Patriotic war culture has routinely touted the symbiosis between mail and morale. Disciplinarians of wartime feeling have issued reams of advice about how to “write right!” in order to sustain men’s esprit and keep love alive despite distance and danger. Above all, military and civilian opinion-leaders alike have strenuously and repeatedly warned women against dispatching Dear Johns to men serving overseas. These prompts have taken many forms: explicit guidance from newspaper and magazine columnists, marriage counselors, government bodies, and voluntary agencies (like the YMCA and Red Cross) as well as pointed cues about emotional etiquette supplied by popular music, radio and television shows, and Hollywood movies. This chapter probes the challenges of sustaining long-distance love at war – difficulties often minimized by wartime advice-givers, but unmistakable to men and women who have tried, and sometimes failed, to keep intimate relationships intact. It also considers how far prescriptions issued to “waiting women” have changed since the 1940s, proposing that there’s been considerable continuity, despite radical shifts in dating behavior and marital norms in US society.