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 listen's 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.