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The achievement description says: 

Make 2 deals with the devil in one play through.

My only question is, does it count if I make two deals with the same appearance of the devil? When you meet the devil he always has two offers, if I take both, do they both count? Or does the achievement only count separate meetings with the devil?

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Yes, confirmed - you can unlock Eve by making two deals with the same devil (i.e. purchasing both deals in the one room). By side effect, you also unlock her Dead Bird and Whore of Babylon ("The Curse"), which is announced upon leaving the room.

Source: Me, having just now done exactly that and unlocking her.

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  • I had tried it and it hadn't worked. But I guess they changed it in this update that happened just 30 min ago. =)
    – Malabarba
    Nov 2, 2011 at 3:32
  • I made two deals with the devil today and didn't get the achievement/unlock. I read on the wiki somewhere you need to make three deals in one play. Any truth to this?
    – Dycker
    Nov 2, 2011 at 4:57
  • @Dycker Every official source including the game itself (in character select) says two deals.
    – doppelgreener
    Nov 2, 2011 at 5:47
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    @Dycker There was a bug, which required you to make three deals with him. This should be fixed in the latest patch.
    – mordi2k
    Nov 2, 2011 at 6:42
  • I tested after update, and @JonathanHobbs is right.
    – Malabarba
    Nov 2, 2011 at 13:27
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If the patch notes are to be believed, then you have to make a total of 2 deals with the devil in two separate encounters.

Source: http://store.steampowered.com/news/6676/

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