The idea to write this article was inspired by a Ugandan-born English writer, Anthony Capella, who is the author of the novel The Various Flavours of Coffee (2008), in which coffee flavours are compared with the varying ‘flavours’ of love depending on the protagonist’s many flirts. I will argue that coffee traditionally accompanies emotional experiences to fight against stress and moodiness or it can be seen as a shelter or a facilitator of relationships. As widely acknowledged, coffee is some sort of ritual enjoyed, first in the morning for a caffeine boost to power your day, during coffee breaks, and after meals. We will see how such functions represent the role coffee had throughout history. Initially, coffee houses grew as meeting places for discussing business and matters of high historic and social relevance. Then, they acquired a key role in the literature world, and became literary cafés. Thus, it is not incidental that poems, short stories, music compositions, and even novels have been dedicated to coffee and cafés have been used as the ideal place where stories were set. Besides referring to some leading world writers and artists, I will focus on some of the most prominent Italian examples, including Goldoni’s La bottega del caffè (1750), Luigi Pirandello’s L’ultimo caffè (1912), and among contemporary writers to Luciano De Crescenzo with Il caffè sospeso (2017). You can bump into a ‘caffé letterario’ even in the remotest areas of the country. Keywords: coffee, coffee house, literary café, literature, relationship, flavour, culture, energiser