Jim is a thirty-three-year-old, emotionally stunted man who works at a miniature railway, and refuses to grow up. He lives in the granny flat at the back of his sister's house. Jim's pregnant sister Marie struggles with her oafish brute of a husband, Owen. Jim is unable to make a commitment to his English girlfriend of three years, Alice, who is very disappointed that Jim can't tell her that he loves her. Hoping to drive her boyfriend into saying those magical words, she considers taking a job in England, but to no avail. After a drunken night on the town with his mate Blake, Jim unsuccessfully attempts to steal a car, owned by the vertically challenged Charlie. Discovering an undelivered love letter Charlie wrote to Francesca, Jim cajoles Charlie into helping him mend his relationship with Alice. Jim's first attempt at a love letter fails as he is unable to express the words so he copies Charlie's original letter and gives it to Alice. Alice knows that the words aren't Jim's and is not impressed. Jim returns to Charlie's place and Charlie realises Jim copied his letter. Charlie tells Jim the words have to come from him so over a long afternoon and bottles of shiraz, Jim manages to write many rough drafts but he screws up all his work and gives up. Although Jim failed with Alice, he makes a commitment to Charlie to deliver his 3-year-old love letter. Charlie reveals that Francesca is supermodel Francesca Moretti with whom he is obsessed. Luckily Moretti is in town on a promotional tour and Jim takes Charlie to her book signing. Charlie gets cold feet and leaves but Jim hand-delivers the letter. Meanwhile, Charlie visits Alice and gives her a shoebox of Jim's writings, telling her, His handwriting's terrible, he writes like a doctor who lost both hands in the war. The words are coming; they're not quite there yet, but they're close. Later that evening Francesca reads Charlie's letter then invites him for a drink at her hotel. The two enjoy a pleasant evening together. Blake uses his influence to stall Alice's taxi ride to the airport to allow Jim to express his true feeling and to propose to her.
The film received mixed reviews. Review aggregator website Rotten Tomatoes reports that 54% of critics gave the film a positive review, based on 13 reviews, with an average score of 5.4/10.