The aim of this study is to investigate positional patterns of the preposition in the syntaxeme with “paired” pronouns, in particular, to consider possibilities and reasons for pattern usage of Russian prepositions with the pronoun друг друга. The study is based on extensive factual material obtained by continuous sampling from the Russian National Corpus. The frequency of antepositional, interpositional, and postpositional patterns of prepositions in syntaxemes at different time periods has been estimated.Along with the expected interpositional usage of non-derivative prepositions, instances of their antepositional usage and the reasons for their usage have been defined. An increase in such usage has been seen for the past 20 years.It has been found that the functioning of derived prepositions with the pronoun друг друга is determined, first of all, by the degree of their “assimilation” in the language. The interposition of derivative prepositions is similar to non-derivative ones and shows the weakening of bonds with the notional derivative word. The pronoun друг друга, as well as the forms of third-person personal pronouns, serve as a kind of marker while adapting new forms of prepositions in the language. Multi-component prepositions have the ability to be used interpositionally, but this is rarely the case.