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Greatly desiring to see thee, being mindful of thy tears, that I may be filled with joy;

New Defender's Study Bible Notes

1:4 thy tears. Timothy evidently had wept when he heard of Paul’s imprisonment (probably his second Roman imprisonment—see note on I Timothy 1:3) and coming execution. Paul himself was frequently moved to tears on behalf of those whom he was trying to help (e.g., Acts 20:31; Philippians 3:18). John also wept (Revelation 5:4), and so did Jesus (John 11:35; Luke 19:41). There is, indeed, “a time to weep” (Ecclesiastes 3:4).

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