Forgiveness/Judgement Relationship

At Ladner United, Jim Short derived this morning’s sermon from the event ten years ago today but focussed his thoughts on forgiveness. He drew upon an event in his own life that challenged his own capacity to forgive. That example drew me into some challenging thoughts about forgiving.
The first stems from the simple recognition that to forgive a right-doing (or non-indebtedness) is an offensive absurdity. Thus every deliberate act to forgive implies a judgement of wrong-doing (or of perceived indebtedness). Christians are called to forgive, yet one of the most widely held criticisms of Christian practice claims that we are too judgemental.
Corollary to this, the second involves the question never asked of Jesus of when to forgive. Must the person to be forgiven acknowledge the wrong (or indebtedness) before forgiveness gets extended? I tend to think not necessarily. Yet I can think of an example of two close childhood friends who, as they matured, began to drift apart. The first did something that offended the second. The second, determined that the incident should not disrupt their friendship, immediately forgave the first. The first found this forgiveness offensive, “I have done nothing wrong for you to forgive,” and that friendship broke irreparably. Forgiving should heal relationships but does not always do so.
Further thoughts on the relationship between forgiving and judgement will be most welcome.