They both had Abigails, born about the same year.
"Genealogical Dictionary of First Settlers of New England, Before 1692" by James Savage states:
MATTHEW, or MATTHIAS, Middletown, the freem. of 1657, may have been br. of James, certain. call. serv. of Richard of Wethersfield, 1645, or soon aft. m. at W. 1648, Mary, d. of the first Richard Smith of the same, had Henry, b. 1649; Susanna, 1651; Richard, 1655; Elizabeth 1657; Abigail, 1659, wh. m. 1683, Stephen Hollister; and Dorcas, 1661; and he d. 1662. His wid. m. Anthony Wright.
*ROBERT, Milford, s. of the first Richard, b. in Eng. had liv. with his f. at Wethersfield, ...[snip]He had two ws. Jane, only d. of Edmund Tapp, wh. d. 8 Apr. 1703; and he m. 22 Oct. 1705, a wid. Elizabeth Bryan, wh. d. 10 Jan. 1706... [snip] Samuel, bapt. 3 Sept. 1648, H. C. 1669; John, 20 Oct. 1650; Mary, 23 May, not 28 [snip]; Robert, b. 14 Aug. 1654; Sarah, 9 Oct. 1656; Hannah, 1 Jan. 1660, wh. m. Rev. Samuel Mather of Windsor; Joseph, a. 1662; Abigail, wh. m. Rev. Samuel Andrew of Milford.