The second of the four steps of teshuvah is easily said, but not so easily accomplished, regret for one's past sins. To understand Rambam's view of this step, we should note that he refers to these steps in each of the first two chapters of Hilkhot Teshuvah. As the Rov, ztllh"h, noted in Al haTeshuvah (available also in English as "Rabbi Joseph B. Soloveitchik On Repentance, edited by P. Peli, and fine synagogue reading for the High Holidays), in the two presentations, the 2^nd and 3^rd step are in different orders.

The Rov builds a beautiful discussion of two different types of teshuvah-- the intellectual and the emotional-- in which the order of the regret for the past and the decision not to sin in the future (the third step, which we will discuss, be"H, next week) would be reversed. In some teshuvah, the person decides not to commit the sin again for intellectual reasons, a logical assessment of the pluses and minuses of sin. In other cases, the person's revulsion for the sin leads to the teshuvah. In the first type of teshuvah, regret would only come with some distance from the sin. When the person decided not to sin in that way anymore, the sin had not lost any of its attractiveness, so there is no reason the person would have learned to regret the sin committed. Only after a while of a righteous life would the person come to appreciate the problems in sin, and regret them.

In the second type of teshuvah, however, at least part of the motivation to repentance is a recoiling from sin; in that situation, the regret for the past comes before the acceptance for the future.

The Rov's notion explains another difference between those two presentations, their view of the role of embarrassment in teshuvah. In the first perek, when Rambam gives the proper form for vidui, confession, (which we will discuss, be"H, in two weeks' time), he mentions the person saying "nihamti u-boshti be-ma`asai, I have regretted and been embarrassed by my actions"; in the second perek however, he simply says that after having decided not to commit the sin anymore, the person will regret the past. Embarrassment is apparently not a factor.

Using the Rov's notion, it might be that our ability to be truly embarrassed by our sins depends on the underlying motive of our teshuvah for those sins. Those who repent a sin out of their realization that it was a trespass against the Lord (or in some other way come to grasp its enormity) will only regret their act, an expression of an awareness that a certain act was not productive, a waste of energy, or some such. If, however, the teshuvah stems from a sense of the horror of sin, the sinner will not only regret the past, he will be embarrassed about it. In that version, therefore, Rambam mentions nihamti u-voshti, I have regretted and am embarrassed.

I would note that R. Yonah includes not only embarrassment (and means a physical embarrassment, such that he would be happy if a person would physically blush when recalling his past sins) but also distress and anguish. For him, in other words, teshuvah is not only about removing sins from one's life (which would only require recognizing sins and deciding not to commit them anymore), it is about developing one's sense of revulsion for sin, a sense that is heightened by regretting one's own sins with a sense of embarrassment in addition to simple regret. There is also a difference in the role vidui plays in each of these processes, but we will leave that for our discussion of vidui.

Here, however, we should pause to bring the discussion into the realm of the practical. How should we conceive of our sin? As a step of teshuvah, regret-- regardless of whether it is intellectual or emotional-- means that we recognize that what we did was wrong, and are saddened by having done it. We sometimes hear people who, in thinking of their past, will know that they no longer wish to act a certain way, but still have fond memories of the times when they did act that way. Such people have certainly not attained regret of their past sin, since regret means a sadness over the distance from God created by certain of our actions.

Other times, I have heard people say, "well, that was who I needed to be then, and was part of my growing to where I am now." That view comes closer to regret in that it does not see the acts as positive, it just recognizes that those acts were a function of who the person was at the time. Nevertheless, my understanding is that teshuvah also involves a certain sadness over who we were then. It may or may not have been necessary for us to act that way (the notion of free will should mean that it is never necessary that we sin), it may or may not have been the best representation of who we were at the time, but we should still regret who we were then. Part of teshuvah, in other words, is not just recognizing that we violated a law on the books and have to pay some penalty (or avoid it by this penitential process)-- it's that we are saddened by having done so and we see that that act worked to our spiritual detriment.

To achieve that kind of regret, however, we need to be willing to feel the vulnerability of being wrong, to accept (internally) the blame for having mishandled our lives. Many of us react defensively to such a notion, and therefore reject the need to say that we were wrong, that we are saddened by the wrong actions we took. Part of teshuvah, however, is overcoming that defensiveness, and seeing where we have acted wrongly, and being saddened by it.