There's nothing wrong with the sideways-glance approach to the philosophical canon. Andrew Shaffer's Great Philosophers Who Failed at Love is a slim, friendly book that asks a pertinent question: if folks like Saint Thomas Aquinas, Simone de Beauvoir, John Calvin, David Hume, Immanuel Kant, Jean-Jacques Rousseau and Emanuel Swedenborg were so smart, how did they manage to meet life's most personal challenge? Were they able to find true love, and if so were they able to sustain happy long-term relationships? What can we learn from the choices or mistakes they made?

The book offers gossipy stories about thirty-seven philosophers, some with clear parallels to their subjects' ideals. The original existentialist Soren Kierkegaard was famously indecisive about whether or not to marry a conventional young woman named Regine Olsen, and wrote a book called Either/Or to describe the agony he felt in this position. Arthur Schopenhauer was gloomy about the possibilities of romantic love, and validated his gloominess by living and dying alone. Jean-Paul Sartre believed in ultimate human freedom, and his open relationship with Simone de Beauvoir reflected this belief (in Sartre's rare case, it's hard to see how the book's title fits -- this is one philosopher who does not seem to have failed in love).

Other philosophers seem to have carried out their love lives with less intellectual consistency. The socially incisive Immanuel Kant might appear to have been good marriage material, but seems to have had absolutely no romantic history at all. Jean-Jacques Rousseau refused to establish a "social contract" with any of the five children he fathered with his lover, insisting that she give them all up for adoption. The allegedly ultra-rational Ayn Rand became deeply irrational after her much younger lover Nathaniel Branden fell in love with another woman. Georg Wilhelm Friedrich Hegel considered women stupid, and his messy personal entanglements fell far short of the transcendental Hegelian ideal.

This book feels like a quickie takeoff on Simon Critchley's more thoroughly researched Book of Dead Philosophers (which is cited in the bibliography), and it suffers from the same major flaw: a tendency to turn great philosophers into cartoons, and to reach for the punchline instead of the substantial insight.

Andrew Shaffer is a professional literary prankster; he runs a couple of funny twitter accounts and managed to get his atheist Christmas Cards on the Stephen Colbert show. His busy schedule may not have included enough library hours, though, because some of the mini-biographies show superficial research. Henry David Thoreau did not "live a simple life in the woods", though he did go to the woods often. It's technically correct that Fyodor Dostoevsky was in a Siberian army regiment when he met his first wife in 1856, but Shaffer doesn't seem aware that Dostoevsky was serving out a brutal prison sentence at the time. The short section on Plato is terrible and completely misleading; Shaffer has clearly not read my blog post entitled "Everybody Please Stop Giving Plato Shit About Music and Poetry" and would have written a much better chapter if he had.

Still, Shaffer's literary and philosophical instincts are commendable even if his research is occasionally shaky, and the list of philosophers included in this book -- Engels? Swedenborg? Henry Ward Beecher? cool! -- shows evidence of a broad, inclusive mind. The author's background in greeting cards ultimately works in this little book's favor. Great Philosophers Who Failed at Love will not win any genius grants or blow your mind, but it would make a nice thoughtful gift for someone you love.