In the years between 1860 and 1868, Lewis Carroll wrote a number of poems about falling in love with a nameless woman; one or two describe allegories of sleeping with her and suffering agonies of guilt and pain as a consequence. At around the same time he was also confiding a sense of deep guilt and mental agony to his private diary, though he never admitted the cause of this pain. Coincidentally, or not, this is also close to the period that has been most heavily censored by his family. Two of the four missing volumes of his diary cover the years 1858-62.

His nephew and first biographer Stuart Collingwood acknowledged these poems were based on some deep personal 'disappointment' Carroll had experienced, but did not add any more detail, but despite this the potential meanings of this episode have for a long time been subsumed by the myth of Carroll's virginity and sexual indifference to adult women. Karoline Leach was the first to draw attention to it. She posited the possibility that Dodgson was engaged in a love affair with 'the real Alice's mother, Lorina Liddell. Other more recent suggestions for paramours have included Elizabeth Siddall (the wife of the painter Dante Gabriel Rossetti), and the actress Ellen Terry, though there is little evidence to link either of them with him romantically.