An English traveller, Josselyn, gives a glimpse of Boston love-making in the year 1663.

This simple and quaint picture of youthful love in the soft summer twilight, at that ever beautiful trysting-place, gives an unwonted touch of sentiment to the austere daily life of colonial New England. The omnipotent Puritan law-giver, who meddled and interfered in every detail, small and great, of the public and private life of the citizen, could not leave untouched, in fancy free, these soberly promenading Puritan sweethearts. A Boston gallant must choose well his marmalet-madam, must proceed cautiously in his love-making in the gloaming, obtaining first the formal permission of parents or guardians ere he take any step in courtship. Fines, imprisonment, or the whipping-post awaited him, did he "inveigle the affections of any maide or maide servant" by making love to her without proper authority. Numberless examples might be given to prove that this law was no dead letter. In 1647, in Stratford, Will Colefoxe was fined £5 for "laboring to invegle the affection of Write his daughter." In 1672 Jonathan Coventry, of Plymouth town, was indicted for "making a motion of marriage" to Katharine Dudley without obtaining formal consent. The sensible reason for these courtship regulations was "to prevent young folk from intangling themselves by rash and inconsiderate contracts of maridge." The Governor of Plymouth colony, Thomas Prence, did not hesitate to drag his daughter's love affairs before the public, in 1660, by prosecuting Arthur Howland for "disorderly and unrighteously endeavouring to gain the affections of Mistress Elizabeth Prence." The unrighteous lover was fined £5. Seven years later, patient Arthur, who would not "refrain and desist," was again fined the same amount but love prevailed over law, and he triumphantly married his fair Elizabeth a few months later. The marriage of a daughter with an unwelcome swain was also often prohibited by will, "not to suffer her to be circumvented and cast away upon a swaggering gentleman."

On the other hand, an engagement of marriage once having been permitted, the father could not recklessly or unreasonably interfere to break off the contract. Many court records prove that colonial lovers promptly resented by legal action any attempt of parents to bring to an end a sanctioned love affair. Richard Taylor so sued, and for such cause, Ruth Whieldon's father in Plymouth in 1661; while another ungallant swain is said to have sued the maid's father for the loss of time spent in courting. Breach of promise cases were brought against women by disappointed men who had been "shabbed" (as jilting was called in some parts of New England), as well as by deserted women against men.