In the ten years between 1858 and 1868, Lewis Carroll wrote a number of seemingly very personal love 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. His nephew and first biographer Stuart Collingwood admitted these poems were based on some deep personal sadness Carroll had experienced. At around the same time that he was writing these poems Carroll 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 the period that has been most heavily censored by his family. All but one page of the material now missing from Dodgson's diaries belongs to the troubled decade 1858-1868.

The obvious conclusion that Dodgson was very likely involved in some traumatic and guilty love affair at this time has been subsumed by the myth of his virginity and sexual indifference to adult women, and the meaning of this episode therefore remained entirely unexplored. Karoline Leach was the first to draw attention to it in her book In the Shadow of the Dreamchild. She posited the possibility that Dodgson was engaged in a love affair with 'the real Alice's mother, Lorina Liddell, and drew together some circumstantial evidence that offered support for this.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.