I've had this happen quite a few times as well. I just had a conversation in iMessage this morning, and quite a long one. We were both using iPhones though. I noticed this odd thing happening too when I'd first send a message to someone with an IOS device, though it never happened with anyone on Mac OSX. Not sure why, but adding person in question to my contact list cleared it up, though I don't think that should be happening.
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I've had this happen quite a