Random Older Celebrities Who Actually Dated Teenagers (20 items)

(#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.
(#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.
(#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.
(#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.
(#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.
(#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.