Milo Ventimiglia and Hayden Panettiere
Milo Ventimiglia met Hayden Panettiere on the set of Heroes — where he played Peter Petrelli, and she played Claire Bennet. At the time, Panettiere was 17 years old, and Ventimiglia was 29. Shortly after Panettiere’s 18th birthday, the two announced their romantic relationship.
They broke up after two years. In an interview, Panettiere explained, ”It was never a case of me making a decision, saying, ‘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.”
Johnny Depp and Winona Ryder
According to Johnny Depp, when it came to Winona Ryder, it was love at first sight. The two met at a premiere in 1989 when Depp was 26.
Ryder was 17 at the time. Despite quickly falling in love, the two only began officially dating about four months after Ryder’s 18th birthday.
Five months later, they were engaged. Depp famously got a tattoo of the actress’s name to mark his love.
He then altered that tattoo to say ‘Wino forever’ after the two ended their engagement three years later.
Don Johnson and Melanie Griffith
Way back in 1972, 22-year-old Don Johnson met the daughter of his costar Tippi Hedren, 14-year-old Melanie Griffith, and fell in love.
The two very quickly became attached, and by the time Griffith had turned 15, they had moved in together.
On her 18th birthday, Johnson proposed. They married in 1976, but less than a year later, they divorced.
After several other failed relationships, the two rekindled their romance and remarried in 1989, which soon led to the birth of Dakota Johnson.
Five years later, they split for good but still remain close.
Bill Wyman and Mandy Smith
When Bill Wyman was 47, the ex-member of Rolling Stones was the subject of quite a controversy. In 1984, he met Mandy Smith, who was just 13 at the time.
It’s unclear how romantic their relationship was at the time.
Their relationship became public when she turned 16, and in 1989, when Smith reached the age of 18, the two were married.
In his 1990 autobiography, he wrote, “She took my breath away…she was a woman at 13.” They divorced just two years later.
Dane Cook and Kelsi Taylor (26 Years)
Dane Cook is a pretty popular comedian who likes to keep things on the edge. Maybe that’s why he opted to go for a younger woman, Kelsi Taylor, when he began dating.
However, it seems to be working because they’ve been together for quite a while.
After initially meeting each other at a game night at Cook’s house, the two quickly developed a relationship, and even with a 26-year age gap, they still have a lot in common.
David Foster and Katherine McPhee (34 Years)
There are lots of great stories when it comes to romantic entanglements, and how a couple meets. David Foster and Katharine McPhee first met when Katharine was a contestant on the fifth season of American Idol.
Because Katharine was going to be performing a song that was originally written by David, he stopped by to help her practice.
With David as her mentor, the two developed a friendship and eventually, in 2018, announced their engagement.
Of course, the media focused on their 34-year age gap rather than the relationship itself.
P. Diddy and Lori Harvey (28 Years)
Sean Combs has been in showbiz for decades, and because of this, he has been attached to several high-profile relationships with the likes of Jennifer Lopez.
One of the longest, though, was with the singer Cassie.
When this relationship eventually fell apart, the entrepreneur began dating Lori Harvey. The two had a 28-year age gap, and that may be why the relationship only lasted three months.
Wilmer Valderrama and Demi Lovato (12 Years)
The relationship is long over, but it seems that Wilmer Valderrama has a thing for younger women. In the past, his preferences gained a lot of attention, especially when it came to his six-year relationship with singer Demi Lovato.
With a 12-year age gap, the couple still seemed to be able to manage their differences. However, the two broke up eventually and moved on with their lives.
Today, Wilmer is engaged to Amanda Pacheco — with whom he shares a child.
Sylvester Stallone and Jennifer Flavin (22 Years)
Hearing Sylvester Stallone’s name automatically conjures up images of a sweat-clad boxer punching a slab of meat.
Perhaps his most iconic role, Rocky, also introduced him to his sweetheart — who he’s been with for over two decades!
Stallone met wife Jennifer Flavin on the set of Rocky V when he was 42, and she was 19. After 24 years together, they seem to have absolutely no issues with their 22-year age gap.
Mel Gibson and Rosalind Ross (35 Years)
Though Mel Gibson has had some pretty controversial moments over the past couple of decades, he’s still one of the most iconic actors in Hollywood.
Because of his place in the entertainment industry, any relationship he has gains a lot of attention.
That includes his relationship with Rosalind Ross, who is 35 years younger than him. This large age gap could be a problem for some, but it doesn’t seem to be for them.
Hollywood has no shortage of age-gapped relationships, where one person is a lot older than their romantic partner.
In the case of some relationships, the difference between ages was especially extreme, bringing with it quite a bit of criticism for the couples in question.
Take a look at these relationships, which made headlines and caught lots of attention in Hollywood.