Mrs Warren's Profession, Candida, and You Never Can Tell are plays which give a clear sense of the range of Shaw's first forays into playwriting. Together they showcase his early negotiations between his political and social concerns and the constraints and possibilities of the British stage at the fin de siècle.

These plays are bound together by shared concerns with gender roles, sexuality, concepts of familial and social duty, and how all these are shaped by wider financial, political, literary, philosophical and theatrical influences.

Mrs Warren's Profession is the best known of Shaw's 'Plays Unpleasant', his first exercises in using the theatre as a means to awaken the consciences of morally complacent audiences. Written in 1893 in angry response to the success of A. W. Pinero's sensational hit The Second Mrs Tanqueray and a revival of Dumas's La dame aux camélias, Mrs Warren's Profession did not receive a public performance in Britain until 1925. Shaw's provocative response to the sentimental 'fallen woman' plays that dominated the fin-de-siècle stage was a play in which prostitution was presented not as a question of female sexual morality, but as a direct result of the systematic economic exploitation of women.

Candida (1894), by contrast, was categorised by Shaw as one of his 'Plays Pleasant', but the label was characteristically deceptive. The play appeared at first sight to offer audiences a reassuringly familiar drama of a marriage threatened by an interloper but ultimately reaffirmed when the wife recognises her true place and her dangerous admirer is sent out into the cold. But, as critics have noted, the play was a re-working by Shaw of Ibsen's A Doll's House in which the husband played the part of the over-protected doll, unaware of the real power dynamics of his marriage.

You Never Can Tell (1897) was Shaw's seaside comedy of manners, complete with an all-knowing waiter, exuberant twins, a lovelorn dentist, a long-lost father, lashings of food, and a comic catchphrase to provide the title. Shaw took all these familiar elements of Victorian farce and reworked them into a modern play of ideas, in which etiquette and ideologies collide. Just as in Wilde's The Importance of Being Earnest (a comparison which Shaw always stubbornly rejected), questions of class, marriage, manners, money, sex and identity underpin the plot of love-at-first-sight, mislaid parents and reunited families.