I’m not sure that Tshuva has much to do with forgiving. Or, at least, our forgiving, and I’d argue that we shouldn’t pro-actively forgive anyone who’s truly harmed us before they ask. Not to be disrespectful, but that sounds a lot more like “Turn the other Cheek” Christianity, which is so understandable since most of us grew up under a mixed fabric of Judeo-Christian Ethics, which for all it’s fancy title, really had little to do with traditional Jewish values and teachings.

In terms of Halacha, we’re supposed to ask forgiveness from everyone we harmed over the past year. Once asked, although we’re not commanded to, it’s advised that, given certain criteria, we do forgive. But I would argue that forgiving someone who hasn’t actually asked you, rather than being generous, steals the mitzvah of asking from them. It reminds of of how my great teacher, Rabbi Shloime Twerski zt”l would never let someone walk through the congregation with the tzedaka pushka even though that’s standard practice in almost every shul I’ve ever been in. He felt that at least part of why someone would give in that situation is because someone is standing there, asking, rather than walking up on your own because your heart calls you to give.

In another directions, we’re instructed to try to imitate The Creator, and The Creator will always forgive (but only if it actually benefits the one who’s asking—blanket “amnesty” can encourage people to “sin” because they know it will be wiped away….). And My ways are not your ways—we aren’t equipped to understand why God does anything.

The subtleties of Chazal, our sages, are so deep.