pretty [OE] In his diary entry for 11 May 1660, Samuel Pepys mentions ‘Dr Clerke, who I found to be a very pretty man and very knowing’. Pepys meant that the doctor was admirable, ‘a fine fellow’. This is merely one of the many senses that pretty, a word that comes from a root meaning ‘trick’, has had over the centuries. The first was ‘cunning, crafty’, which was followed by ‘clever, skilful’, ‘brave’, and ‘admirable, pleasing’ before the main modern sense, ‘attractive’ appeared in the 15th century, each step in itself easily followed, even if the modern sense has come a long way from the original. Around that time the meaning ‘considerable, great’ also developed, which is now only found in a pretty penny. Pretty has been used as an adverb in the sense ‘fairly, moderately’, since the mid 16th century. Sitting pretty, ‘comfortably placed or well situated’, is originally American, and is first recorded in 1915.