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

4 hours ago

Houston Toxicology Too Technical to Rush

The 411 on why Whitney Houston's toxicology results may take weeks to process.

local

38 minutes ago

President Obama to Arrive in LA Wednesday

President Obama is expected to attend a variety of re-election fundraisers during a...

local

4 hours ago

3 Marines Killed in Dana Point Crash

Three U.S. Marines were killed and a fourth was injured in a crash near Dana Point...

cars

32 minutes ago

California Might Consider Hybrid Settlement

The settlement prompted one hybrid owner to pursue her case against Honda in small...