together on VH1’s Couples Therapy.
10. Lindsay Lohan & Wilmer Valderamma
Back when Lindsay‘s future looked brighter than it actually turned out to be, the 17 year old Mean Girls star dated Wilmer Valderamma, in 2004. Though the pair were often photographed together, they decided against going public until Lindsay turned 18 that summer. The That 70’s Show star told People Magazine the same year, “We try to keep it more under wraps because it is a lot more meaningful that way. At this point we don’t need all the free press.” By meaningful, we’re sure he meant to say against the law. The pair ended up parting ways just the following year. Undisturbed by the age gap, Dina Lohan would later refer to Wilmer as her daughter’s “first love”. In 2014, Lindsay shared with Ellen Degeneres that the single Over, from her long forgotten debut album Speak, was about her break up with Wilmer.
9. Wilmer Valderamma & Mandy Moore
Now happily coupled up with 23 year old Demi Lovato, who is 12 years his junior, That 70’s Show star Wilmer Valderrama, is known to like ’em rather young. Just before his short and illegal love affair with Lindsay Lohan back in 2004, Wilmer dated 16 year old Mandy Moore, in 2000. The relationship lasted just a brief 2 years, ironically parting ways just as Mandy reached the age of consent. In 2006, the actor bragged about taking Mandy’s virginity on The Howard Stern Show. Mandy would later tell Elle Magazine his words were, “utterly tacky, not even true, and it hurt my feelings because I like him.” Demi Lovato recently admitted to ZM radio she would, “marry Wilmer tomorrow if he were to ever propose.” Wilmer has dated a bevy of young beautiful starlets in the past, including Minka Kelly, Ashlee Simpson, Jennifer Love-Hewitt and Lindsay Lohan.
8. Miley Cyrus & Justin Gaston
Disney alum Miley Cyrus, who recently came out as bisexual after going public with her new relationship with Victoria’s Secret model Stella Maxwell, received a lot of heat back in 2008 when the 15 year old openly dated 20 year old model, Justin Gaston. The illegal relationship took place at the same time that the teenage Miley was best friends with a much older back up dancer, Mandy Jiroux (also 20). The pair were so close they hosted they’re own YouTube channel titled The Miley & Mandy Show. Back in 2008, Miley and Justin met while he was a contestant on the reality TV show Nashville Star, while her father Billy Ray Cyrus hosted. Both Billy Ray and his wife Trisha, were perfectly fine with the age gap between teenage daughter at the time and boyfriend, once referring to the relationship as, “a good thing”. The couple eventually parted ways in 2009.
7. Paul Walker & Jasmine Pilchard-Gosnell
The late Paul Walker tragically lost his life in a car crash in the winter of 2013, leaving behind his 16 year old daughter Willow, and girlfriend of 8 years, Jasmine Pilchard-Gosnell. Many don’t know that Paul and Jasmine met and began their relationship when she was just 16 years old, in 2006. Paul, who had a 17 year age gap with Jasmine, first met her when he was 33. To put it into perspective, Jasmine is just 8 years older than Paul’s only daughter. The deceased actor reportedly had a history of dating teenage girls, according to his ex girlfriend Aubrianna Atwell, who told the Las Vegas Sun that they dated back in 2001 when she was just 16. She said, “I met him at the Hollywood Canteen with a bunch of friends. We just became friends and ended up in a relationship. We have been in each other’s lives ever since.”
6. Jerry Seinfield & Shoshanna Lonstein
Seinfeld star Jerry Seinfeld, reportedly dated a 17 year old high school senior named Shoshanna Lonstein, back in 1993, during the height of the iconic sitcom’s popularity. Jerry (38 at the time of the relationship’s onset) would frequently openly gush that his young love was, “the most wonderful girl in the world” and even addressed their age gap by saying, “Shoshanna is a person, not an age. …We just get along. You can hear the click.” During an interview with Howard Stern in 1993, the sarcastic host even poked fun at the 21 year age gap between he and then girlfriend
5. Hayden Panettiere & Milo Ventimiglia
In 2007, 17 year old Hayden Panettiere developed a close relationship with her 29 year old Heroes co-star Milo Ventimiglia, who awkwardly plays her uncle on the television series. The pair repeatedly denied being involved but were spotted holding hands publicly after her 18th birthday. Milo told Details magazine, “When you’re in the public eye, you try to keep whatever you can private.” The once illegal romance lasted a brief 2 years, ending suddenly in 2009. Hayden has a habit of dating older men. Milo was 12 years her senior, and her current beau, Ukrainian heavyweight boxer Wladimir Klitschko, is 13 years older. The actress has been quoted as saying, “It was never a case of me making a decision, ‘I want to date older men,’ But I am drawn to people who make me up my game, who bring me up to their level. I want to be with somebody who is more worldly than me, somebody who can give me guidance and is completely secure and comfortable with who they are.”
4. Kobe & Vanessa Bryant
In 1999, 21 year old Lakers shooting guard Kobe Bryant, met 17 year old high school senior Vanessa Laine, while she was working as a back up dancer in a music video for Tha Eastsidaz. The two met while Kobe was in a recording studio working on an album that was never released. The 4 year age gap didn’t stop the two from dating right away and getting engaged just 6 months after first meeting. Due to all of the attention she received from her high profile relationship, Vanessa chose not to graduate and instead finished high school through home schooling. When the two finally married in 2001, Kobe’s parents weren’t in attendance due to the fact that they felt the couple was too young for marriage.
3. Chad Michael Murray & Kenzie Dalton
Following a quick marriage to co-star Sophia Bush, and an even quicker divorce after just 5 months, Chad Michael Murray began dating a 17 year old extra named Kenzie Dalton, back in 2006, whom he met on the set of One Tree Hill, while still working alongside ex wife Sophia. The pair wasted no time getting engaged within 2 months of meeting while Kenzie was still a high school senior. Surprisingly the pair far outlasted Chad’s first marriage, carrying on for 7 years before ultimately deciding to split in 2013. Chad was 32 at the time of first meeting Kenzie, and once gushed to Us Weekly, “She is a little stunner. She is a sweetheart. She is my best friend and we have been together a long time.”
2. Kylie Jenner & Tyga
What makes this relationship so disturbing is the fact that Tyga has known Kylie since she was 14 years old. The two first met when the rapper was scheduled to perform at older sister Kendall Jenner’s birthday party in 2010. Many don’t know that the formerly illegal relationship actually began before Tyga’s engagement to ex fiance Blac Chyna, was officially over. In a desperate and futile attempt to revive his flailing rap career, Tyga recently released a music video for his single Stimulated, which features his newly 18 year old girlfriend in intimate scenarios and absolutely cringe-worthy lyrics. The pair were just offered an 8 figure deal by Vivid entertainment to film a sex tape, which we’re surprised to hear Tyga hasn’t rushed to accept, in light of all his reported money troubles.
1. Priscilla & Elvis Presley
While living in Germany for a brief time due to her father’s position in the air force, 14 year old Priscilla Ann Wagner, was spotted by Elvis Presley’s friend and invited to meet the superstar. Upon first meeting Priscilla, a 24 year old Elvis exclaimed, “Oh! A baby! You’re just a kid.” A 9th grader at the time, Priscilla eventually moved in with the King of Rock and Roll at Graceland, while still attending high school. Elvis’ widow claims that in the beginning, it wasn’t the sexual relationship that many naturally assumed it to be, insisting that the era in which they came up, the 1960s, was highly ethical. 7 years after first meeting one another, 21 year old Priscilla married 31 year old Elvis in a Las Vegas Ceremony, and their only daughter, Lisa Marie Presley, was born 9 months later.