10 Grown-Up Celebs Who Shamelessly Dated Teenagers

Nothing is off limits when it comes to dating and relationships; you cannot knock someone for what they like. However, when it is borderline illegal, you cannot help but question their character. There is a double standard in the dating world and when it comes to mixed aged couples, there is no difference. When older women go after younger men they are embracing their age and are sometimes labeled as cougars; however, when men go after younger women, they are stepping into a whole new territory. They will often be labeled as pedophiles or child abusers. At the end of the day, man or woman, it is all a bit creepy and problematic; one must question where the line is and when it has been crossed. This act is more common in Hollywood than most would notice. There are scandalous incidents like R.Kelly and Aaliyah, cute incidents like Sam and Aaron Taylor-Johnson, creepy incidents like Doug Hutchinson and Courtney Stodden and confusing incidents like Tyga and Kylie Jenner. Some celebs are repeat offenders and even enjoy the bragging side of having a younger partner in their life; Wilmer Valderrama has a reputation for liking younger women and bragging. He has dated a 17 year old Lindsay Lohan, a 17 year old Mandy Moore and a now 21 year old Demi Lovato. He bragged about taking Mandy’s virginity on Howard Stern’s radio show and reportedly made sexual comments about his time with Lindsay as well. One must admit, the most horrifying aspect of the dating age gap is the level of creepiness that it gives off. Whichever way you put it, love in Hollywood knows no boundaries and at the risk of sounding like a cliché, Aaliyah said it best, “age ain’t nothing but a number” (well for a small group of people, at least).


10 Don Johnson

Miami Vice actor Don Johnson first met actress Melanie Griffith through her mom Tippi Hedren, who he was dating at the time. Their relationship blossomed into more than your standard friendship; the only problem was Melanie was reportedly 14. The two repeatedly denied their relationship although Melanie admits to living with Don by age 15, who at the time was 7 years her senior. They married 4 years later when Melanie was legal (19) and divorced soon after; "We thought if we were married and it still didn't work, we'd divorce." Constantly being labeled as a “sex-kitten”, Melanie played the role pretty well.

9 Milo Ventimiglia

Actor Milo Ventimiglia met his then girlfriend, Actress Hayden Panettiere, on the set of their television show Heroes; she was 17 and he was 29. At first they denied their relationship, but unfortunately the camera does not lie and they could not help being lovey dovey with one another at red carpet events and banquets. When asked about his relationship with Hayden, Milo said, "She and I are close friends. It's only natural that people are going to couple us together." When Hayden turned 18 they were seemingly more honest about the relationship, but still tried to keep it out of the public eye.

8 Chad Michael Murray

One Tree Hill actor Chad Michael Murray had a very public break up with co-star and wife, Sophia Bush. Riding high off of that media frenzy, Chad started a new relationship with a high school student; Kenzie Dalton, who was 17 at the time. When Kenzie turned 18 and still a senior in high school, Chad proposed with an oval cut engagement ring while he was still legally married to Sophia Bush. Kenzi and Chad had a very long engagement and eventually broke up, probably because when you grow up you realize how creepy your situation really was.

7 Sam Taylor-Johnson


Sam Taylor-Johnson was a recently divorced mother of 2 kids when she met Aaron Taylor-Johnson, a very young up and coming actor; 19 years old to be exact. Since being a cougar is in, Sam tried her hand at dating this youngster. At 42 Sam started a relationship that would turn into a marriage and two more kids. She admits that the 23 year age gap has been a struggle. Sam insists that you cannot help who you love; she told Red; “If you love someone, you love someone. It doesn't matter; age, color, c’mon!”. In the spirit of supporting taboo relationships, Sam recently directed blockbuster hit 50 Shades of Grey.

6 Jerry Seinfeld

Jerry Seinfeld now refers to her as “the most wonderful girl in the word”, however, funny guy Jerry had a bit of a scandal on his hands when he met 17 year old high school student Shoshanna Lonstein. Initially, Jerry insisted during an interview with Howard Stern that she was not 17. He later decided to tell the truth during another appearance with Howard Stern, he said; “I didn't realize she was so young. This is the only girl I ever went out with who was that young. I wasn't dating her. We just went to a restaurant, and that was it.” Getting caught in a lie, Jerry was seen trolling the campus of George Washington University, arm in arm with a then 18 year old Shoshanna.

5 Joel Madden

Good girl went bad for approximately 3 years; Disney star Hilary Duff was 16 when she hooked up with pop punk bad boy Joel Madden of Good Charlotte; he was 26. The relationship lasted almost 3 years and seemed to be pretty serious, Hilary gushed about her then beau in Teen Magazine saying, “I don't ever think about being apart from Joel”. She also recently hinted at losing her virginity to Joel. This is the only known incident of Joel hooking up with an underage girl, he has since moved on to wedded bliss with socialite and ex-best friend of Paris Hilton, Nicole Richie, he has two kids and even a new look; times have really changed. At 16 dating an older guy may seem cool but as you get older, it kind of leaves a bad taste in your mouth.

4 Tyga

Rapper Tyga has found himself in a predicament. Normally known for his music career, Tyga is now mostly associated with dating/not dating 17 year old Kylie Jenner. Kylie and Tyga's relationship speculation not only sparked a Twitter war with his ex-girlfriend and baby mama Blac Chyna, and her side kick Amber Rose; but they are regularly photographed hanging out and Tweeting “secret” messages to one another. Although they previously denied ever dating, the proof is in the pudding or in this case, the pictures and interviews. Tyga reportedly credits Kylie with being a great mom (creepy) and recently confirmed their relationship on Instagram. Accompanied by a photo of Kylie, Tyga wrote; "Certain things capture your eye, but only few capture the heart." aaawww, no.


3 R. Kelly

At the tender age of 15, singer and actress Aaliyah ran off and got married to R&B bad boy and future sexual offender R. Kelly, who was 28 at the time. This was R. Kelly’s first known offence into his foray of messing with underage girls. It was reported that Aaliyah lied on the marriage certificate, filling out the age of 18 instead of 15. The marriage lasted 7 months and her parents forced her to get an annulment (with good reason). There has been much speculation about the marriage; however, court documents reportedly showed that the marriage involved abuse and victimization. This situation is uncomfortable simply because of what R. Kelly's future turned into.

2 Joaquin Phoenix (39)

Actor Joaquin Pheonix has proved to be a little out of the ordinary, one might even say unique. So when he started dating 16 year old full time high school student and part time DJ Allie Teilz, no one was really surprised. Allie and Joaquin met of course, in a club where she was playing a set, they bonded over music and when Allie turned 19 they started being more public with their relationship. Allie however, does take some of the blame saying “I had a complete double life and lied about my age, obviously, but I was really getting involved in the music world and starting to meet people. It wasn't a good world for me being as young as I was.”

1 Doug Hutchison (51)

Actor Doug Hutchinson was 51 years old when he married his 16 year old girlfriend Courtney Stodden. This was a scandal that came as a shock to everyone because of the severe 35 year age gap. Seeing them together even looks like a criminal offense; take one look at him, then at his bride, then look at them side by side and see how long it takes you to feel uncomfortable. Courtney’s physical look also drew attention to the already questionable pairing. However, when the world experienced her personality and lack of maturity, they were even more concerned that this was a girl who did not know what she had gotten herself into. Courtney eventually left Doug “to find herself” and participate in a few reality TV shows. They are currently back together because Courtney “had her taste of being single”.



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