Among these difficulties are the following: 

(1.) Whoever carefully studies these three epistles in their connection with each other, and in contrast with the other Pauline epistles, must be profoundly impressed with the conviction that they all belong, as it respects style and tone of thought, to the same period of the apostle’s life; and, as it respects subject-matter, to the same era when the churches were troubled by the same forms of error.  But if we assume that they were written during that part of Paul’s ministry of which Luke has left us the record, the second to Timothy must be widely separated from the other two.  That was certainly written during Paul’s last imprisonment near the close of his life.  But when he wrote the first to Timothy and that to Titus he was at liberty and prosecuting his missionary labors in Asia Minor and the vicinity.  It must have been then, upon this assumption, during his third missionary tour (when Apollos appears for the first time, Acts 18:24 compared with Titus 3:13), and before his last recorded journey to Jerusalem, his arrest there, his two years’ imprisonment at Cesarea, his voyage to Rome, and his imprisonment there for the space of at least two more years.

(2.) There is no part of Paul’s history “between his first visit to Ephesus and his Roman imprisonment, which satisfies the historical conditions implied in the statements of any one of these epistles.”  Conybeare and Howson, vol. 2, Appendix 1.  The student may see the arguments on one side in Davidson’s Introduction to the New Testament; and on the other in Alford, and other critical commentators.  Reference may also be made to the biblical dictionaries.

(3.) Upon the assumption that the first epistle to Timothy, whom Paul had left in charge of the Ephesian church, was written before his recorded imprisonments at Cesarea and Rome, it must be earlier than his farewell address to the elders of Ephesus, and also his epistle to the Ephesians.  But the contents of the epistle manifestly point to a later period, when the errors in doctrine and practice which he had predicted (Acts 20:29, 30), but of which he takes no notice in his epistle to the Ephesians, had already begun to manifest themselves.  The more one compares with each other these two epistles, the deeper must his conviction be that the first to Timothy is not the earlier but the later of the two.

(4.) The peculiar tone and diction of the pastoral epistles and the peculiar character of the errors combated in them all indicate a later period in the apostle’s life, and a later stage in the history of the churches.  To place the first and third of these among those to the Galatians, Corinthians, and Romans, and the second, among those to Philemon, the Colossians, Ephesians, and Philippians, must appear forced and unnatural.  It is much easier to assume the lapse of some years.  Even then the contrast between these