PHILIP HENSLOWE was the fourth of seven children of Edmond and Margaret Henslowe (or Hensley) of Lindfield, Sussex. We do not know when he was born, but it is likely to have been between 1550–60, which would have made him about sixty when he died. He appears to have acquired little of either education or patrimony, and to have begun his career as an apprentice or servant to a London dyer by the name of Henry Woodward. Philip's diligence in the execution of his duties must have recommended him (at least to his mistress), for on 14 February 1579 (a mere two months after her husband's death), Agnes Woodward and Philip Henslowe were married. At a stroke, the former servant acquired not only a readymade family (6-year-old Joan and 4-year-old Elizabeth), but also a substantial estate.

Henslowe was probably in his mid- or late twenties at the time of his marriage; his new wife was considerably older. No record of Agnes’ birth date survives and the only clue we have to her age is a deposition made after Henslowe's death in 1616 alleging that she was then a hundred years old. This testimony by Philip's nephew is almost totally untrustworthy, however, since it would make Agnes fifty-nine years old at the time her second daughter was born (and sixty-three when she married Philip). It is more likely that she was in her early fifties in 1579.