The construction analyzed in the article can be used both on the speaker’s initiative and in response to a request. It is characteristic of two speech genres, advice and compliment. The hypothetical substitution of ya (me) with ty (you) (ya by na tvoyom meste/if I were you) and ty (you) with ya (me) (ty by na moyom meste/ if you were me) can trigger conflict, to a greater or lesser extent. The relation between the action that provokes the utterance and the moment of speech, as well as the way in which speakers project their own behavior on addressees, may be the two variables determining the pragmatics of the construction. The study demonstrates that the construction ya by na tvoyom meste is more confrontational than its analog opening with the second-person pronoun (ty by na moyom meste) or with the possessive adjective “tvoy” (na tvoyom by meste ya). The speaker is entitled to a higher-rank control over the further development of the conversation and the interlocutor’s actions, claiming even those actions on the interlocutor’s part that are directed at third parties. Anteposition of the first-person pronoun (ya by na tvoyom meste) also demonstrates the speaker’s incapability of empathy. Postposition (na tvoyom by meste ya) may signal either knowledge of the addressee’s personality and the capacity for looking at things from the addressee’s perspective, or a claim to that knowledge and capacity. However, since the latter construction is less frequently used, both the actual and pretended knowledge and skill impose certain obligations.