This chapter reconstructs, in a descriptive and aspirational mode, lawful friendship through an encounter between the literary figure of ‘the friend’ and an international law of friendly and unfriendly relations. It begins with a gesture of elegiac friendship before locating friendship in an international law of enemies, criminals, pirates and neutrals. It finishes by elaborating a politics of international legal friendship and makes a plea for a tentative, careful friendliness suggested by friendships found in Montaigne, Nietzsche and Derrida, and in three moments of friendship set in the Cold War: one literary (the depiction of friendship in John Adams’ opera, Nixon in China), one an unlikely performance of anti-imperial friendly relations (the friendship between Nehru and Tito, begun in Belgrade) and one epistolary (a letter sent by Nikita Khrushchev to Fidel Castro in the aftermath of the Cuban Missile Crisis). Each represents in its rudimentary way a ‘lawful friendship’, a declaration on friendly relations.