I was in bicoastal relationship for two years, but I don't think we would have used an app like this. It seems like just another place to have messages trapped (is there any way to export? why use this over text messaging or email?). IMHO, the benefit of this app versus the status quo has to be made clearer.

When you're starting out, go with free. I know your price points are very low, but the main friction is deciding what service to use to pay you through, deciding how much I trust that the billing will be honest, getting out my wallet, etc. When you want fast user growth, you need to be free.

The pricing is also confusing, because it isn't immediately clear that the annual pricing is for the same tier as the monthly. I'd swap the order of those two (keep the annual bigger) so that it's more logical for a left-to-right reader. First you introduce the tier (on the left) and then you introduce the annual upsell (in the middle). You could also try a variant of gotomeeting's pricing funnel, where they offer the discount in the second stage, after a user has selected a plan. This would simplify things further without really undermining your low-price message.