As the preceding verse revealed, Paul's plans were tentative to some extent. He wanted the Corinthians to know that he anticipated a return to Corinth and hopefully a stay of several months. Timothy and Apollos might return too.
16:5 At the time he wrote, Paul planned to head north from Ephesus and then spend some time in Macedonia. Macedonia was the Roman province north of Corinth where Philippi, Thessalonica, and Berea stood. He then planned to travel south to Corinth. Paul later changed this plan and travelled directly from Ephesus to Corinth (2 Cor. 2:1; 12:14; 13:1-2) and returned to Ephesus (cf. 2 Cor. 2:5-8; 7:12). Later he visited Macedonia and then Corinth (2 Cor. 2:12-13; 7:6-16).408
16:6-7 Paul did spend the winter in Corinth, but it was the winter after the one when he expected to be there, the winter of 57-58 rather than 56-57 (cf. Acts 20:2-3; Rom. 16:1, 23). He sensed the need to spend a good long visit in Corinth, and in view of the problems in the church that he mentioned in this letter we can understand why.
16:8 The Jews celebrated Pentecost in late May or early June so Paul probably wrote 1 Corinthians in the spring of the year (cf. 5:7; 15:20). It is not unusual that since he was a Jewish believer with the evangelization of the Jews on his heart he would refer to important events in the Jewish calendar such as Pentecost (Lev. 23:15-21). Perhaps the early Christians paid more attention to the significant events in the life of the church than many independent churches do today.409The feast of Pentecost, of course, also marked the coming of the Holy Spirit (Acts 2).
16:9 Paul occasionally used the door as a metaphor for opportunity (cf. 2 Cor. 2:12; Col. 4:3). He stayed in Ephesus three years to take advantage of his opportunities there. He did not regard adversaries there as an indication of a closed door or as a sign that God wanted him to move on to more comfortable ministry. He followed his own advice and remained immovable abounding in the work of the Lord in Ephesus (15:58).
16:10-11 Timothy's visit to Corinth from Ephesus was not very tentative. Paul had already sent him (and Erastus; Acts 19:22) or was about to send him when he penned this epistle (4:17). Evidently Timothy's relative youth tended to make some people despise him, and he tended to be fearful (cf. 1 Tim. 4:12). Paul advised the Corinthians, who judged by external appearances, to give him the respect he deserved for doing the Lord's work as Paul did, not just for Timothy's own sake. We do not know the names of Timothy's travelling companions.
It may have been Timothy's report of conditions in Corinth when he returned to Ephesus that moved Paul to go directly to Corinth himself rather than waiting until he had visited Macedonia. Paul referred to this visit as painful because while in Corinth he encountered strong opposition (cf. 2 Cor. 2:1-8; 7:12; 12:14; 13:1-2).
16:12 This verse may contain Paul's final response to the questions the Corinthians had asked him. It is the sixth instance of that key phrase "peri de"("Now concerning"). Paul's relations with this eloquent brother were perfectly friendly, as this verse reveals (cf. 1:12). We do not know why he did not want to revisit Corinth with Timothy or whether he ever did visit that city again.
