С ней он мог говорить о литературе,

С ней он мог говорить о литературе, об искусстве, о чем угодно, мог жаловаться ей на жизнь, на людей

Результаты (английский) 1:

He could speak with her about literature, about art, about anything to complain about her life, people

Результаты (английский) 2:

With it, he could talk about literature, about art, about anything could complain to her life, people

Результаты (английский) 3:

With it he could speak on the literature, the arts, and the than anywhere, could complain about it on the life, the people