Heartbreak and failed romance form the bread and butter of fiction – practically always have done, and probably always will. Most people, unless they choose to spend their days under a rock or doing nothing but grinding on World of Warcraft, will eventually have their heartbroken by someone or other.

Simon Rich has taken this idea and run with it for thirty short stories about different aspects of love and, more specifically, the problems that arise from that word when things begin to go wrong. Like most anthologies, there are going to be some stories within that are better than others, and definitely there are some weak links in the chain here, but generally this is a very strong book from a great comic (Rich writes for Saturday Night Live). The stories are mostly told from a male point of view, and while some people may want to scream “Sexist!” at some of the ideas present, I think all of them, eventually, are supposed to show how ridiculous men are when it comes to their ideas of women. And, above everything else, the stories are all comedic and tongue-in-cheek.

I’ll pick out a couple of my favourite stories and discuss.

“Set Up” a great story about a chap in his thirties who, realising that all of his friends are getting married, asks them to set him up with someone which they delight in doing. Only, when it comes to meeting the girl, he discovers that she is a two foot six troll who usually lives under the Manhattan Bridge and doesn’t speak English. Concerned as he is, his friends apparently don’t understand the problem and become offended when he kicks her after she tries to bite his leg.

“The Adventure of the Spotted Tie” is about Holmes and Watson. While Holmes can tell with a glance that Watson has lost money at the dog track that day, he is completely unable to understand why a spotted tie would have appeared in the overnight bag of his girlfriend Alyssa. While Watson thinks it’s obvious, the great detective is stumped, theorising that someone must be trying to subvert the fabric tariff by smuggling clothes into the country.

“Wishes” has a woman come home to find her husband in talks with a genie, having used up forty-eight of his fifty wishes for sex, with the genie on hand to dole out some wise words about the nature of men.

“Unprotected” is, perhaps, the gem, and the first story in the collection. It is told from the point of view of a condom (yes, that’s right) who lives inside a wallet with his friends Learner Permit, Blockbuster Video, Visa and the dollars, who keep coming and going. It’s a brilliant creation, that character, who when told by MetroCard what his purpose in life is states, “I am too embarrassed to admit truth, which is that I thought I was a balloon.”

Alongside this fantastically naive condom, we also find Charles Darwin figuring out natural selection, a man getting maried to Mother Teresa, the Sex Aliens from Planet Sex, a hip-hop loving Cupid, modern day sirens, Santa Claus avoiding his “marriage of convenience” and, of course, the titular last girlfriend on Earth.

A great collection and worth a read for anyone who is or thinks they might be in love.