The present article is a sequel of “Encounter with Death (I). An Interrupted Dialogue” (DOI:10.2478/rjp-2020-0013 Rom J Psychoanal 2020, 13(1):197-204) and it aims at exploring the possible psychoanalytical semantics of the double suicide committed by Arthur Koestler in 1983, together with his wife, Cynthia, at their home in London. It tries to relate the tragic event (in the context of Koestler's previous life-threatening experience in the prison of Seville) to the Freudian death drive and to Imre Hermann's clinging instinct, as approached in Philippe Van Haute and Tomas Geyskens's book “From Death Instinct to Attachment Theory”.