Cradle-Robbing Celebrities

Hugh Hefner was engaged to 24-year-old Crystal Harris until she canceled the wedding. Now she says sex with the 85-year-old Playboy founder lasted "like two seconds." But Hef tweeted: "Crystal lied about our relationship." Hef had ended a relationship with 20-year-old twins to settle down with Harris, a December 2009 Playmate.

Image 1 of 59 Getty Images
    • heffwife.B.jpg
    • hefner_Shera Bechard.jpg
    • 117362283.jpg
    • hughhef.jpg
    • jlodatingsmart1.jpg
    • 0706_GeorgeElisabetta.jpg
    • jonas_ Goodrem.jpg
    • 070511 al pacino Lucila Sola.jpg
    • 070511 alec baldwin hilaria thomas.jpg
    • 115254157.jpg
    • taylorwood_johnson.jpg
    • jefflydiasplit.jpg
    • jeffkrissplit.jpg
    • jefftaniasplit.jpg
    • doug hutchinson.jpg
    • 114517379.jpg
    • lorenzo_lamas_050211.jpg
    • 1145131743.jpg
    • scar_penn_722.jpg
    • 121610RonWood01.jpg
    • 0727_linda_hogan.jpg
    • 081910SNL01.jpg
    • tom-cruise-katie-holmes.jpg
    • 043011 carey cannon.jpg
    • 0702PaquinMoyer.jpg
    • 11.27-megan-fox-disney.jpg
    • 0706MadonnaJesus.jpg
    • 0706perrybrand.jpg
    • 0702Marilyn.jpg
    • 0706matthewcamilla.jpg
    • logan2.jpg
    • 0702haydenp.jpg
    • 0706emmyrossum.jpg
    • evalongoria1.jpg
    • 0706melgibson.jpg
    • 0702KingSouthwick.jpg
    • judesienna.jpg
    • 0706DemiAshton2.jpg
    • ccarquette.jpg
    • kim1.jpg
    • murdoch1.jpg
    • 0706_AllenSoonYi.jpg
    • 082009-hookup-goldblum-raimonde.jpg
    • 0706_NickCage.jpg
    • 0706DouglasZeta1.jpg
    • 0706FlockhartFord.jpg
    • 0706AnistonMayer.jpg
    • 0706aubryberry.jpg
    • 0706sarandonrobbins.jpg
    • naveen.jpg
    • trump4.jpg
    • jameswoods.jpg
    • geena.jpg
    • olivanjohn.jpg
    • sheryl.jpg
    • ellen19.jpg
    • marytylermoore1.jpg
    • billy_joel_katie_lee.jpg
    • mick_jagger_scott.jpg
Replay Slideshow

Cradle-Robbing Celebrities

It seems like a necessary stop on the path of a Hollywood starlet: move to LA, go on auditions and date a man your father's age. Here are a few of our favorite celebrity couples who think age ain't nothing but a number.

Please wait. Your gallery will be ready in 5 seconds.

Leave Comments
Don't Miss

local

Feb 14, 2012

Another Philly Cop Arrested: Police

This is the 40th Philadelphia Police officer to be arrested since 2009

local

17 minutes ago

Houston Plans Shift: No Public Memorial

Whitney Houston will be laid to rest after a private, invitation-only funeral at her...

local

4 minutes ago

Police Seek High-Risk Homeless Sex Offender

James E. Fleetwood, 29, is a high-risk sex offender who never registered, police say

local

3 hours ago

Man Arrested for Power Station Copper Thefts

Police sat they found about $1,500 in stolen copper in suspect's vehicle.