The big problem I see is that not only do you have to explain the whole concept to your potential senders, but also to the recipients. A major reason I see for

The big problem I see is that not only do you have to explain the whole concept to your potential senders, but also to the recipients. A major reason I see for why Google Wave failed is that it required all parties involved to have signed up (and while your service might not require the recipient to sign up, they still have to know what's going on...or maybe it doesn't? I'd like to see what explanation you'd give to the recipient along with the message or lack thereof). Actually, as I sit here overthinking things, I think your target audience is not people trying to avoid awkward social interactions, but people trying to avoid awkward social interactions because they overthink them, and what's to say they won't overthink past becoming a customer? If I send one of these things to my grandmother, I'm fairly certain she's going to not understand whatever explanation you provide in the email and try to ask me about it. Then, once I've explained that I tried to tell her something I don't want to say in person, we're already having a conversation about it, and I would have to say it directly to her, which is what I was trying to avoid. That's the kind of overthinking you don't want, because it takes away customers. Edit: having said that, I think it's a pretty neat idea and worth developing if you're still interested in it. Not sure I would pay money for something that could just as easily put me into the awkward situations I'd be trying to avoid.