Hollywood Men Who Dated Much Younger Women

HILARY DUFF AND JOEL MADDEN (2004-2006)

Most articles about this couple back in the day were either screaming "omg couple goals" or stating they were an interesting pair due to Hilary's "good girl" image and Joel Madden being a "bad boy." But what was really messed up was that Joel was 24 YEARS OLD and Hilary was only 16.

 

WILMER VALDERRAMA AND...WELL EVERYONE

Wilmer is notorious for dating much younger women:

  • he dated Lindsay Lohan when she was 17 and he was 24
  • he dated Demi Lovato when she was 17 and he was 29
  • he dated Mandy Moore when she was 16 and he was 20
 

TYGA AND KYLIE JENNER (2014-2017)

Right before Kylie started dating Travis Scott, she dated Tyga for 3 years...he was 25, she was 17.

 

R. KELLY AND AALIYAH (1994-1995)

This is just the tip of the iceburg for R. Kelly's issues but back in the mid-90's, he married 15-year-old Aaliyah...on their marriage certificate, her age was listed as 18. R. Kelly was 27.

 

MILO VENTIMIGLIA AND HAYDEN PANETTIERE (2007-2009)

Jack Pearson would never! But Milo would - he dated Heroes co-star Hayden Panettiere for two years when she was 17 and he was 29.

 

PAUL WALKER AND JASMINE PILCHARD-GOSNELL (2006-2013)

A 33-year old Paul Walker started dating 16-year-old Jasmine Pilchard-Gosnell in 2006 and they remained together until his death in 2013. She was only 8 years older than Walker's daughter, Meadow.

 

JAY-Z AND BEYONCE (1999-PRESENT)

They've been hailed as such a power couple for so long that many people forget that Beyonce was only 18 Jay-Z was 30 when they started dating...allegedly.

 

ELVIS PRESLEY AND PRISCILLA PRESLEY (1967-1973)

YUP even the King! Elvis was 25 when he met his future wife Priscilla. She was 14. They went on to date for 7 years before getting married.

 

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