We created Social Fortress[1] for this exact reason. Solve the root problem: Protect(AES256 Encrypt) and control your data transparently, prior to sending it anywhere, and you don't have to worry about this ever again.
Really neat idea, I like it. From watching the demo it would seem that anyone who I want to share with would also have to have SocialFortress installed as well?
Thanks. To see protected messages and photos, yes. You are able to toggle protection on and off in real-time so you can easily choose to send simple, less detailed, messages in plain-text and more detailed encrypted.
[1] I'm involved with https://www.socialfortress.com