Sentimentality commonly figures as always already too much in twentieth- and twenty-first century discourse — from literary criticism to pop musical commentary. The Merriam-Webster Dictionary, for instance, offers the following as one possible definition of sentimentality: “[H]aving an excess of sentiment or sensibility” (Merriam-Webster n.d.). But which sentiments are included here and why are they considered excessive? Who has “gone too far” and in what ways? In this article, I listen across the long history of English-language sentimental songs in order to show that while sentimentality has persisted, ideas about emotional excess have shifted over the last two hundred and fifty years particularly with regard to love and masculinity. This broader history reveals that — unsurprisingly — sentimental men were present from the beginning, engaging song as a space for opening up in loving ways. In so doing, my aim is not to reinscribe binary gender stereotypes, but rather to untether the longstanding and still prevalent associations between femininity and excess emotional expression.