It has been about five years since I've gone to somebody in the days before Yom Kippur and sought forgiveness for my specific sins against them. I've never experienced the healing and reconciliation this can bring.
I'm skeptical of seeking of forgiveness unless it meets these criteria:
* It is for something specific where one can take practical steps to mitigate the harm one has caused.
* The seeking of forgiveness can do some good and lead to a reconciliation. Most of the relationships that have ruptured in my life have been irreparable, not so much because of the hugeness of the sin, but because we've been going in different directions, and our differences in direction are irreconcilable.
My best friend in Los Angeles had bad credit. I gave him a credit card in my name (I was responsible for paying for it). He was usually late paying me. Finally, I cut off his card. He refused to pay me the approximately $400 he owed me. We've never been able to discuss the matter. I've tried a few times (pushed by my therapist) but he would never talk about it. He has no money. I can't forgive him because he hasn't asked for forgiveness. Every time I hear his voice on the phone (I decided to keep him as a friend because I can't afford to keep chucking people out of my life), I remember how he didn't repay me. Our friendship limps along.
I remember once (in 1990) I sought the advice of a rabbi on the day before Yom Kippur about my long distance telephone-and-letter relationship with a non-Jewish ex-girlfriend. He told me to cut it off. I knew he was right. I did. It caused pointless misery for both of us. She'd already moved on to another relationship and she just wanted to stay in touch with me because I was so sick, lonely, and isolated.
Most every time I pushed myself to act extra-moral, I only increase my isolation. Plenty of my immoral acts have also furthered my isolation. On balance, my immorality has hurt me more than my putatively moral acts.
Cathy Seipp and I have exchanged numerous barbs over the length of our friendship, many of which have hurt the other. But it would feel pro-forma to me to go to her and ask for general forgiveness. If I ask it for specific wrongs, that would only increase the hurt. So forget it.
Most of the hurtful things I say, and that people say to me, are true, and much of the time they impart needed truths. Hurting somebody is not always wrong. Hurting somebody needlessly, for no good reason, is wrong.
I've often done the 'please forgive me for anything I've done against you in the past year,' which, without specifics, feels pro-forma to me (but I always reciprocate it if somebody offers it to me). I normally try to apologize as soon as I realize I have done wrong against somebody (when I think the apology will do some good).
In my experience, most apologizing is pro-forma and rarely does any good. Not apologizing for needlessly hurting somebody, however, is a horrible thing.
Most of my sins over the past year have been careless remarks which have wounded feelings and tasteless writing on my Web sites. So, dear reader, please forgive me for the awkwardness, shock, horror and disgust your reading of me has brought you, your family and your community (I know you can not forgive on behalf of others).
