Jenny is a 40 something, adventure-seeking mum, forced to move back in with her parents in a posh suburb of Glasgow, after her marriage broke down (in no small part due to her lust for life...and the gardener!).
Bored of her life back in this middle-class enclave, and in a search of some excitement, she's registered with a website called Jailmates.com and begun corresponding with inmate Gerry, a fellow Glaswegian from the other side of town, currently serving 18 months for stealing books and selling them online.
Their backgrounds and experiences of life couldn't be more different - on a day-to-day basis, Jenny worries about not fitting in with the other mums at the school gate, while Gerry's just trying to make it through the day unscathed.
Jenny is frustrated by the expectations placed upon her by the world, constantly rejecting pressure to conform, and - albeit in starkly different circumstances - Gerry is too.
Through this series of hilarious letters, they discover a common ground and compatibility, but will a relationship develop?