Maxwell Sim can’t seem to make a single meaningful connection. His absent father was always more interested in poetry; he maintains an e-mail correspondence with his estranged wife, though under a false identity; his incomprehensible teenage daughter prefers her BlackBerry to his conversation; and his best friend since childhood is refusing to return his calls. He has 74 friends on Facebook, but nobody to talk to.

In an attempt to stir himself out of this horrible rut, Max quits his job as a customer liaison at the local department store and accepts a strange business proposition that falls in his lap by chance: he’s hired to drive a Prius full of toothbrushes to the remote Shetland Islands, part of a misguided promotional campaign for a dental-hygiene company intent on illustrating the slogan “We Reach Furthest.”

But Max’s trip doesn’t go as planned, as he’s unable to resist making a series of impromptu visits to important figures from his past who live en route. After a string of cruelly enlightening and intensely awkward misadventures, he finds himself falling in love with the soothing voice of his GPS system (“Emma”) and obsessively identifying with a sailor who perpetrated a notorious hoax and subsequently lost his mind. Eventually Max begins to wonder if perhaps it’s a severe lack of self-knowledge that’s hampering his ability to form actual relationships.

A humane satire and modern-day picaresque, The Terrible Privacy of Maxwell Sim is a gently comic and rollickingly entertaining novel about the paradoxical difficulties of making genuine attachments in a world of advanced communications technology and rampant social networking.