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Booking Awkwardness

May 20, 2016 Blind Gossip

couple date 5[Blind Gossip] This actor and actress had a fling a few years ago. It went hot and heavy while they were together… but ended with a screaming match and an icy freeze out. As far as we know, the two now make sure to stay far away from each other.

Well, we found out that the two have just booked the same project! What? Did they know the other person was on board before they signed up for this, or did they accept the role and then find out? Will there be a sudden recasting when they both realize what’s going on?

Whatever the case, we’ll be keeping a close on these two as filming starts!

Similar: Competitive Dating

Actor:

Actress:

[Optional] Have you ever had to work with someone with whom you had broken up? How awkward was it?

Blind Items actor, actress, dating

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Reader Interactions

Comments

  1. WaitLemmeGuess says

    May 25, 2016 at 12:45 pm

    You might be thinking of Olivia Wilde? He dated JJ very briefly right before JJ got pregnant with her kid. Some speculate he’s the dad but I think it’s some married executive.

  2. valleygirl86 says

    May 24, 2016 at 11:21 am

    jason’s married and going on his second baby with olivia wilde…

  3. huhwhoami says

    May 23, 2016 at 4:01 pm

    Oh pay; me 3 million? I will put up. I am an actor/ess.

  4. bhakti says

    May 23, 2016 at 12:36 pm

    Did they break up? ?

  5. bhakti says

    May 23, 2016 at 12:35 pm

    Excellent clue detection. I didn’t pick up on any of that. I think you’ve nailed this blind.

  6. JennyJustice says

    May 23, 2016 at 8:29 am

    I like this guess and the clues you found.

    If it is them, Goop would be more than happy about it for the tabloid fodder, hoping he’d still have the hots for her, and generally sh!tting on Jennifer Garner….just because.

  7. flushingdrycement says

    May 22, 2016 at 8:12 pm

    a suggestion, Christian Bale and Anne Hathaway – they were rumored to have a “hot fling” while filming The Dark Knight Returns

  8. keeley123 says

    May 21, 2016 at 8:45 pm

    Agree. They’re in a restaurant which may be a clue to Gwyneth’s cookbook and food obsession. The two of them were in a movie together about a plane crash and the clue says “booked the same project” and “was on board”.

  9. rhiannon14 says

    May 21, 2016 at 7:54 pm

    “Had a fling a few years ago”…Sean Penn & Charlize Theron broke up less than a year ago. Not them.

    The woman in that photo totally has Goopy hair.

    I’m going with Paltrow/Affleck…supposedly he cheated on her…as he has with every serious relationship. She once said that Affleck would be better off dating a Scores stripper.

  10. maximusmom11 says

    May 21, 2016 at 6:55 pm

    Kirsten Dunst and Jake Gyllenhaal? Clues being match(Wimbeldon) freeze out(Day after Tomorrow).

  11. shelaur22 says

    May 21, 2016 at 6:35 pm

    The blind makes it sound like they don’t know that the other was cast yet. Ben would know if she was, since he is directing that project. I don’t think this is them.

  12. Pierre Latin says

    May 21, 2016 at 2:21 pm

    It could be Gwyneth Paltrow with Robert Downey Jr. or his ex-boyfriend Ben Affleck.

  13. Pierre Latin says

    May 21, 2016 at 2:19 pm

    This. I heard Blake Lively is going to be in the new Batman Ben Affleck movie.

  14. Pierre Latin says

    May 21, 2016 at 2:17 pm

    This

  15. Charlie28 says

    May 21, 2016 at 1:10 pm

    If it was several years ago they probably are over it and don’t care. I don’t think it’s Charlize and Sean because they didn’t have a fling. They had a serious relationship.

  16. wfreshie says

    May 21, 2016 at 11:17 am

    this sounds like something that is filming now or will be filming..I don’y see anything that charlize is filming that has sean penn listed as well…must be some other pair

  17. Becky S says

    May 21, 2016 at 8:08 am

    How about serial cheater Ben Affleck and Blake Lively.

    Yes, and it is awkward. That’s why workplace affairs are not a great idea.

  18. Buzz Spill says

    May 21, 2016 at 1:30 am

    Actor: Sean Penn

    Actress: Charlize Theron

    [Optional] Have you ever had to work with someone with whom you had broken up? How awkward was it?
    It was fine. I’m on good terms with all of my exes and we were professional adults who put their best foot forward while working together. It may help that I am a decent person who only dated good, worthwhile people.

  19. fotosbysal says

    May 21, 2016 at 1:13 am

    Guy Pearce
    Kylie?

  20. Sharcat says

    May 21, 2016 at 12:08 am

    Actor: Sean Penn

    Actress: Charlize Theron

  21. DrunkyMcPuncherson says

    May 20, 2016 at 11:59 pm

    I’m thinking this could be anyone in Hollywood.

    Never worked with an ex, but did work with who was then a current boyfriend, on a big deal big $$ project, and he kept calling me ‘baby’ in front of my client after I repeatedly asked him not to, so yeah, that was awkward. Needless to say he is an ‘ex’ boyfriend now. :-p

  22. CaliBeat210 says

    May 20, 2016 at 10:08 pm

    charlize theron and sean penn

  23. pinaydiva says

    May 20, 2016 at 8:49 pm

    Sean Penn
    Charlize Theron

  24. bostonbratt says

    May 20, 2016 at 8:19 pm

    Reese Witherspoon and Jake G

  25. WaitLemmeGuess says

    May 20, 2016 at 7:31 pm

    January Jones and Jason Sudeikis?

  26. thisisannoying says

    May 20, 2016 at 7:23 pm

    Liam Hemsworth and January Jones?

  27. kimgee76 says

    May 20, 2016 at 6:36 pm

    Actor: Sean Penn

    Actress: Charlize Theron

  28. dontpanik says

    May 20, 2016 at 5:47 pm

    Actor: Ben Affleck
    Actress: Goopy Paltrow

    [Optional] Have you ever had to work with someone with whom you had broken up? How awkward was it? um…Nope

  29. Jester says

    May 20, 2016 at 5:20 pm

    Sean Penn and Charlize Theron – both at Cannes, but keeping a distance.

    Happily no. I have not had to go through this because I never dated anybody that I worked with in my career.

  30. monorail says

    May 20, 2016 at 5:09 pm

    or could it be Luke Wilson and Kate Hudson

  31. monorail says

    May 20, 2016 at 5:06 pm

    Sean Penn and Charlize Theron

  32. Pierre Latin says

    May 20, 2016 at 5:03 pm

    Actor: Casey Affleck or Ben Affleck.

    Actress: Kate Hudson or Gwyneth Paltrow.

    Optional: Bad. I was OK but my ex tried to had rebound sex with me. I was with other person already so I rejected her once again. She was extra furious.

  33. kermit1969 says

    May 20, 2016 at 4:45 pm

    Actor. Ben Affleck

    Actress: gwyneth paltrow

  34. Goodgrief says

    May 20, 2016 at 4:33 pm

    Then again maybe not.

  35. Goodgrief says

    May 20, 2016 at 4:32 pm

    This screams Charlize Theron and Sean Penn in Cannes.

  36. spunkie brewster says

    May 20, 2016 at 4:29 pm

    Sean Penn
    Charlie Theron

  37. Once In A While says

    May 20, 2016 at 4:26 pm

    Kate Hudson and Owen Wilson?

  38. goggles says

    May 20, 2016 at 4:24 pm

    Charlize Theron

    Sean Penn

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