Celebrities have no shortage of rich, beautiful, age-appropriate partners to woo, yet some
of them still get entangled with crushes they can't legally take to a bar.
While the circumstances surrounding these relationships are varied, from Taylor Swift
to Jerry Seinfeld, these grown-up stars all dated teens.
Before The Fast and the Furious franchise star's untimely death in 2013, Paul Walker
reportedly had an often-overlooked pattern of dating teenage girls — some of whom were
close in age to his own daughter, Meadow.
Critics reportedly slammed the I Am Paul Walker documentary that was released after his death
because, according to Jalopnik,
"[…] It seeks to immortalize the actor's life and his accomplishments […] but also
curiously ignores the major controversy surrounding his relationships with underage girls."
According to the Daily Mail, Walker's girlfriend at the time of his fatal car crash was Jasmine
Pilchard-Gosnell, who had
"been dating Walker since 2006 when she was just 16 and he was 33."
Then-25-year-old Chad Michael Murray began dating then-17-year-old One Tree Hill extra
Kenzie Dalton before his annulment to One Tree Hill co-star Sophia Bush was finalized.
Dalton, who played a cheerleader on the CW staple, got engaged to Murray when she was
an 18-year-old high school senior, according to the Daily Mail.
Murray told Us Weekly in 2012,
"She is a little stunner.
She is a sweetheart.
She is my best friend and we have been together a long time."
“OK, um, well, it's over, so…”
The two split in 2013, after a seven-year engagement.
Eventually, Murray married actress Sarah Roemer in 2015, when they were both in their thirties.
"See?
You coulda been a douche too.”
“Well, how do you know I'm not?”
“I can tell."
Milo Ventimiglia dated Heroes co-star Hayden Panettiere when he was 31 and she was 19,
according to the Daily Mail.
And the pair reportedly split in 2009, due in part to the age difference.
A source dished to Us Weekly,
"It was a lifestyle conflict.
They were in very different places.
[Hayden] is young.
She likes to go out in the Hollywood scene and that's not his style."
"You saved my life.”
“Guess we're even now.”
Ventimiglia talked candidly about dating his much younger co-star, telling Mr. Porter,
"Never do it again.
There are things that happen to you in your life that shape who you are.
[…] You learn from it.
You learn a better way of doing things.
[…] Relationships wear on you."
Before Fergie and Justin Timberlake collaborated on "Where is the Love," they were an item
— and depending on what state they were in at the time, Timberlake may not have been
legal.
Fergie told Cosmo,
"One my good friends was dating JC Chasez, and so we'd all hang out with N'SYNC.
Justin and I would go out together and have fun and make out.
We went to Hawaii together, but we were never serious."
Fergie, who sang in the girl group Wild Orchid at the time, later told the Courier Mail that
those smooch sessions went down when JT was 16 to her 23.
When the topic came up on Watch What Happens Live in 2017, Fergie told Andy Cohen,
"It wasn't all that serious.”
“It wasn’t?”
“Can I like pass on this?
Pass.
Plead the fifth."
When Aerosmith frontman Steven Tyler allegedly began hooking up with Julia Holcomb in 1973,
she was 16 to his 25.
"When we met it was just like electricity.”
In an essay for the Life Site, she said her mother even relinquished guardianship to the
rock star, writing,
"A sense of vulnerability came over me, knowing that I was his ward, but we were not married.
[…] He wanted guardianship papers so I could travel across state lines when he was on tour."
"Don't get me wrong, every one of those girls I loved them dearly.
When we made love, we cried.”
Holcomb alleges that Tyler told her mom he needed the papers so he could enroll her in
school.
She also claims Tyler pressured her into having an operation when she was five months pregnant
with his son — a decision both Holcomb and Tyler reportedly regretted.
"Steven and I, our relationship was never the same.
I don't think that I could ever look at him again without thinking about abortion and
my baby.”
According to the book Walk this Way, Tyler said witnessing the procedure "devastated"
him, adding,
"In my mind, I'm going, Jesus, what have I done?"
Brandy was 16 when she reportedly started dating 21-year-old Boyz II Men crooner Wanya
Morris.
They kept their relationship quiet due to the age difference and to protect her clean
image.
She said on VH1's Behind the Music,
"Immediately everything was about my career.
What are you teaching young girls?
Do they fall in love at a young age?
Is that wrong?
Is that a sin?
It just made me feel like I was all by myself and that whatever I'm feeling personally is
going to have to be put to the side."
Morris reportedly left Brandy for another girl — one he wouldn't have to keep secret.
Brandy remembered,
"It felt like somebody had just completely taken my heart out of my body and just crushed
it."
When Seinfeld was still on the air in 1993, a 38-year-old Jerry Seinfeld met 17-year-old
high school student Shoshanna Lonstein in Central Park, according to People.
Lonstein turned 18 shortly after they met, but even shock jock Howard Stern called Seinfeld
out on it, to which the comedian replied,
"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."
Seinfeld talked about the relationship, telling People in 1994,
"I am not an idiot.
Shoshanna is a person, not an age.
She is extremely bright.
She's funny, sharp, very alert.
We just get along.
[…] My interest in her is very proper."
"This woman is different, she's incredible, she's just like me!”
"Now I know what I've been looking for all these years.
Myself!”
According to the New York Post, they dated for five years and split in '98, when she
was 21 to his 42.
Acclaimed moviemaker Woody Allen dated actress Mia Farrow from 1980 to 1992.
But they split after Farrow found photos of her adopted daughter, Soon-Yi Previn, in Allen's
possession.
Allen excused his behavior, telling Time,
"The only thing unusual is that she's Mia's daughter.
But she's an adopted daughter and a grown woman.
I could have met her at a party or something."
"I have an adult relationship with Soon-Yi."
"Whatever they wanna think, I'll take that heat."
Previn's age when she and Woody first got involved is unclear, with Vanity Fair estimating
she was between 19 and 21 — about 35 years his junior.
The couple went on to marry in 1997.
Some guys have a "type."
Actor Wilmer Valderrama's type is apparently… young.
Actress Mandy Moore told People that she and Valderrama reportedly met on a photo shoot
in 2000, when she was 15.
Wilmer being about 4 years older, she said they started dating when she was 16 or 17.
The actor even boasted to Howard Stern about taking Moore's innocence — which Moore denied.
Then, in 2004, a 24-year-old Valderrama reportedly went public with an 18-year-old Lindsay Lohan.
And later, pop star Demi Lovato said she fell head over heels for the actor in 2010, when
she was 17 and he was 29.
"After I turned 18 we began dating.
I think it was love at first sight."
They split in 2016, after nearly six years together, and claim to still be friends.
The Weeknd, who's real name is Abel Tesfaye, and model Bella Hadid reportedly began dating
in 2015, when when she was 18 and he was 25.
The singer told Rolling Stone,
"It just kind of fell into my lap.
If this had happened two years ago — well […] she couldn't."
"What drew you to each other?”
“Um, y'know, I dunno.
I don't really I haven't talked about it.”
Tesfaye revealed that he initially asked Hadid to appear in the artwork for his 2015 album
Beauty Behind the Madness, but she passed.
Their on-again-off-again romance has been making headlines ever since.
In December 2018, Bella told Vogue that he's the "most beautiful person" she knows.
Groupie Lori Mattix alleges that music icon David Bowie took her innocence when she was
about 15, and he was in his mid-twenties on his Spiders From Mars tour.
"I get this phone call that David Bowie wants to take me to dinner."
"I was miss innocence.”
She also described the encounter in some detail, saying,
“He drops the komono off and gets into the bathtub and says, ‘Can you wash my back?’"
Mattix told Thrillist about her alleged first time with Bowie, and also claimed Led Zeppelin
guitarist Jimmy Page — then in his late twenties — was quote, "one of the great
loves of [her] life" when she was a teen.
She said,
"At that point, I was 15 and totally in love with this man […] It became so serious that
Jimmy asked my mom for permission to be with me.
Looking back, he had to be afraid of getting sued for being with such a young girl."
Actor Doug Hutchison married 16-year-old Courtney Stodden in 2011, when he was 51 years old.
The dysfunctional pair became famous as reality stars, appearing on Dr. Drew's Lifechangers,
Celebrity Big Brother, and Couples Therapy.
“What do you have in common?”
“I'm a weirdo, Courtney is...“
“I'm a lover!”
“... a lover, uh.”
In 2018, a 23-year-old Stodden filed for divorce from Hutchison, telling People,
"I feel like I really didn't get a chance to do a lot of things a normal [teenage] girl
goes through and experiences."
"It's been interesting, for sure.”
Stodden's mother, Krista Keller — who had to sign off on the marriage because her daughter
was a minor — eventually came to the same conclusion, telling Radar Online,
"It was very unnatural for her to be with someone that much older and I think the problems
played themselves out."
Tyga and Kylie Jenner didn't go public with their relationship until she was 18, but rumors
circulated that the rapper and the reality star were an item when she was 17 to his 25.
"I'm really young.
I don't wanna look back in 5 years from now and feel like he took something from me when
he's really not that type of person.”
Kanye West, for one, thought the relationship started when Kylie was younger, telling The
Breakfast Club in 2015,
“I think he, I think he got in early.
I think he was smart."
Tyga denied dating Jenner when she was a minor, though he did dish about their romance after
they split in 2017, telling the Breakfast Club,
"You get with with anybody like for the first year, it's magic and then after that you start
realizing a bunch of s---"
Tyga then doubled-down, adding:
"She's younger than me and she's dealing with perception.
I'm older so I can deal with perception."
"Growing up how she grew up, image and perception was everything."
Henry Cavill dated 19-year-old college student Tara King from 2015 to 2016 — when he was
in his thirties.
He told Elle it was natural to question their age difference, but added,
"People say age is just a number.
It's actually real and true sign of someone's maturity.
But in this case, she's fantastic."
The actor noted that he dated a thirty-something when he was 19 too.
When asked what he learned from his own teenage love story, Cavill quipped,
"Things that I can't mention in an article."
Needless to say, King and Cavill's relationship came and went faster than a speeding bullet.
In 2012, 22-year-old Taylor Swift caused a tabloid ruckus when she dated Robert Kennedy
Jr's son, Conor Kennedy.
"There is a lot of talk about you and the Kennedy's these days.”
“…is there?”
“There is.”
“Do tell.”
Right after he celebrated his 18th birthday, the two went public, according to E! News.
Kennedy was still in high school at the time, but Swift described him as a "grown man,"
telling Rolling Stone,
"The way I look at love is you have to follow it, and fall hard.
[…] You have to forget about what everyone else thinks.
It has to be an us-against-the-world mentality."
Swift also caused a stir in the rumor mill when she allegedly bought a house near her
teenage crush.
According to Vanity Fair, the house was reportedly flipped for a profit after the summer fling
sputtered.
According to Us Weekly, in The Carters' song "713," Jay-Z says he first met Beyoncé at
MTV's Spring Break in Cancun in 2000.
That means Beyoncé would have still been a teen while Jay-Z was already in his thirties
at the time.
The Queen also talked about their meet-cute telling Seventeen,
"I was 18 when we first met, 19 when we first started dating.
[…] I really don't believe that you will love the same thing when you're 20 as you
do at 30.
So that was my rule: Before the age of 25, I would never get married."
The pair wed in an intimate super secret ceremony in 2008, when Beyonce was 26.
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