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Booking Awkwardness

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?

Reader Interactions

Comments

  7. Pierre Latin says

    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.

  10. Jester says

    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.

  11. dontpanik says

    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

  18. DrunkyMcPuncherson says

    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

  21. Buzz Spill says

    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.

  22. Becky S says

    How about serial cheater Ben Affleck and Blake Lively.

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

  23. wfreshie says

    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

  24. Charlie28 says

    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.

  26. Pierre Latin says

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

  27. Pierre Latin says

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

  28. shelaur22 says

    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.

  29. maximusmom11 says

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

  30. rhiannon14 says

    “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.

  31. keeley123 says

    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”.

  32. flushingdrycement says

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

  33. JennyJustice says

    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.

  34. bhakti says

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

  38. WaitLemmeGuess says

    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.