The compositional development of 'The Long Engagement' is a long story, revealing much about the hesitant and scrupulous nature of its artist. On a visit to Rossetti's studio on 13 March 1854, G.P. Boyce noted, 'A young man of the name of Hughes was painting a picture of Orlando inscribing his mistress' name on a tree. Parts nicely painted.'

Having apparently reversed the composition (with the tree on the left), in August 1854 Hughes painted a detailed background of wild roses in the open air.

Dissatisfied with the figure of Orlando and with the Shakespearian subject, Hughes wiped it out and at a later date began to devise a two-figure composition of 'modern lovers'. The three sketches on this sheet show Hughes trying to work out the composition of the two figures.