Like his father and grandfather before him, Calcraft seems to have formed an unfortunate passion for the theatre. While at Oxford, John Stuart Wortley* reported to Henry Fox*, 5 June 1821, that ‘little Calcraft has been great fun lately. There has been a strolling company at Witney of which he made himself manager and one morning went over by himself and had a theatrical fund dinner’.
It was on his return in 1828 that he became smitten with the actress Emma Love, as she was known, perhaps for her role as Lilla in Cobb’s comic opera The Siege of Belgrade at the Drury Lane Theatre. In November 1828, at St. Pancras church, he contracted a marriage with her, which was kept secret from his father, who he thought would disapprove, and (for a time) from her mother and companion Mrs. Love, who loathed him. He soon wished to overturn this arrangement, by which she continued to live with her mother while they each pursued their careers, especially as she started to receive visits from the 6th earl of Harborough, a former admirer. Calcraft quarrelled with him on one occasion, and she declared that ‘she would rather sweep the corners of the streets than be his mistress, if that was his object’. But in July 1829, when Calcraft was at his barracks in Gosport, Harborough enticed ‘Miss Love’ away from her lodgings in Nottingham, where she was playing, and installed her in a cottage near his house at Stapleford Park, Leicestershire.
Calcraft, who canvassed on behalf of his father in the contest for Dorset and helped lead a party of his pro-reform supporters to the hustings in Dorchester, was elected in his place for the family seat of Wareham at the general election of 1831.
Thereafter he resided at a series of addresses in London and elsewhere, and he may have been the Calcraft who, as lessee of the Theatre Royal, Dublin, brought an action against a rival establishment in January 1836. He became insolvent in 1839, but successfully petitioned for release from the Fleet prison late that year.
