Random Older Celebrities Who Actually Dated Teenagers (20 items)

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  (#1) Elvis Presley

  • Dec. at 42 (1935-1977)

  Priscilla Presley, who turned 77 in 2022, was only 14 when she met 25-year-old Elvis at a party in Bad Nauheim, Germany. She was the daughter of a US Naval pilot, and Presley was serving in the Army despite a successful music career. Priscilla's parents pressured the two to marry, and they tied the knot in 1967 when she was 21.

  While even diehard Elvis fans have a hard time with the initial age gap, Priscilla maintains the two waited to consummate the marriage until their wedding night. They had one daughter, Lisa Marie, and amicably divorced in 1973.
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  (#2) R. Kelly

  • 56

  R. Kelly has faced a great deal of scrutiny for his actions with underage girls. In 2022, Kelly was sentenced to 30 years in prison by a federal judge for crimes including sex trafficking, child racketeering, and sexual exploitation of a child.

  Before being convicted, in the '90s, he had a relationship with up-and-coming R&B singer Aaliyah. Kelly was introduced to Aaliyah as a "mentor," and he helped write and produce her first album, Age Ain't Nothing But A Number, when she was 14.

  Despite denials from both parties who claimed that their relationship was platonic, the two secretly wed in 1994. The marriage was ultimately annulled as Aaliyah was not yet old enough to consent to a lifetime with the 27-year-old Kelly. Tragically, she passed away in a plane crash in 2001.
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  (#3) Dane Cook

  • 51

  Comedian Dane Cook found love with a much younger partner when he began dating 19-year-old Kelsi Taylor in 2017. The two connected through mutual friends and seemingly bonded over their shared love of music, as Taylor is a singer-songwriter herself. Cook wasn't shy about sharing their relationship on social media, often posting photos of their vacations and date nights. Despite the age difference, the couple appeared to be going strong for quite some time, but they eventually went their separate ways.
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  (#4) Scott Disick

  • 40

  Reality TV star Scott Disick, best known for his role in Keeping Up with the Kardashians, raised eyebrows when he began dating 19-year-old Sofia Richie in 2017. The pair initially met during a vacation in the South of France and kicked off their romance soon afterward. During their relationship, Disick and Richie often traveled together and shared their experiences on social media, despite facing criticism for their substantial age difference. However, in 2020, after nearly three years together, the couple called it quits.
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  (#5) Jerry Seinfeld

  • 69

  At the height of his Seinfeld fame in 1993, Jerry Seinfeld approached Lonstein, then a 17-year-old high school student, walking around in Central Park. After getting Lonstein's number, the pair started dating quite seriously despite the age difference (Seinfeld was 38 at the time). Lonstein was a senior, and the two continued dating for the four years she attended college.

  Seinfeld spent much time defending their relationship, but the two split for good in 1997. Shortly thereafter, Seinfeld met his current wife, Jessica Sklar. The pair have been married for more than 20 years.
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  (#6) Wilmer Valderrama

  • 43

  It might just be easier to list the celebrity teens Wilmer Valderrama hasn't dated. He dated 16-year-old Mandy Moore from 2001-2002 despite being four years her senior. At age 24, Valderrama dated 17-year-old Lindsay Lohan, though they kept the relationship a secret until her 18th birthday in 2004. They broke up a year later, inspiring her broken-hearted song, "Over."

  Then in 2010, the 30-year-old began dating 17-year-old Demi Lovato. The two have been on and off since then but are currently off, with it highly unlikely that they will rekindle their romance. 
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  (#7) Luc Besson

  • 64

  After his 1991 divorce from Nikita star Anne Parillaud, director Luc Besson, 32, started dating 15-year-old Maïwenn Le Besco. The couple married the following year while Maïwenn was pregnant with their daughter. Besson later claimed that their relationship inspired his film Léon: The Professional (1994), which followed an emotional relationship between an adult man and a young girl.

  Besson and Le Besco were married until 1997 when he became involved with The Fifth Element actress Milla Jovovich, who was in her early twenties at the time. Besson and Jovovich were married from 1997 until 1999, when they divorced. 
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  (#8) Taylor Swift

  • 33

  Pop sensation Taylor Swift had a brief relationship with 17-year-old Conor Kennedy, grandson of Robert F. Kennedy, in the summer of 2012. The duo was introduced by mutual friends and quickly became inseparable, often seen together at various Kennedy family events in Cape Cod. Swift even penned a song about their whirlwind romance, titled "Begin Again." However, the pair's relationship fizzled out as quickly as it began, and they split later that same year.
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  (#9) Robin Thicke

  • 46

  Back in 2014, amidst his public divorce from actress Paula Patton, singer Robin Thicke began dating 19-year-old model April Love Geary. The pair met at a party and hit it off immediately, despite the nearly 20-year age gap between them. Thicke and Geary were often seen traveling together and attending industry events hand-in-hand. As of 2021, the couple is still together and even welcomed three children into the world.
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  (#10) John Mayer

  • 45

  When 19-year-old Taylor Swift began dating 32-year-old John Mayer in 2009, the world did a collective head scratch. Less than a year later, Swift released the song "Dear John" on her album Speak Now, which not-so-subtly panned Mayer with lyrics including, “Don't you think 19's too young to be played / by your dark twisted games / when I loved you so?”

  Never one to remain silent, Mayer clapped back in a Rolling Stone interview, saying it was a humiliating and lousy thing for her to do to him. 
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  (#11) Joel Madden

  • 44

  In 2006, Good Charlotte frontman Joel Madden began dating teen star Hilary Duff when she was just 16 years old, and he was 25. The couple first met on the set of MTV's TRL and maintained a relatively low-key relationship for nearly two years. Although they faced criticism for their age gap, Madden and Duff continued to date until 2008 when they ultimately decided to part ways. Both have since moved on, with Madden marrying actress Nicole Richie, and Duff marrying musician Matthew Koma.
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  (#12) Kobe Bryant

  • 45

  The Bryants have dealt with quite a few relationship headlines in the media, so the fact they met when Vanessa was only 17 is probably the least of their concerns. When the basketball star was 21 years old, he met Vanessa while she was working as a backup dancer for a music video.

  Six months later, the two got engaged, and they tied the knot sans prenup when she was 18 years old. Despite nearly breaking up on several occasions, the two persevered until, sadly, Bryant and their daughter Gianna died in 2020 and left his wife with three living children.
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  (#13) The Weeknd

  • 33

  Singer-songwriter The Weeknd, whose real name is Abel Tesfaye, made headlines when he began dating 18-year-old model Bella Hadid in 2015. The pair initially met while working on the set of one of The Weeknd's music videos, and their relationship quickly blossomed. In their time together, they attended numerous high-profile events, including the Met Gala and New York Fashion Week. Despite an on-again, off-again relationship spanning several years, Tesfaye and Hadid ultimately called it quits for good in 2019.
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  (#14) Nick Lachey

  • 49

  While most people remember this couple for their post-marriage show, The Newlyweds, not many people recall that when these two met in 1998, Lachey was 25 and Simpson was 18.

  As we all know by now, Lachey and Simpson's three-year marriage ended in divorce in 2005.
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  (#15) Tyga

  • 33

  The rapper and the youngest member of the Kardashian reality clan Kylie Jenner began "hanging out" an awful lot beginning in 2014 when she was 16, and he was 24. They dated on and off for a few years, though they became a lot more "on" after Jenner's 18th birthday in August 2016.

  Tyga caught a lot of heat for the relationship, not only from the public but from the mother of his son, Blac Chyna. The two split for good in April of 2017. Shortly after, Jenner gave birth to daughter Stormi with rapper Travis Scott in 2018.
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  (#16) Chad Michael Murray

  • 42

  Kenzie Dalton lived out every high schooler's dream when 25-year-old television star Chad Michael Murray proposed to her in 2006. Literally - because she was still a senior in high school. Murray met Dalton after she appeared as an extra on One Tree Hill.

  Before ultimately parting ways, the pair remained engaged for seven years - incidentally the same number of years as their age gap.
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  (#17) Doug Hutchison

  • 63

  Courtney Stodden and Doug Hutchison have made plenty of headlines for their cross-generational romance, particularly when then 16-year-old Stodden married the 51-year-old actor in Vegas after meeting him online. She needed parental permission to get married, a move her now-estranged "momager" says she regrets.

   

  The unlikely duo had been through many ups and downs, including a trial separation, a stint in Couples Therapy, and a miscarriage, but ultimately decided to divorce in 2020.
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  (#18) Sam Taylor-Johnson

  • 56

  British filmmaker Sam Taylor-Johnson's relationship with now-husband Aaron Taylor-Johnson raised eyebrows when they started dating in 2009 while Taylor-Johnson was just 18 years old, and Sam was 42. The couple met on the set of Nowhere Boy, which Sam directed, and began dating after the film wrapped. Despite facing criticism for their 24-year age gap, the duo married in 2012 and have since welcomed two children together. They continue to be a strong couple in Hollywood and have often spoken out about their unwavering love and support for one another.
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  (#19) Don Johnson

  • 73

  In the early '80s, actor Don Johnson had a brief yet notable relationship with then-14-year-old actress Melanie Griffith. The two met while Johnson was living with Griffith's mother, actress Tippi Hedren, and they began dating when Griffith was just a teenager. The couple eventually married in 1976 when Griffith was 18 years old but later divorced in 1978. Surprisingly, they remarried in 1989 and welcomed daughter Dakota Johnson into the world before ultimately divorcing again in 1996.
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  (#20) Justin Gaston

  • 35

  Model and musician Justin Gaston gained public attention when it was revealed that he was dating a then-15-year-old Miley Cyrus in 2008. The couple met while Gaston was working as a contestant on the reality show Nashville Star, which Miley's father, Billy Ray Cyrus, was hosting. Despite their 5-year age difference, Cyrus and Gaston frequently attended events together and were often seen out on the town. However, their relationship was short-lived, and they split up later that year.

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