С ней он мог говорить о литературе,

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

Результаты (английский) 1:

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

Результаты (английский) 2:

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

Результаты (английский) 3:

with her he could talk about literature, about art, about anything, can complain to her life, to people