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  1. Sean Penn, Charlize Theron

    Sean Penn Is ''Surprised to Be in Love'' at 54 and if He Marries Charlize Theron He'd Consider It "a First Marriage''

    Wed., Jan. 28, 2015 6:31 PM PST
  2. Sean Penn

    Sean Penn: I Don't Miss My Gun Collection

    Tue., Jan. 13, 2015 1:30 PM PST
  3. Sean Penn, Charlize Theron

    Charlize Theron, Bill Clinton Help Sean Penn Raise $6 Million for Haiti

    Sun., Jan. 11, 2015 12:52 AM PST
  4. Sean Penn, Charlize Theron

    Charlize Theron and Sean Penn Are Talking Weddings: They're "Discussing When and Where"

    Mon., Dec. 29, 2014 3:13 PM PST
  5. Dylan Penn, L'Officiel Italia

    Dylan Penn Nabs Her First Major Magazine Cover with L'Officiel Italia—Check It Out!

    Mon., Dec. 29, 2014 3:05 PM PST
  6. Justin Bieber

    Justin Bieber Dyes Hair Platinum Blond, Sean Penn Goes Golden Too—See the Pics!

    Fri., Dec. 05, 2014 12:43 PM PST
  7. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn ''So Cute'' During Date Night in Hollywood: All the Details!

    Fri., Nov. 21, 2014 1:53 PM PST
  8. Sean Penn, Madonna

    Madonna's Wedding Dress From Sean Penn Marriage Sells for $81,250 at Charity Auction

    Mon., Nov. 10, 2014 6:13 AM PST
  9. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn Spotted Filming The Last Face Together in South Africa—See the Pic!

    Mon., Oct. 06, 2014 9:59 AM PDT
  10. Dylan Penn, Vanity Fair

    Dylan Penn Talks Robert Pattinson, Justin Timberlake and Her Naked Photo Spread

    Thu., Sep. 18, 2014 3:21 PM PDT
  11. Charlize Theron, Ring

    Is Charlize Theron Engaged to Sean Penn? Star Spotted With Gleaming Ring on That Finger

    Fri., Jul. 25, 2014 5:11 AM PDT
  12. Charlize Theron

    Charlize Theron Looks Incredible in Gold Dior Mini Dress With Sean Penn at Paris Haute Couture Fashion Week

    Mon., Jul. 07, 2014 10:08 AM PDT
  13. Charlize Theron Instagram

    Charlize Theron Sings With Seth MacFarlane During Date Night With Sean Penn—Get the Details!

    Tue., Jun. 03, 2014 1:17 PM PDT
  14. Charlize Theron

    Charlize Theron Wears Her Boyfriend's Giant, Black Undershirt and Still Looks Perfect—See the Pic!

    Wed., May. 28, 2014 3:00 PM PDT
  15. Charlize Theron, Sean Penn

    Charlize Theron Reveals What Might Happen If She Ever Breaks Up With Sean Penn—Watch Now!

    Tue., May. 20, 2014 10:46 AM PDT
  16. Charlize Theron, Vogue

    Charlize Theron Covers Vogue, Opens Up About "Effortless" Relationship With Sean Penn

    Mon., May. 19, 2014 9:13 AM PDT
  17. Jay Z, Beyonce

    Beyoncé and Jay-Z Release "Run" Music Video Featuring Blake Lively, Sean Penn and More: Watch!

    Sun., May. 18, 2014 8:30 AM PDT
  18. Kanye West, Kim Kardashian, MET Gala

    Kim and Kanye, Blake Lively and Ryan Reynolds, Johnny Depp and Amber Heard: See These Couples and More on the 2014 Met Gala Red Carpet

    Mon., May. 05, 2014 6:26 PM PDT
  19. Charlize Theron

    Charlize Theron and Sean Penn Enjoy Breakfast in Beverly Hills Together

    Wed., Apr. 30, 2014 7:21 PM PDT
  20. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn to Collaborate on New Film: 5 Other Star Couples Who've Joined Forces for the Big Screen

    Tue., Apr. 15, 2014 1:08 PM PDT
  21. Dylan Penn, Treats!

    Dylan Penn Naked! Sean Penn & Robin Wright's Daughter Strips Down for Magazine—See the Pics!

    Wed., Apr. 09, 2014 8:54 AM PDT
  22. Charlize Theron, Sean Penn

    Sean Penn and Charlize Theron Pack on the PDA in Malibu—See the Loved-Up Couple!

    Wed., Mar. 12, 2014 9:00 AM PDT
  23. Charlize Theron, Sean Penn

    Charlize Theron & Sean Penn's Dinner With Friends and Other Star Sightings

    Fri., Mar. 07, 2014 5:00 AM PST
  24. Dylan Penn

    Dylan Penn Naked? Playboy Offers Sean Penn and Robin Wright's Daughter Big Bucks to Strip Down

    Wed., Mar. 05, 2014 1:25 PM PST
  25. Madonna, Miley Cyrus

    Inside Madonna's Post-Oscars Party: Mila Kunis, Miley Cyrus, Brangelina and More

    Mon., Mar. 03, 2014 2:19 PM PST