For the cell phone txt messages, you can tell him there are some things you'd like to say but can't because they might be taken the wrong way by anyone who reads through his phone.

With the IM, low security is just to make sure his IM is set up not to save chat logs (same goes for yours). The Provider will probably have records of its own, so you still need to be judicious in what you say, but this prevents casual reading by others looking at his computer or phone. I wouldn't worry about a hug emoticon in that context.

If you're on the worrywart side you can easily set up private (encrypted) chat (see link below) and have him do it too with a few instructions. The encryption is not conspicuous as it's just a tick-box in the plugins menu of the pidgin.im multiple-messenger handler. The pidgin also allows you to run yahoo, msn, aim, and several other messengers together in the same window. Note that in encryption mode, it can't handle the traffic of transmitting photos or other files, so there can't be any suspicion that you're camming, transmitting naughty images or breaking copyright on artistic productions. It's only good for talking.

• ( http link ) Off-the-record messaging
[Anonymouse]