The paper discusses the character system of “The Seagull” in terms of “human fullness”. Chekhov’s concepts of “living life” and “living people” are regarded as the author’s response to the socio-moral typification principle and “mise-en-scene sensation” of contemporary theater. Medical knowledge and artistic intuition allowed creating plot situations with social characteristics playing a secondary role. Subconscious factors come to the fore, becoming decisive in the structure of an individual and his relations with others. The hidden motives of the relationship between mother and son (Arkadina – Treplev), lovers (Arkadina – Trigorin, Polina Andreevna – Dorn), wife and husband (Medvedenko – Masha), common-law wife and common-law husband (Nina – Trigorin) are analyzed. One of Treplev’s character traits is nervousness. Most remarks concerning his image reveal his emotional state, a classic neurotic. “The Oedipus complex” can be seen not only in the Treplev-Arkadina storyline. As Freud claims, Nina Zarechnaya needs a father as a man model, a protector and A helper. However, she considers him a “traitor,” for he married another woman after her mother’s death. Thus, in psychology of love, she transfers her unsatisfied love for her father (Philia love) into love for Trigorin (Eros Love). In terms of gender psychology, Trigorin belongs to a certain psychotype preferring to marry women of older age for they require a mother-wife to dominate and solve their problems. Polina Andreevna’s husband mostly conforms to gender stereotypes, dominating the family, being sometimes aggressive towards other people, rude in relationships with women. Dorn is often seen as Don Juan, but this is a different psychotype – a bachelor. Don-Juan has no affection and will not interact with a woman seduced twenty years ago. A snuffbox, wine, black dresses are Masha’s challenge to the world when playing the role of a “bad girl” to draw attention to herself. In terms of psychoanalysis, her personality is dominated by the Child, with no strength or desire to become an Adult. To sum up, “living life”, children and parents in the aspect of psychoanalysis, male and female in the characters make “The Seagull” always modern.