Wrote a simple app that emails people automatically asking them if they want to hangout. It reads my calendar and randomly decides whether or not we should hang out. The probability that it'll decide to ask gets higher and higher the longer we don't hangout, which it determines by reading my calendar.
Just an email. It was born from a project that died years back as one of my first YC submissions. Sounds like I need to resurrect it and add IM and SMS as a new MVP.