After a failed attempt at an acting career, Mary married the second son of the Earl of Cholmondeley and chose to live as a socialite.

With connections in both English and French high society, she came to have a "modest salon", and was close friends with Frances Burney and Samuel Johnson.

Little is known about Mary's youth but it is likely she had minor roles in her sister's productions, including nearly 100 performances of The Beggar's Opera at New Booth Theatre, Dublin.

[3] In mid 1744, aged 15, Woffington returned to England and moved into her sister's country house at Teddington, where she began courting members of the local gentry.

Peg, with the help of David Garrick, Richard Brinsley Sheridan, George Anne Bellamy and others, aided Mary by staging a practice performance of The Distrest Mother at Teddington.

Mary's professional debut occurred on 30 March 1745, when she performed the role of the maidservant Cherry in The Beaux' Stratagem at Drury Lane Theatre.

In a letter to the Duke of Newcastle, the already-impoverished Earl Cholmondeley wrote the marriage had alarmed his creditors, forcing him to sell much of his remaining property.

[4][8] Woffington was popular in London drawing rooms for her "engaging personality and quick intelligence", as well as her connections in theatrical and intellectual circles, and she came to have a "modest salon".

[9] Woffington was a frequent subject of Walpole's letters; he squired her in France and introduced her to Madame du Deffand, who in turn sponsored her in Parisian high society.

After spending a year in France, Woffington became disinterested in high society, preferring to be "in the company of artists, actors, and literary folk".

Byrne-Costigan states nine of the ten "made splendid marriages",[5] while according to Philip H. Highfill and John Doran, only four and five, respectively, survived past infancy.