This would work easiest for something like emailing, but could also be used for IM chat.
The 'coach' could even listen in on a phone conversation (without her knowing and give live phone conversation advice via IM (while I'm on the phone).
And on dates, the "coach" could spy on the date and speak to me via an earpiece (like they do on tv shows with agents undergoing secret operations and stuff like that)
Granted that sounds a little creepy but still, it'd be effective. and then once she started liking me, i wouldnt need a coach anymore cuz she'd be attached.
read my above post