> Is there a way to be able to have off-the-record email conversations
> with GPG technology? It would definitely be a terrific thing.

Not really.  OTR uses DHKEA for symmetric key negotiation.  This is an 
interactive protocol: you send some information, the other person sends some 
information back, back-and-forth a few times until a symmetric key emerges from 
the mathemagic.

Email is not an interactive protocol.  You could probably invent a way to do 
OTR via email, but it would probably be a horrible kludge.

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