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Born into relative wealth, Scott Moncrieff had an enjoyable childhood – his Father a Scottish Sheriff, his mother a warm, creative and intelligent figure. Moncrieff was clearly an incredibly intelligent child – letters show that he was self-aware, charming, and hugely well read. Boarding school proved a relatively enjoyable experience for the young Moncrieff, and his poems show that, even from a very young age, he was a talented individual. Whilst on a scholarship at Winchester College there were struggles to reconcile his homosexual feelings with his fairly religious upbringing and Moncrieff also fell head over heels with countless fellow schoolboys, prompting him to publish a story (with mentions of homosexual love) in the school magazine, resulting in him ruining his chances for further education at Cambridge or Oxford.