"How Were We To Know" è intrisa di drammaticità e spettacolo: Emeli padroneggia l'arte della costruzione lenta aprendosi con un devastante grido in falsetto, avvolto da dolci tastiere e da archi. Anche se all'inizio sembra fragile, la sua voce si fa sempre più risoluta mentre assolve se stessa e la persona amata da ogni colpa per la fine della loro relazione. Al culmine della traccia Emeli libera tutta la forza della sua voce, lasciandola volare in alto, cantando con un'emozione che non ha filtri. La canzone è un trionfo e ci mostra una Emeli all'apice delle sue doti vocali.

Emeli ha affermato: “I wrote 'How Were We To Know' at a time in my life where I was reconciling with myself after the end of a relationship that left me undone and re-evaluating my view on love and life. I was highly emotionally charged the day I wrote, and recorded it with Chris Loco and Phil Leigh and the lyrics and melody seemed to flow out effortlessly as the chords began to play. 
There will always be a period of anger, disappointment and blame at the end of a relationship but carrying those emotions can make life so much heavier than it needs to be. To fall in love takes bravery, vulnerability and completely letting go of logic.
To me, love is a return to innocence which can often leave you naïve to the realities of life. Although the end can be brutal and leave you devastated, it’s unfair to punish yourself for giving your all and trusting in love. I see this song as a plea for understanding and compassion for yourself and former relationships. In both life and love there is no way of knowing the ultimate outcome of any situation.”.