This chapter examines the action of breach of promise of marriage to show its relationships with deception. It outlines how a broken promise of marriage, which could always imply deception regarding intention to keep the promise, attracted damages and highlights how known deception constituted an aggravation. The chapter also demonstrates how deception about certain features of oneself or one’s circumstances could justify a fiancé(e)’s decision to break a promise of marriage. Beyond these points, the chapter shows how conventions about relationships shaped the processes by which promises of marriage could be inferred or imputed, and it explores the links between actions of breach of promise of marriage and changing expectations of marriage, including the expectation that it should be based on real love. Through this process, the chapter offers an original argument about the decline of breach of promise at marriage which reveals its changing relationship to deception. The chapter concludes with some reflections on what actions of breach of promise suggest about the capacity of law to regulate promises and statements of future intention, as they relate to intimacy, in a contemporary context.