The most controversial age gaps in Hollywood relationships

·Contributor
·8-min read

Age gap relationships are nothing new; however in 2022, questions are (and should be) raised about the difference if the power dynamics are skewed or if one person in the couple is particularly young.

Singer and songwriter Demi Lovato has released a single this week that takes aim at her ex-boyfriend Wilmer Valderrama who she started dating when she had just turned 17.

In the song, 29, she reflects on the relationship now that she is the same age as Wilmer was when he and her started dating.

Actor Wilmer Valderrama and singer Demi Lovato stand together smiling at an event
Actor Wilmer Valderrama and singer Demi Lovato had an age gap relationship when Wilmer, who was 29 at the time started dating Demi when she was just 17. Photo: Getty Images

The lyrics include: "Petal on the vine / Too young to drink wine / Just five years a bleeder / Student and a teacher / Far from innocent / What the fuck's consent? / Numbers told you not to / But that didn't stop you," suggesting that she does not look back on the relationship positively.

She goes on to comment about his current relationship with fiancée Amanda Pacheco singing: "I see you're quite the collector / Yeah you're twelve years her elder / Maybe now it doesn’t matter / But I know fucking better."

Wilmer also dated Lindsay Lohan when she was 18 and he was 24, and Mandy Moore when she was 16 and he was 20.

But Wilmer isn't the first guy (or gal) in Hollywood to date someone much younger.

Dane Cook and Kelsi Taylor

Comedian Dane Cook, 50, recently got engaged to his much younger girlfriend Kelsi Taylor, 23. The couple had been dating for five years when Dane got down on one knee this month.

Some Twitter users were not impressed with the huge age gap.

"Disgusting tbh. I don't care how 'mature' an 18yo is.

"No reason for a 45yo man to be dating someone with zero life experience," one person wrote on Twitter.

"I will always approve of Dane cook slander… also it's just gross AF why would you want to date someone who is so far removed from your own life experiences," another added.

Someone even commented that Kelsi's mother was only 40!

Comedian Dane Cook and Girlfriend Kelsi Taylor stand smiling together at an industry event
Comedian Dane Cook admits that fiance Kelsi Taylor wasn't even alive for the first 26 years of his life! Photo: Getty Images

Dane isn't interested in what others think about their relationship though.

"Here's the thing: I love her," he told Jimmy Kimmel on Jimmy Kimmel Live!, in 2019.

"She's the kindest, sweetest, just my favourite, my best friend.

"And sometimes I actually find myself saying like, 'Where has she been all my life?'

"And then I realise she wasn't alive for the first 26 years of it," he added.

Leonardo DiCaprio and Camila Morrone

Leonardo may be notoriously private about his personal relationships (he rarely poses on the red carpet with his girlfriends), but that hasn't stopped people from pointing out that he hasn't dated anyone over the age of 25, even as he's aged.

Leo, now 47, not only seems to like dating beautiful women, but they tend to be younger as well.

Leonardo DiCaprio and Bar Refaeli sit together at a Lakers game enjoying some popcorn
Leonardo DiCaprio dated model Bar Refaeli for five years, breaking up when she was 25. Photo: Getty Images

He dated supermodel Gisele Bündchen for five years starting when she was in her late teens.

He then moved on to Israeli model Bar Refaeli, when she was just 20 and 10 years his junior, with the couple eventually splitting up when she was 25.

After that came other young early 20 models including Erin Heatherton, Kelly Rohrbach and Nina Agdal.

Leonardo DiCaprio and Camila Morrone together at 92nd Academy Awards, Camila smiling up at the camera from behind Leo as he greets another guest
Leonardo and model Camila Morrone (directly behind him) have been dating since 2017 despite their 23 year age gap. Photo: REUTERS

He has been dating his current girlfriend, model and actress Camila Morrone, 25, since 2017 so maybe she'll be the one to change him.

Kaia Gerber and Austin Butler

It would seem that the 10-year age gap between actor Austin Butler, who has just turned 31, and model Kaia Gerber, 20 isn't that big a deal.

However a resurfaced picture of Kaia meeting Austin's ex-girlfriend of almost a decade Vanessa Hudgens, has made people re-evaluate Austin and Kaia's relationship.

Austin Butler and Kaia Gerber stand together at the 2022 Met Gala
While private about their relationship, Austin Butler and Kaia Gerber did attend the 2022 Met Gala together in May this year. Photo: Getty Images

The picture recently resurfaced on twitter with the caption: "His ex meeting his new gf," showed Kaia when she was just five-years-old meeting Vanessa at the premiere of High School The Musical 2.

Actress Vanessa Anne Hudgens with actress/model Cindy Crawford and her children and Mini Mouse
Actress Vanessa Hudgens meets model Cindy Crawford and her children Presley and Kaia at Disney's High School Musical 2 world premiere. Photo: Getty Images

Seeing Kaia at such a young age with Vanessa has got the internet riled!

"I’m crying I thought this was a meme but it really is Vanessa Hudgens meeting Kaia Gerber pls Austin Butler is so nasty for this," @agapethamar tweeted.

Whereas others saw it for what it was.

"I have nothing against age gap couples (as long as they are legal) but this picture of Vanessa Hudgens meeting Kaia Gerber is THE FUNNIEST thing I’ve ever seen."

Actress Vanessa Hudgens with model Cindy Crawford and children at a Disney Movie premier, Vanessa and 5yo Kaia shaking hands
Vanessa Hudgens was 20 and Kaia was just five when they met at the Disney movie premiere. Photo: Getty Images
 Actor Austin Butler and actress Vanessa Hudgens stand together smiling at movie premiere
Ex-couple Austin Butler and Vanessa Hudgens arrive at the LA Premiere Journey 2: The Mysterious Island in 2012. Photo: Getty Images

But according to Page Six sources, Kaia is very happy in her blossoming relationship and has the approval of her parents Randy Gerber and Cindy Crawford.

"Kaia thinks Austin is a sweetheart.

"They’re having a lot of fun getting to know each other," the source said adding that Kaia’s famous parents were "supportive of the relationship."

Madonna and Ahlamalik Williams

Madonna's recent ex-boyfriend, Ahlamalik Williams, is not only 35 years her junior but she was also his boss when they met.

The couple, who were together for three years until they broke up in May, originally met when dancer Ahlamalik joined her Rebel Heart 2015 tour when he was just 21.

Ahlamalik Williams and Madonna standing together on the red carpet wearing alternative fashion
Dancer Ahlamalik Williams dated Madonna for three years despite their 35 year age gap. Photo: Getty Images

When they started dating in 2019, Madonna, 63 even had the support of Ahlamalik's parents.

"She told us she is so much in love with him and that we didn’t have anything to worry about as she was going to take care of him," father Drue said at the time.

“We know there’s a huge age gap between the two. Madonna is two years older than me.

“I asked him how he feels about her and he says he has never been happier," he added.

Don Johnson and Melanie Griffith

Don Johnson was 22 when he first met 14-year-old Melanie Griffith on the set of the 1973 film The Harrad Experiment in which Melanie's mother Tippi Hedren was starring.

"She fell almost instantly in love with him.

"It was an adolescent crush," Tippi revealed.

"Here, my daughter was showing signs that I had never seen before in her, with an older man, and there was just sheer panic,” Tippi told The Hollywood Reporter.

"How do you handle that?

"There was a very strong attachment between the two of them," she added.

Actress Melanie Griffith with her boyfriend, actor Don Johnson, and her mother, actress Tippi Hedren laughing and smiling in an old black and white photo
Actress Melanie Griffith with her boyfriend Don Johnson, and her mother, actress Tippi Hedren, in 1973 when they first started dating. Photo: Getty Images

"I was sceptical because of her age," Don said.

"But she was more woman than most of the girls I’d been going out with.”

The two moved in together when Melanie was 15 and got engaged when she was 18.

Their first marriage barely lasted six months before they split.

However, they reunited and remarried 12 years later in 1989 before separating and divorcing again in 1996.

Sylvester Stallone and Jennifer Flavin

Proving that age gap relationships can work if both people are mature and have common interests are Sylvester Stallone and Jennifer Flavin.

Actor Sylvester Stallone and date Jennifer Flavin standing together in the late 80s
Sylvester Stallone and Jennifer Flavin when they started dating in 1988. Photo: Getty Images

Jennifer was 19 and Sly was 42 when the couple first got together in 1988 and despite the on-off nature of their relationship early on, they have now been married for 25 years and have three daughters together.

Sylvester Stallone and Jennifer Flavin Stallone stand together at a function in 2022
Sylvester Stallone and wife Jennifer Flavin Stallone have recently celebrated their 25th wedding anniversary. Photo: Getty Images

"Happy 25th anniversary to my amazing wife," Sylvester wrote on Instagram to celebrate their anniversary in May.

"There is not enough words to describe what this incredibly selfless dedicated, patient, woman has meant to our lives and I only wish they could be another 25!

"Thank you sweetheart!"

"Happy 25th wedding anniversary to us!

"🥰❤️❤️❤️ Thank you for always keeping me laughing, loving and protecting our beautiful family!" Jennifer wrote on her account in reply.

"Our marriage keeps getting better every year!

"I can't wait to spend the rest of our lives together!🥰❤️❤️❤️" she added.

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