Even if you’re not as old as I am, you may remember Frank Sinatra's “I did it My Way,” with the familiar line: “Regrets, I’ve had a few, but then again, too few to mention.” Of course everyone knows no one can live without regrets. The Bible abounds with regretful people. ‘Regret’ is an unhealthy feeling of sorrow about something that one wishes could be different; and that kind of sorrow can control one's life.
In Paul’s 2nd letter to the Corinthians, he speaks of two sorrows: there is self-oriented sorrow (the result of unresolved regret); and there is a God-initiated sorrow (leading to repentance and freedom). “The kind of sorrow God wants us to experience leads to salvation. And there's no regret for that kind of sorrow. But worldly sorrow, which lacks repentance, results in spiritual death” (7:10).
Two disciples with the most to regret were Peter and Judas. Peter’s sorrow led to repentance. But Judas’ sorrow led to death. Certainly Jesus would have forgiven Judas had he repented! Or for that matter, Frank Sinatra, who could have sung, “Regrets, more than a few; but then again, no need to mention.”