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.
Joel Madden and Hilary Duff
Joel Madden, the lead singer of the band Good Charlotte, was 25 years old when he met 16-year-old teen star Hilary Duff in the summer of 2004. After many speculations on social media, Susan Duff publicly announced her daughter and Madden were dating in 2005.
The relationship didn’t last long, and in 2006 the two split up. A month later, Madden began dating Nicole Richie. The two are still married and have two children together. Since their split, Duff has gotten married, divorced, and married again.
Jerry Seinfeld and Shoshanna Lonstein
At the height of Seinfeld‘s success in 1993, then 38-year-old Jerry Seinfeld met high school senior Shoshanna Lonstein in Central Park. After exchanging numbers, the 17-year-old began dating the seasoned comedian.
The two dated for four years, with Lonstein even transferring to UCLA to be close to Seinfeld. The two were the subject of media scrutiny and criticism during their time together. They finally broke up in 1998. Seinfeld met his wife, Jessica Sklar, that same year.
Doug Hutchison and Courtney Stodden
When non-binary model Courtney Stodden had just turned 16, 50-year-old seasoned actor Doug Hutchison talked to their mother and asked if he could become Stodden’s acting couch. He then asked their mother for approval to marry the model.
Just a week after meeting face to face, they got married. Although Stodden attempted to leave the marriage twice before, it was only in 2018 that they filed for divorce. Their divorce was finally official two years later.
Jerry Lee Lewis and Myra Gale Brown
Throughout the life of legendary rock & roll musician Jerry Lee Lewis, he was married seven times. Many of his relationships were controversial. Most relevant here was his marriage to his 13-year-old cousin, Myra Gale Brown, in 1957.
The two had their first child together when Brown was 14. The boy later passed away in a tragic accident. Their daughter was born in 1963. In 1970, Brown filed for divorce, sharing in her statement that she had been “subject to every type of physical and mental abuse imaginable.”
Fergie and Justin Timberlake
It’s not just male rock & rollers who date younger people. Fergie was also involved in such a relationship with Justin Timberlake. When the two were dating, the Black Eyed Peas singer was 23, while Timberlake was 16.
After the two broke things off, Fergie shared in an interview, “Justin and I would go out together and have fun and make out.” Through the years, she continued to explain that it was nothing serious.
Elvis Presley and Priscilla
This couple might be the most famous age-gap Hollywood couple ever. As the story goes, during his service, 24-year-old Elvis Presley met 14-year-old Priscilla Beaulieu and fell in love. At first, the relationship was long distance.
Once he returned home, their romance strengthened. At 16, Priscilla moved to Memphis to be closer to the star. Finally, in 1967, when Pricilla was 21, the two married. They had Lisa Marie just a year later. The two finalized their divorce in 1973.
Steven Tyler and Julia Holcomb
Aerosmith’s legendary lead singer, Steven Tyler, had his own news-worthy relationship at the age of 26, back in 1973. After a concert, Tyler met his 16-year-old fan, Julia Holcomb. According to a source, the two were “captivated” with each other right away.
Shortly after, Holcomb’s mother signed guardianship over to Tyler so that Julia could join Aerosmith on tour. He continued to be her legal guardian for the entirety of their relationship. The two finally separated in 1977 after a failed pregnancy.
Chad Michael Murray and Kenzie Dalton
In 2006, then-25-year-old Chad Michael Murry met 17-year-old Kenzie Dalton on the set of One Tree Hill. The actor had just split up with Sophia Bush when he began dating Dalton.
In 2006, Murray and Dalton got engaged, with the young woman still a high school senior — and only eight months after that, Murray and Bush were officially divorced. Murray and Dalton remained engaged for seven more years, finally calling it quits in 2013.
Prince and Mayte Garcia
Prince and Mayte Garcia met for the first time in 1990 when the then-16-year-old dancer was auditioning to be part of the then-32-year-old star’s tour. At 17, Prince became Garcia’s legal guardian, allowing her to come with him to the US.
Their explicitly romantic relationship officially began when Garcia turned 19. They married on Valentine’s Day in 1996. During their marriage, they lost their child shortly after birth. After a failed pregnancy, the two finally broke things off and divorced in 2000.
Tyga and Kylie Jenner
In 2011, Tyga was invited to perform at Kendall Jenner’s Sweet 16 party, where he met young Kylie Jenner. Reportedly, the rapper began dating Jenner when she turned 17, in 2014 (he was 24 at the time).
Official news of the romance came out only a year later, after Jenner’s 18th birthday. In 2017, they split. In an interview, Jenner explained why they broke up, saying, ”There was no crazy fight, we just decided…Well, I decided that I’m really young.”
Leonardo DiCaprio and Gisele Bündchen
Leonardo DiCaprio is famous for never having a girlfriend over 25. During his first famous relationship, though, he was 24. His girlfriend at the time, Gisele Bündchen, was 18 years old. The two began dating in 1999.
They were in an on-and-off relationship for six years. But, by 2005, they broke things off officially. Years later, Gisele explained that one of the reasons they broke up was her wish to change, which wasn’t shared by him.
Jimmy Page and Lori Maddox
Lori Mattix (Maddox) was first introduced into the world of rock & roll when she was just 13, soon becoming a popular teen model. After seeing a picture of the teen, Led Zeppelin’s Jimmy Page reportedly fell in love with her.
After avoiding meeting him several times, Page’s manager brought the then-14-year-old to the rockstar’s room, and they began their relationship. Though they were apparently madly in love, after Maddox turned 16, Page left her for Bebe Buell. They dated again briefly in the ‘80s but quickly ended things once and for all.
Luc Besson and Maïwenn Le Besco
The famed director of La Femme Nikita, Luc Besson, met Maïwenn Le Besco in 1991 — shortly after divorcing his first wife, Anne Parillaud. At the time, Besson was 31, and Maïwenn was 15 years old.
They married just a year later when Le Besco became pregnant at 16. Their daughter, Shanna, was born in 1993. The marriage ended after Besson began an affair with Milla Jovovich while the two were filming together.
Wilmer Valderrama and Demi Lovato
Former That ‘70s Show star Wilmer Valderrama, then 29 years old, met 17-year-old Demi Lovato in 2010 after filming a PSA together. The musician shared years later that they signed on for the PSA to meet Valderrama, thinking “he was really cute.”
Apparently, it was “love at first sight” for the two. But, the musician explained that they only began dating once she turned 18. After six years together, the two released a statement on Instagram sharing with fans that they had decided to break up.
Anthony Kiedis and a Fan
This one is quite controversial. Per his admission, during a tour when he was in his mid-20s, Anthony Kiedis from the Red Hot Chill Peppers spent the night with a fan. She then traveled with them the next day to their next venue.
It was then that she let him know she was a 14-year-old runaway from Louisiana and her father, the chief of police, was conducting a search since she had gone missing. It was then that Kiedis knew he needed to get her home, but not before spending one more night with her.
Charlie Chaplin and Lita Grey
Lita Grey met comedic legend Charlie Chaplin when she was just eight years old. She then worked with him on The Kid in 1921. However, their relationship only began when they met again when she was 15 on the set of The Gold Rush.
Chaplin was 35 when they began their affair in 1925. After Grey found out she was pregnant, the couple married in secret to avoid Chaplin being persecuted. They had two sons together, just 10 months apart. Reportedly, Chaplin was never faithful, and they divorced in 1927.
Ted Nugent and Pele Massa
In 1978, Guitarist and singer Ted Nugent met 17-year-old Pele Massa in Hawaii. The singer, then 30, wished to get married to Messa but due to the laws of the state, they couldn’t until she would be older.
In a Behind the Music documentary, Nugent said that he got permission from Massa’s parents to legally adopt her. However, no evidence has been shown to corroborate this statement which he later denied. The two were together for seven years.
Claude Francois and France Gall
French singer Claude François was involved with Eurovision winner, France Gall, around the time she won the international music competition. At the time, Claude was dealing with the aftermath of his failed marriage to Janet Wollacoot, who left him in 1962.
When François and Gall began their relationship, she was 17 years old, and he was 25. By 1967, two years after beginning their romance, they broke up.
Zach Braff and Florence Pugh
Zach Braff first approached (via social media) Florence Pugh in 2018 when she was 22 years old and he was 43 years old. The next year rumors began that the two were dating, which was soon confirmed by the couple.
During their relationship, Braff and Pugh were a favorite paparazzi subject, though they were also happy to share their relationship with their fans on social media. They also adopted a dog together in 2020. In the summer of 2022, they shared that they broke up.
Marvin Gaye and Janis Hunter
In 1973, Marvin Gaye (aged 34) was working on his album Let’s Get it On in Los Angeles when he met 17-year-old Janis Hunter. The two began dating soon after. Gaye’s song “Jan” was a tribute to Hunter. The two married in 1977.
Gaye was 38, and Hunter was 21 on their wedding day. As revealed later in Hunter’s book — After the Dance: My Life With Marvin Gaye — the relationship was turbulent, and the two divorced three years later. Gaye passed away just three years after that.
Rick Springfield and Linda Blair
Linda Blair found massive fame at the age of 15 when she starred in The Exorcist in 1973. Around the time the film became a huge success, Blair met Australian singer Rick Springfield.
Springfield was 25 years old when the two met at a concert at Whisky a Go Go. The musician was quoted saying that Blair was the “hottest young actress in movies.” The relationship was scrutinized by the media, and they broke up fairly quickly. They still remain friends.
Nicole Scherzinger and Harry Styles
Before Harry Styles became famous as a solo artist, he was a key member of One Direction. The group was created in 2010 on The X Factor. On the same show a few years later, he met show judge Nicole Scherzinger of the Pussycat Dolls.
In 2014, the two met again and began dating. Styles was 19, and Scherzinger was 35 years old at the time. The fling, however, was short-lived and they quickly broke things off.
John Mayer and Taylor Swift
Thanks to her songs, Taylor Swift’s exes have become infamous. One of the most notable is “Dear John”, which seems to have been based on Swift’s short relationship with fellow musician John Mayer in 2009.
At the time of their relationship, Swift was 19 years old and Mayer was 32. Although during their time together, they collaborated professionally, the two have written multiple scathing songs about each other since their break up in 2010.
Madonna and Jesus Luz
Madonna has become known for dating younger men. At the age of 49, shortly after her divorce from Guy Ritchie was finalized, the megastar began dating 21-year-old Brazilian model Jesus Luz.
The couple enjoyed two years together before parting ways in 2010, claiming the split was due to their 28-year age difference and the fact that they had nothing in common. Reportedly, it was Luz who initiated the breakup.
Demi Moore and Ashton Kutcher
Demi Moore and Ashton Kutcher’s eight-year relationship created quite a media frenzy around it. The actors met in 2003 as Kutcher was making a name for himself on That ‘70s Show. Just two years later, they got married.
The couple never shied away from their 15-year age gap, often joking about it. The relationship, however, didn’t last — they separated in 2011 after being married for six years. Kutcher began dating Mila Kunis in 2012. Kutcher and Moore’s divorce was finalized in 2013.
Wilmer Valderrama and Lindsay Lohan
Wilmer Valderrama and Lindsay Lohan’s relationship was pretty whirlwind. The two met in 2004, with Valderrama at the height of That ‘70s Show’s success and Lohan fresh off Mean Girls.
Lohan had just turned 18, and Valderrama was 24. The two actors tried their best to keep their relationship private. After two months of dating, the couple got engaged. Two months after that, however, they broke up.
The Weeknd and Bella Hadid
Abel Tesfaye — a.k.a. the Weeknd — and Bella Hadid’s relationship has had quite a few ups and downs. The two celebs began a relationship in 2015, with Hadid aged 18 and the Weeknd then 25. A year later, they amicably split.
In 2018, however, after the musician broke things off with Selena Gomez, the two got back together, even celebrating Hadid’s 22nd birthday together and uploading loving posts about each other on social media. In 2019, they broke up again.
Jay-Z and Beyoncé
Beyoncé was 18 the first time she met who would become her husband, Jay-Z. After being seated next to each other on a plain in 2000, the two began a friendship, often talking on the phone. They began a romantic relationship, however, only a year later. Jay-Z was about 31.
From then on, they were inseparable. In 2008, they tied the knot in a secret ceremony, hidden from the paparazzi. In 2011, Beyoncé famously revealed her pregnancy during the VMAs. The two share three children — Blue Ivy and twins Sir and Rumi.
Wanya Morris and Brandy
Moesha star Brandy fell in love in the early ‘90s with Wanya Morris, the singer from Boyz II Men. According to him, Brandy’s mother brought her to his attention as she was looking for a mentor for her daughter.
The two spent a lot of time together when Brandy was 17, and once she turned 18, they began a romantic relationship. Brandy was quoted calling Morris her “first love.” In 1998, however, they broke things off. Morris was about 25 by then.
Henry Cavill and Tara King
Shortly after ending his relationship with MMA fighter Gina Carano in 2015, Henry Cavill fell in love with 19-year-old college student Tara King. Cavill was 32 when they began dating.
In interviews at the time, Cavill spoke very highly of his girlfriend. However, the romance was short-lived, as a source explained that ”she was in too deep, and he didn’t want anything too serious.” They did remain friends for a short time after breaking up.
Taylor Swift and Conor Kennedy
One of Taylor Swift’s shortest relationships happened during the summer of 2012 when she became close to the Kennedy family. During an event at the family’s compound, she got to meet young Conor Kennedy, who was 18 at the time, while Swift was 22.
The two spent much of that summer together, with Swift providing Kennedy a shoulder to cry on after a family tragedy. By September, however, the two quietly went their separate ways. A source shared that the split was amicable.
Woody Allen and Babi Christina Engelhardt
Woody Allen and Babi Christina Engelhardt met in 1976 when the then-16-year-old slipped her phone number on Allen’s table in a restaurant. They began a secret relationship. The then-41-year-old director reportedly never asked for her age, only knowing that she was in high school.
They continued their undercover relationship for eight years. During that time, Allen filmed the controversial film Manhattan in which a similar relationship is depicted. Opening up years later, Engelhardt explained her perspective — “This made me who I am. I have no regrets.”
Wilmer Valderrama and Mandy Moore
From 2001 to 2002, Wilmer Valderrama dated then-16-year-old Mandy Moore. They met a year before during a photoshoot for a teen magazine, Moore shared in an interview in 2018.
The old romance hit the gossip columns again in 2005 when Valderrama made a careless comment about his intimate relationship with Moore which deeply hurt the young actress. In her own interview, she explained that it was false. Valderrama later apologized and tried to rescind the comment, The two are still friendly.
Cheryl Cole and Liam Payne
Liam Payne of One Direction fame first met Cheryl Cole when he auditioned for The X Factor, where she was a judge. He was 14, and Cheryl was 24. They started dating in 2016 after Liam had turned 22.
The next year the two welcomed their baby boy, Bear Grey. Only a few months later, however, the two broke up. The two still co-parent their kid as friends.
Dane Cook and Kelsi Taylor
Dane Cook’s engagement to Kelsi Taylor in 2020 made headlines due to their 26-year age gap. It was later revealed that the two met for the first time in 2016 at one of Cook’s famed house parties when Taylor was 17.
She was 18 when they officially began dating, Cook was 45 at the time. Now over 50, the comedian proposed to Taylor in 2022, and the two seem to be looking forward to getting married and starting a family.
René Angélil and Celine Dion
38-year-old René Angélil met musical prodigy Celine Dion back in 1980 when she was 12 years old. After she auditioned for him, he became her manager. After working together for seven years, the two went on their first date when Dion was 19.
They got engaged in 1991 after the international success of Dion’s first English album. They kept their relationship fairly quiet for quite a few years until announcing it in 1993 and marrying soon after. They had three kids and were together until Angélil’s passing in 2016.
Scott Disick and Sofia Richie
Reality star Scott Disick met then-19-year-old Sofia Richie in 2017. Rumors about them first began when the two were pictured celebrating Disick’s 34h birthday on a yacht. Just a few months later, the relationship was confirmed.
Both the Kardashians (close to Disick) and Lionel Richie (Sofia’s father) expressed their criticism of the relationship on air. Although there were rumors on and off that they were broken up at times, the couple ended up staying together for three years. They finally broke up in 2020.