Still grieving the loss of his wife, Craig doesn't think romance is right for him - at least not yet. But that starts to change when he locks eyes with a woman on the bus. Unnerved, excited, and far more interested than he feels he has a right to, Craig listens to the advice of a good work friend and chooses to try to shake his depression by responding to a Craigslist Missed Connections ad.
In a fateful turn, that ad leads a roundabout route directly to the woman on the bus. That moment, and a few more strange Craigslist Ads, leads to a journey of adventure, flirtation, and a revelation that just may destroy whatever fragile happiness Craig has started to build.