15 Adult Celebs Who Dated Teenagers...And Got Away With It

For most of you, we probably do not need to say this, but let's just get this right out of the way. Adult celebrities should not go out with teenagers. Why? Well for many reasons, but a big one is because they are jailbait.

As anyone could tell you, I am not the most judgmental guy in the world. And when I say that, I am really saying that I pretty much could care less what you do. I am totally a live and let live kind of guy. There is hardly anything that bugs me out. But with all that said, there are a few things that society does not particularly enjoy. You could be a murderer, you could be a terrorist, or you could just be that kind of person that, you know, goes out with people that are underage.

I know this might seem confusing. Say for example you are 33 and go out with a 16 year old and you are not famous. The general consensus is that you should go to jail. But if you are famous? Well it is just party time. Not really. It is still a seriously bad move. Pro tip: If you are over 18, don't date anyone under 18. Not only could get you in a bit of trouble, but let's face it, the whole thing is also pretty nasty.

Here are 15 adult celebrities that dated jailbait.


15 R. Kelly and Aaliyah

Aaliyah was just 15 years old when she started going out with R. Kelly. He was 27 years old and was the producer of her album, which was entitled Age Ain't Nothing But a Number. One honestly can not even make things like this up. The two were secretly married in 1994, but the wedding was annulled because she was not old enough to legally get married. I mean come on, are we talking about high profile musicians, or a family in the Ozarks here? Sadly Aaliyah died in a plane crash, so we will never know how this romance would have turned out. But we do have to say R. Kelly does not have the greatest track record when it comes to relationships, so we imagine there was no future for them anyway.

14 Justin Timberlake and Fergie


These days Justin Timberlake is respected. In fact, he is almost a bit of an elder statesman in the pop music scene, and everyone has to respect his choice of the woman that he hangs out with, Jessica Biel has it going on in pretty much anyone's books. People forget about what he was like when he was in the band N'Sync, and what I mean by that is he dated some pretty young chicks.  He not only dated Britney Spears, but he dated Fergie, who was in a band called Wild Orchid. Nothing wrong with that right? I mean Fergie seems pretty cool, and she is kind of hot too. Well, there is that whole age difference thing though. Timberlake was 23 while Fergie was just 16 years old. That kind of thing does not fly in the real world.

13 Joel Madden and Hilary Duff

Next on the list of kind of creepy famous guys, and their super young girlfriends are Joel Madden and Hilary Duff. The two started going out way back in 2004, although they said they were just friends until she turned 18. When they first started going out, she was 16 and he was 26. When you really think of it, what is creepier, going out with a 16-year-old when you are 26, or hanging out with a 16-year-old girl as friends when you are 26? It is a close call, and both are totally creepy in different ways. She was once asked about losing her virginity and she said "I had a 26-year-old boyfriend. So everyone can make their own assumptions about what I was doing." Okay Hilary, seriously, that is just TMI for all of us.

12 Wilmer Valderrama and Mandy Moore


Man, that Wilmer Valderrama sure is good with the ladies. Actually a lot of the ladies he has gone out with are actually girls, but that does not sound nearly as cool, now does it? One of the so called "Ladies" he went out with is Mandy Moore. Mandy was all of 15 years old when the two first started hanging out, and was 16 when they started going out for real. Wilmer was 20 years old when the two were together, and like the gentleman he is later said that he took her virginity. They broke up after 2 years together. Wilmer has also hung out with a lot of other women when they were under 18. Which is really not a good look for a TV star, and may be part of the reason that he is not a TV star of note any longer.

11 Jerry Seinfeld and Shoshanna Lonstein

We all know a lot about Jerry Seinfeld, he is one of the most famous comedians of all time. He also is totally filthy rich. But how many of us know that he dated a teenager when he was well into his 30s? Well it is true. Seinfeld was 39 and Shoshanna was all of 17 years old when he picked her up when they both were walking through Central Park. Let's face it, she is pretty hot, and she came from a nice family and had some cash herself; it was not like he was picking up some rube. But still, let us repeat this for a moment, he was 39 years old, and she was 17, Totally not cool Jerry, what would you have said if Kramer was dating someone that was still in high school? I bet it would have grossed you out, and we feel the same about you, Seinfeld.

10 Wanya Morris and Brandy


Poor Brandy, Wanya took her for a bit of a ride. She was just a young girl who went on tour with Boyz II Men when she was just 15 years old when she ended up falling for Wanya Morris, who was 21 at the time. Wanya ended up falling for another woman and dumping her, leaving Brandy more than a bit brokenhearted. They did their best not to let the media know about the whole thing, which makes sense because you know, it was kind of nasty. One would think that she would be mostly over it by now, because she is still smoking hot and Wanya is still...well he is still Wanya. Not to say that he is not talented and rich, but he sure does not seem to be up to her level, At least now anyway; it might have been different when she was a kid.

9 Don Johnson and Melanie Griffith

Don Johnson was 22 when he met Melanie Griffith, who was just 14 years old at the time. Johnson was in a movie with Melanie's mother, who was an actress known as Tippi Hedren when he ended up dating Melanie. They moved in together shortly afterwards. They did so with the blessing of Tippi, who needless to say is not going to win an award for mother of the year. As soon as Melanie turned 18, the two got married. They only lasted 6 months or so before they got divorced. Believe it or not, they got married and divorced again later on in life as well. So the question remains, were they just two people that were totally in love and things never worked out? Or are they just both totally insane? You be the judge on that one.


8 Woody Allen and Soon Yi Previn


So in theory, Woody Allen and Soon Yi Previn started going out when she was 19 years old, but they had known each other for a long time before that. Why? Well because she was the adopted daughter of Mia Farrow with whom Woody Allen had been in a long term relationship with. This totally tops the gross out meter. Basically he knew Soon Yi as his daughter, then when she got to be an adult they started going out. I doubt she and Mia exchange Christmas cards, and in fact it is very likely that she wishes she returned Soon Yi to the orphanage where she found her. The one thing that is really odd about this whole thing though is that Allen and Previn are still together after all this time. Who ever would have seen that one coming?

7 Doug Hutchison and Courtney Stodden

These two lovebirds met on line when she was 16 and he was  50 years old. Aww, I mean isn't that like so totally romantic? Courtney initially got in touch with Hutchison because she wanted to take acting lessons, and yes, the two fell in love, got married, and have been a fixture on the reality show circuit ever since. Some people on this list seem a little misguided, some seem a little creepy, but none seem quite as odd as these two do. Let's face it, at this point they both attempt to make a living out of being totally crazy, and hey if they can do it more power to them. Her parents gave her permission to get married, which is also super odd. I mean like, maybe she just could have dated the guy she met online who was 35 years older than her?

6 Miley Cyrus and Justin Gaston


When Miley Cyrus  was just 15 years old, she started going out with Justin Gaston, who was 20 years old at the time. Man, can you imagine if you were her dad? I mean come on, Billy Ray Cyrus must have been so mad about this. I bet he totally went up to Justin and scared him off. Right? Well actually no. Billy Ray was actually the one that set the two of them up in the first place. In fact he called it a "good thing." Creepy much? Once again, how odd is this world that these people live in? If you work at Walmart and set your 15 year old daughter up with someone that is 20 years old you get run out of town on a rail. Well, at least we all know that despite Miley having an odd childhood, she came out completely normal...

5 Elvis Presley and Priscilla Presley

We all know that Elvis Presley was the King. What a lot of us don't know is that he was the king of dating teenagers. Okay, that might sound a little harsh, but Elvis met Priscilla Presley when she was just 14 years old, and he was 25 years old. His parents put a lot of pressure on him to marry her, and they eventually did - when she was 21 years old. They had one daughter together. While their age gap is undeniably super creepy, she claims that they did not sleep together until their wedding night. This barely passes the straight-face test, and even if it is true, doesn't that mean that Elvis was probably playing around elsewhere? Come on, we are talking about Elvis here for crying out loud! The 2 were divorced a few years later.

4 Nick Lachey and Jessica Simpson


Alright, so this one is not that bad.  Jessica was 18 when Nick was 25. In fact that makes her legal even. But what can I say? Jessica is so hot that she needs to be on this list, and not only that but it brings up a bit of an ethical question that needs to be asked. Is there really much of a difference between dating someone that is 17 and someone that is 18? Umm YES!!! When they are 18 the woman is a legal adult. I know it does not matter in one way, but in another way it matters a lot. So guys, I would suggest you steer clear of women under 18 years old. Unless of course you are totally famous, then apparently you can do pretty much anything you want to do in this, or any other area.

3 Tyga and Kylie Jenner

These two lovebirds denied that they were going out for quite a long time, but the fact of the matter is, they were hanging out when Kylie  was just 17 years old and Tyga  was 25. I know, it sounds kind of lame, possibly even sort of illegal, but come on, how could they resist each other? She is related to the Kardashians, and he is a rapper, whose name is pronounced sort of like the word "Tiger" except it is spelled totally differently.  I mean how could they resist each other? They denied the whole thing for quite a long time, at least until Jenner turned 18, then they were all "Yep we are going out." Must be nice to be famous and get away with doing all sorts of dumb and kind of immoral things, or actually maybe it isn't.

2 Kobe Bryant and Vanessa Bryant


Kobe Bryant  and his wife Vanessa have been through a lot together, there is no doubt about that at all. The two met when she was just 17 and he was 21, which on this list almost makes them seem normal. But you know, he was still drinking age when she was in high school, so they qualify. It seemed a few years back when he was accused of sexual assault, and then admitted that he had cheated on her and were heading for splitsville, but that was not the case at all - they made it through that and seem pretty strong relationship-wise.  It just goes to show you, that you can never tell for sure who is going to last and who is not. Sometimes some of these early relationships make it through to the other side, although most of them don't.

1 Paul Walker and Jasmine Pilchard Gosnell

Paul Walker sadly died an untimely death when he was 40 years old; at the time of his death, his girlfriend Jasmine was 23. Now that is a bit of a stretch, but hey, this is Hollywood, and it is not that odd that the star of The Fast and the Furious franchise would have such a young girlfriend. But wait, they had been going out for 7 years at the time, which meant they  started hanging out when he was 33 and she was just 16 years old. That is not only kind of odd, but it is kind of gross. It is one thing to be old enough to be the woman you are dating's father, it is another thing to be old enough to be her father when she is still in high school. Somehow this managed to be kept rather quiet until he passed away, and at that point everyone had bigger things to talk about.

Sources:; Daily Mail; Mirror

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