Roddy Doyle is one of the most prominent Irish literary figures of our time. The vicissitudes of Irish middle class families, domestic violence, prominent events in Irish history and Ireland’s new multiculturalism are some of the leading themes that he employs in his works. His short story collection Bullfighting (2011) is unique in dealing with a subject matter unfamiliar in his other works: the midlife crises of working-class men. Specifically, the short stories “Recuperation”, “Teaching”, and “Bullfighting” revolve around middle aged men who have no expectations in life and are entrapped in vicious familial, matrimonial or socio-cultural circles. In a similar way to the aforementioned short stories, Doyle’s novel Two Pints (2012) recounts the pub meetings of two Irish men in late middle age. A reflection of each other, these men chat about various subjects such as politics, economy, and dead celebrities, forging bonds as they drink pints together. It could be possible to claim that these two men offer a counterpoint to the male characters found in Bullfighting. They have given up questioning their lives, accepting the facts of life as they are. Bearing all this in mind, this paper aims to analyse the following points: 1) if we compare Bullfighting and his most recent work, Doyle’s characters seem to have become older and less pessimistic; 2) the motifs of the pint and the pub meeting function as therapy for his male characters; 3) the tones of both works differ: the bleak tone of the short stories has given way to a humorous tone in the novel. In short, with its aged male characters, Two Pints represents a more light-hearted, humorous version of certain stories in Bullfighting.