Robert Stiles apparently married a second time and her first name was Elizabeth .........? It is likely that Samuel 2 Stiles was born of this union.

Robert Stiles of Dorchester, Mass., is first mentioned as the purchaser of land in that town, in 1659. In the fall of the following year he married, and became a householder, and in 1683 was obliged to pay the penalty for entertaining strangers contrary to law -- a fact which does not speak well for his character as a citizen. In the year 1666-7, his name occurs among those who received grants of village lands in Rowley, and in 1673 he, with four others, petitioned the General Court, praying that they might be set off to the adjoining town of Topsfield. Stiles and his fellow-petitioners were at this time residents of Rowley Village (now Boxford) about six or seven miles from old Rowley, and as it was much nearer for them to attend church at Topsfield than at Rowley, they preferred to pay their ministry notes to the former place. This however was denied them. In 1670 Stiles sold his property in Dorchester to Edward Payson of that place. In 1672, he was called before the selectmen of Dorchester "to answer for idleness, and it was found that neither he nor his wife improved their time, as they should". Yet, the admonition which they doubtless, received from the worthy magistrates, on that occasion, does not seem to have been heeded, as in 1679 the records of that town inform us that "Robert Stiles was called before the Selectmen to give an account how he improved his time: also the same in relation to his children. The conclusion was that he should look out for a place for his children, or the Selectmen would provide one".
In 1680, he is mentioned as among the recipients of the legacy left by Mrs. (widow of) John Birge, for the poor of the town of Dorchester--which bounty was that year distributed in shoes. In 1684, the Rev. Joseph Capen was settled at Topsfield, where a church had existed since 1663, and in his list of "members in full communion" at the time of his ordination, we find the name of Robert Stiles, as also (subsequent to his ordination) those of his son John, and Deliverance wife of the latter, and under date of February 23, 1689, the name of Elizabeth Stiles. During the year 1685 the town of Boxford was formed, and the Stiles family afterward appear on the town and church records. In the old Burying Ground at Dorchester, MA., is the gravestone of Robert Stiles, aged about 91, died November the 2nd 1710.

The first volume of the Records of Births in Essex County, Massachusetts, at the Clerk of Courts office at Salem, contains the record of births, marriages and deaths from 1654-1691, inclusive, among which are the following:
"In Rawley, Robert Stiles and Elizabeth (daughter. of John) Frye, married the fourth of October, 1660".