The article presents a qualitative bilingual analysis of dialogues in Vladimir Nabokov’s novel Lolita, based on the original English version and the author’s own Russian version, in order to establish how the linguistic realization of the dialogues alters the characters’ dominant ego states and personality adaptations. The analytical framework integrates transactional analysis (Parent–Adult–Child ego states, transaction types, psychological games), the Joines and Stewart model of personality adaptations, and M.A.K. Halliday’s systemic functional linguistics (ideational, interpersonal, and textual metafunctions). The empirical base comprises 12 key dialogues between Humbert and Lolita, with each line presented in the English original and the author’s Russian translation. The Russian version systematically shifts the characters’ communicative positions: Humbert’s lines more often mark the Controlling Parent ego state, whereas Lolita’s mark an Adaptive Child with a high affective load; the English version is dominated by the neutral Adult with lower interpersonal modality. The linguistic markers of these shifts are discourse particles, repetitions, diminutive forms, and colloquial metaphors. Nabokov’s self-translation constitutes not a mere linguistic transfer but a deep psycholinguistic reinterpretation of the characters that intensifies conflict, power asymmetry, and emotional tension.