Last week, former Beatle Paul McCartney, 68, announced his engagement to Nancy Shevell, his girlfriend of four years. McCartney has been down the aisle before. The same is true for the elder half of most of the May-December romances featured in this slideshow.
Hugh Hefner, 85, used his Twitter account to announce his engagement to much, much younger Playmate Crystal Harris on Christmas Eve
Oscar winners Michael Douglas, 66, and Catherine Zeta-Jones have two kids together. Zeta-Jones stuck by Douglas during his cancer battle and now he's standing by her side as she wages a high-profile struggle with mental illness
Oscar winner Susan Sarandon and documentary filmmaker Jonathan Bricklin, who's in his early 30s, haven’t confirmed their relationship status, but the pair has been spotted around the world.
The Peruvian-born theater manager, who's in his early 40s, is the fifth husband for the former "Dynasty" star
The departing "CBS Evening News" anchor began dating triathlete Brooks Perlin, 37 several years after her husband died.
Who ever would have guessed that Indiana Jones and the 46-year-old actress who played Ally McBeal would end up together?
Director Sam Taylor-Wood, 44, and actor Aaron Johnson had their first child together last year.
Larry King, 77, and his wife, Shawn, called off their divorce last year and seemed to be a happy family during the host’s last CNN show
Some think the 56-year-old action star’s young wife bears a striking resemblance to his first wife.
Rocker Rod Stewart, 66, and his model wife welcomed their second child in February.
Despite their rocky beginnings, Woody Allen, 75, and Soon-Yi Previn went on to adopt two daughters and are still together today.
Guitar legend Eric Clapton, 66 tied the knot with young graphic artist Melia McEnery in a surprise ceremony.
Congressman Dennis Kucinich, 64, and his statuesque British wife turn plenty of heads when they’re on the campaign trail
Former Speaker of the House Newt Gingrich, 67 married his younger wife, Callista in 2000. They began dating her while he was still married to his second wife.
Speaking of possible presidential contenders, the star of "The Apprentice" and Slovenian model Melania Trump, now 41, married in 2005 and had a son in 2006.
Former presidential candidate Fred Thompson, 68, and star of a long-running prime-time drama married his much younger political consultant wife in 2002.
Rush Limbaugh and Kathryn Rogers
Conservative radio talk show host Rush Limbaugh, 60, and his new bride, who's in her early 30s, began dating a few years after he divorced his second wife.
Netscape founder Jim Clark, 67, and Sports Illustrated swimsuit model Kristy Hinze were married in 2009.
Oscar winner and tango fanatic Robert Duvall, 80 met his much younger Argentinean actress wife in Buenos Aires.
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