Set in a Scottish New Town, the story revolves around Gregory (John Gordon Sinclair). Gregory and his mates are just beginning to discover girls. He has his eyes on Dorothy (Dee Hepburn).Dorothy is a young footballing talent. Clearly a better football player than him, who has taken her place in the first eleven.
Gregory tries to win the affections of Dorothy and eventually finally plucks up courage to ask her out, but soon finds this relationship a lot more trouble than he expected. Unsure where to turn for advice, he finds his mates are no help and so turns to his younger sister, who seems a lot more clued up on matters of romance even though she is much younger and much more interested in ice cream.
Dorothy eventually spurns Gregory's advances and passes him on, instead, to Susan (Clare Grogan).
This is a charming quirky tale, full of plenty of absurd and downright funny moments. All the teen characters are interesting and the dialogue is sharp. The performances are all great, but Sinclair, in particular, does a great job at pulling off the likeable gangly youth Gregory.
Director and star were reunited for a sequel in 1991 Gregory's Two Girls.
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