Then come his friends, interested in his physical and spiritual welfare, and realizing that it is not well for man to live alone, they begin to urge upon him the benefits of wedlock.  “March 14, 1717.  Deacon Marion comes to me, visits with me a great while in the evening; after a great deal of discourse about his Courtship—­He told [me] the Olivers said they wish’d I would Court their Aunt.  I said little, but said twas not five Moneths since I buried my dear Wife.  Had said before ’twas hard to know whether best to marry again or no; whom to marry...."[238] “July 7, 1718....  At night, when all were gone to bed, Cousin Moodey went with me into the new Hall, read the History of Rebeckah’s Courtship, and pray’d with me respecting my Widowed Condition."[239]

Thus urged to it, the lonely Judge pays court to Mrs. Denison but she will not have him.  Naturally he has little to say about the rejection; but evidently, with undiscouraged spirit, he soon turns elsewhere and with success; for under date of October 29, 1719, we come across this entry:  “Thanksgiving Day:  between 6 and 7 Brother Moody & I went to Mrs. Tilley’s, and about 7 or 8 were married by Mr. J. Sewall, in the best room below stairs.  Mr. Prince prayed the second time.  Mr. Adams, the minister at Newington was there, Mr. Oliver and Mr. Timothy Clark....  Sung the 12, 13, 14, 15 and 16 verses of the 90th Psalm.  Cousin S. Sewall set Low-Dutch tune in a very good key....  Distributed cake...."[240a]

But his happiness was short-lived; for in May of the next year this wife died, and, without wasting time in sentimental repining, he was soon on the search for a new companion.  In August he was calling on Madam Winthrop and approached the subject with considerable subtlety:  “Spake to her, saying, my loving wife died so soon and suddenly, ’twas hardly convenient for me to think of marrying again; however I came to this resolution, that I would not make my court to any person without first consulting with her."[240b] Two months later he said:  “At last I pray’d that Catherine [Mrs. Winthrop] might be the person assign’d for me....  She ... took it up in the way of denial, saying she could not do it before she was asked."[241a]

But, as stated above, Madam Winthrop was rather capricious and, in popular parlance, she “kept him guessing.”  Thus, we read: 

“Madam seem’d to harp upon the same string....  Must take care of her children; could not leave that house and neighborhood where she had dwelt so long....  I gave her a piece of Mr. Belcher’s cake and gingerbread wrapped up in a clean sheet of paper...."[241b]

“In the evening I visited Madam Winthrop, who treated me with a great deal of courtesy; wine, marmalade.  I gave her a News-Letter about the Thanks-giving...."[242]

Two days later:  “Madam Winthrop’s countenance was much changed from what ’twas on Monday.  Look’d dark and lowering....  Had some converse, but very cold and indifferent to what ’twas before....  She sent Juno home with me, with a good lantern...."[243a]