Pursue Love Deliberately!

1 Year

Tony Blair . . . Cherie Booth
James Brolin . . . Barbra Streisand
Bill Clinton . . . Hilary Clinton (Hilary Rodham Clinton)
Sean Connery . . . Micheline Roquebrune
David E. Kelley . . . Michelle Pfeiffer
Paul McCartney . . . Linda (McCartney (Linda Eastman)
Al Pacino . . . Beverly D'Angelo
Freddie Prinze Jr. . . . Sarah Michelle Geller
Brandon Routh . . . Courtney Ford
Frank Sinatra . . . Nancy Barbato
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2 Years

Merve Adelson . . . Barbara Walters
Phil Donahue . . . Marlo Thomas
King Edward VIII . . . Wallis Simpson
Gavin Rossdale . . . Gwen Stefani
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3 Years

Prince Ernst August . . . Princess Caroline of Monaco
Tom Brady . . . Gisele Bündchen
Garth Brooks . . . Trisha Yearwood
Matthew Broderick . . . Sarah Jessica Parker
Sean Connery . . . Diane Cilento
Stedman Graham . . . Oprah Winfrey
Robert F. Kennedy . . . Ethel Skakel
Ozzie Nelson . . . Harriet Hilliard
Barack Obama . . . Michelle Robinson
Ronald Reagan . . . Jane Wyman
Will Smith . . . Jada Pinkett
John Tesh . . . Connie Sellecca
Donald Trump . . . Ivana Trump (Ivana Zelnicek)
Denzel Washington . . . Pauletta Pearson
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4 Years

Cary Grant . . . Virginia Cherrill
James Keach . . . Jane Seymour
Tiger Woods . . . Elin Nordegren
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5 Years

Dan Aykroyd . . . Donna Dixon
Prince Edward . . . Sophie Rhys-Jones
Prince Felipe (Spain) . . . Letizia Ortiz
Paul Newman . . . Joanne Woodward
Ray Romano . . . Anna Scarpulla
Ben Stiller . . . Christine Taylor
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6 Years

David Boreanaz . . . Jaime Bergman
Ted Danson . . . Mary Steenburgen
David Duchovny . . . Téa Leoni
Dodi Fayad . . . Princess Diana
Bob Hope . . . Dolores Reade
Lee Majors . . . Farrah Fawcett
Laurence Olivier . . . Vivien Leigh
Sean Penn . . . Robin Wright
Prince Rainier III . . . Grace Kelly
Steven Spielberg . . . Kate Capshaw
Roger Vadim . . . Brigitte Bardot
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7 Years

Richard Burton . . . Elizabeth Taylor
Clark Gable . . . Carole Lombard
Frank Sinatra . . . Ava Gardner
Spencer Tracy . . . Katharine Hepburn
Bruce Willis . . . Demi Moore
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8 Years

Russell Crowe . . . Danielle Spencer
Steve McQueen . . . Ali MacGraw
Nicolas Mirzayante . . . Princess Alexandra of Greece
Maury Povich . . . Connie Chung
Arnold Schwarzenegger . . . Maria Shriver
Kevin Sorbo . . . Sam Jenkins
John Travolta . . . Kelly Preston
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9 Years

Daniel Craig . . . Satsuki Mitchell
Johnny Depp . . . Vanessa Paradis
Bill Gates . . . Melinda Gates (Melinda French)
Christopher Reeve . . . Dana Reeve (Dana Morosini)
Roger Vadim . . . Jane Fonda
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10 Years

Bryan Brown . . . Rachel Ward
Jim Carrey . . . Jenny McCarthy
John Derek . . . Ursula Andress
Jonathon Frakes . . . Genie Francis
Christopher Guest . . . Jamie Lee Curtis
Elvis Presley . . . Priscilla Presley (Priscilla Beaulieu)
Ronald Reagan . . . Nancy Reagan (Nancy Davis)
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11 Years

Michael Bolton . . . Nicollette Sheridan
Richard Gere . . . Carey Lowel
Harry Hamlin . . . Lisa Rinna
Penn Jillette . . . Emily Zolten
Arthur Miller . . . Marilyn Monroe
Liam Neeson . . . Natasha Richardson
Brad Pitt . . . Angelina Jolie
Seal . . . Heidi Klum
Ringo Star . . . Barbara Bach
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12 Years

Mikhail Baryshnikov . . . Lisa Rinehart
Sonny Bono . . . Cher (Cherilyn La Piere)
Joe DiMaggio . . . Marilyn Monroe
John F. Kennedy . . . Jacqueline Bouvier
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13 Years

Jim Belushi . . . Jennifer Sloan
Pierce Brosnan . . . Keely Shaye Smith
Prince Charles . . . Diana Spencer
Gary Cooper . . . Sandra Shaw
Blake Edwards . . . Julie Andrews
Robert Graham . . . Anjelica Huston
Mick Jagger . . . Jerry Hall
David Letterman . . . Regina Lasko
Tom Selleck . . . Jillie Mack
Frank Sinatra . . . Barbara Marx
Rob Tapert . . . Lucy Lawless
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14 Years

Alan Barnette . . . Kim Delaney
Bjorn Borg . . . Patricia Ostfeldt
Bruce Boxleitner . . . Melissa Gilbert
Michael Caine . . . Shakira Baksh
Kelsey Grammer . . . Camille Donatacci
Loius Malle . . . Candice Bergen
Matthew McConaughey . . . Camila Alves
Mike Nichols . . . Diane Sawyer
Geraldo Rivera . . . C.C. Dyer
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15 Years

David Brenner . . . Tai Babilonia
Michael Flatley . . . Lisa Murphy
John Ritter . . . Amy Yasbeck
Jerry Soloman . . . Nancy Kerrigan
Roger Vadim . . . Catherine Deneuve
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16 Years

Richard Dean Anderson . . . Apryl Prose
Luc Besson . . . Milla Jovovich
Richard Brinkmann . . . Mena Suvari
David Carradine . . . Marina Benjamin
Tom Cruise . . . Katie Holmes
John Derek . . . Linda Evans
Kevin Kline . . . Pheobe Cates
Robert Lange . . . Shania Twain
Ric Ocasek . . . Paulina Porizkova
Bruce Willis . . . Karen McDougal
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17 Years

Dustin Hoffman . . . Lisa Gottsegan
Dennis Quaid . . . Kimberly Buffington
Charles Saatchi . . . Nigella Lawson
Jerry Seinfeld . . . Jennifer Crittenden
Jean Todt . . . Michelle Yeoh
Donald Trump . . . Marla Maples
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18 Years

Fabian Forte . . . Andrea Patrick
Don Johnson . . . Kelley Phleger
Paul McCartney . . . Nancy Shevell
John Mellencamp . . . Elaine Irwin
John O'Hurley . . . Lisa Mesloh
Gene Roddenberry . . . Majel Barrett
Patrick Stewart . . . Wendy Neuss
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19 Years

Cary Grant . . . Betsy Drake
Anthony Hopkins . . . Stella Arroyave
Steve Martin . . . Kristin Davis
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20 Years

Prince Albert of Monaco . . . Charlene Wittstock
Nicolas Cage . . . Alice Kim
John Rhys-Davies . . . Lisa Manning
Tony Curtis . . . Christine Kaufman
Les Moonves . . . Julie Chen
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21 Years

Warren Beatty . . . Annette Bening
Peter Brant . . . Stephanie Seymour
Lee Majors . . . Karen Velez
Robert Redford . . . Sibylle Szaggars
Jerry Seinfeld . . . Shoshanna Lonstein
Bruce Willis . . . Emma Heming
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22 Years

Phil Collins . . . Orianne Cevey
Kevin Costner . . . Christine Baumgarten
Peter Gabriel . . . Meabh Flynn
Edward M. Kennedy . . . Victoria Reggie
Wayne Newton . . . Kathleen McCrane
Laurence Olivier . . . Joan Plowright
Carlo Ponti . . . Sophia Loren
Alan Thicke . . . Gina Tolleson
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23 Years

Orson Bean . . . Alley Mills
Flavio Briatore . . . Heidi Klume
Harrison Ford . . . Calista Flockhart
John Forsythe . . . Nicole Carter
Frank Gifford . . . Kathie Lee Gifford (Kathie Lee Epstein) (same birthday: August 16)
Merle Haggard . . . Theresa Lane
Mick Jagger . . . L'Wren Scott
George Lazenby . . . Pam Shriver
Aristotle Onassis . . . Jacqueline Bouvier Kennedy
Sylvester Stallone . . . Jennifer Flavin
Steven Tyler . . . Erin Brady
Bruce Willis . . . Brooke Burns
Bruce Willis . . . Emily Sandberg
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24 Years

Hugh Hefner . . . Barbi Benton
Judd Hirsch . . . Bonni (wife)
Malcolm McDowell . . . Kelley Kuhr
Chuck Norris . . . Gena O'Kelley
Fred Thompson . . . Jeri Kehn
Donald Trump . . . Melania Knauss
Bruce Willis . . . Emma Heming
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25 Years

Humphrey Bogart . . . Lauren Bacall
Robert Conrad . . . LaVelda Fann
Michael Douglas . . . Catherine Zeta-Jones (same birthday: September 25)
Richard Harris . . . Ann Turkel
Benjamin Harrison . . . Mary Dimmick (He: 62, 23nd U.S. President [married after leaving office]. She: 37. Year: 1896.)
Christopher Knight . . . Adrianne Curry
Norman Lear . . . Lyn Davis
Paul McCartney . . . Heather Mills
Rod Stewart . . . Rachel Hunter
Mike Todd . . . Elizabeth Taylor
Bruce WIllis . . . Nadia Bjorlin
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26 Years

René Angélil . . . Celine Dion
Charles Dance . . . Shambhala Marthe
Mick Jagger . . . Luciana Morad
Larry King . . . Shawn Southwick
Steve Martin . . . Anne Stringfield
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27 Years

Jeff Goldblum . . . Catherine Wreford
Jerry Lee Lewis . . . Kerrie McCarver
Rich Little . . . Jeannette Markey
Rod Stewart . . . Penny Lancaster
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28 Years

Grover Cleveland . . . Frances Folsom (He: 49, 22nd U.S. President. She: 21, youngest First Lady. Year: 1886.)
Harrison Ford . . . Minnie Driver
Nelson Mandela . . . Graca Machel
Jack Nicholson . . . Sandra Knight
Kenny Rogers . . . Wanda Miller
William Shatner . . . Nerine Kidd
William Shatner . . . Elizabeth Martin
Alan Thicke . . . Tany Callau
Pete Townshend . . . Rachel Fuller
Bao Xishum . . . Xia Shusian (He: former world's tallest man 7'9")

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29 Years

George Hamilton . . . Kimberly Blackford
Yaphet Kotto . . . Tessie Sinahon
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30 Years

Paul Anka . . . Anna Yeager
Bing Crosby . . . Kathryn Grant
John Derek . . . Bo Derek (Mary Collins)
Frank Sinatra . . . Mia Farrow
John Tyler . . . Julia Gardiner (He: 54, 10th U.S. President. She: 24. Year: 1844.)
George Frederic Watts . . . Ellen Terry (He: 46, British artist. She: 16, actress. Year: 1864.)
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31 Years

Eric Clapton . . . Melia McEnery
Rodney Dangerfield . . . Joan Child
Robert Evans . . . Catherine Oxenberg
Dennis Hopper . . . Katherine LaNasa
Davy Jones . . . Jessica Pacheco
Martin Landau . . . Gretchen Becker
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32 Years

Billy Joel . . . Katie Lee
Ed McMahon . . . Pam Hurn
Geraldo Rivera . . . Erica Levy
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33 Years

Tony Bennett . . . Susan Crow
Cary Grant . . . Dyan Cannon
Jack Nicholson . . . Lara Flynn Boyle
George Frederic Watts . . . Mary Seton Fraser Tytler
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34 Years

Charles Dance . . . Sophia Myles
John McLaughlin . . . Cristine Vidal
Andre Previn . . . Anne-Sophie Mutter
Rod Steiger . . . Paula Ellis
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35 Years

Woody Allen . . . Soon-Yi Previn
Dennis Hopper . . . Victoria Duffy
Tony Robinson . . . Louise Hobbs
J.D. Salinger . . . Joyce Maynard (He: 53. She: 18. Year: 1972.)
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36 Years

Clint Eastwood . . . Dina Eastwood (Dina Ruiz)
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37 Years

Jim Clark . . . Kristy Hinze (He: 65, billionaire. She: 28, Australian supermodel. Married: 2009.)
James Doohan . . . Wende Braunberger
Hugh Hefner . . . Kimberley Conrad
Rupert Murdoch . . . Wendi Deng
Des O'Connor . . . Jodie Brooke Wilson
Patrick Stewart . . . Sunny Ozell
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39 Years

Robert Evans . . . Leslie Ann Woodward
Patrick Stewart . . . Lisa Dillon
James Woods . . . Ashley Madison (He: 57, actor. She: 18 when first met.)
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40 Years

Charles Bronson . . . Kim Weeks
Pablo Picasso . . . Françoise Gilot
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41 Years

Robert Duvall . . . Luciana Pedraza (He: actor. Both have same birthday: January 5)
Terry Jones . . . Anna Soderstrom (He: 62, "Monty Python" co-founder. She: 21 when first met.)
Ronnie Wood . . . Ekaterina Ivanova (He 61, "Rolling Stone" rock star. She 20, when first met.)
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42 Years

Leopold Stokowski . . . Gloria Vanderbilt
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44 Years

Fred Astaire . . . Robyn Smith
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45 Years

Tony Curtis . . . Jill Vanden Berg
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46 Years

Richard Roden . . . Lisa (wife) (He, Britain's oldest father of twins.)
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47 Years

Cary Grant . . . Barbara Harris
Anthony Quinn . . . Kathy Benvin
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48 Years

Kirk Kerkorian . . . Lisa Bonder
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51 Years

Tony Randall . . . Heather Harlan
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54 Years

Hugh Hefner . . . Holly Madison
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63 Years

J. Howard Marshall II . . . Anna Nicole Smith (He: 89. She: 26 when first met.)
Glynn Wolfe . . . Daisy (wife) (He: Guiness world record holder, world's most married man. She: young Asian bride.)
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95 Years

Ahmed Muhamed Dore . . . Safia Abdulleh (He: 112. She: 17 when married.)
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- End List -

Note: The names on this list are not intended to represent the current relationships of those listed, although in many instances that is the case. This is a list of past and present examples of dating and married couple celebrity relationships involving an older man-younger woman, near the same age, and same age that have been reported in various media over the years. The older person in the couple is listed first. The age difference numbers shown may vary by one year due to the fact that each person in the couple has a birthday during the year and his or her age changes. At some point and for a period of time during the year, however, the age difference shown exists.