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Bob has an issue with his phone provider, resulting in the permanent and irreversible loss of his long time phone number which he has maintained for many years. He is greatly troubled and inconvenienced by this, and yet it is not readily apparent how this loss may be quantified even though it is entirely their fault. How could/would such a loss be quantified by a court?

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Given that liability already has been decided in Bob's favor and the question is only about how intangible losses are valued:

Bob would have to demonstrate to the court, with evidence such as testimony and documentation, the nature and extent of this trouble and inconvenience. The court (judge or jury) would then determine subjectively but reasonably what monies, if any, shall be paid to Bob as damages by the phone provider.

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Many kinds of harms are intangible: general loss of reputation due to defamation, harms experienced due to discrimination, pain and suffering after an injury, many torts that are complete without proof of harm (leaving nominal damages as a remedy), etc.

Breach of contract is an example of a tort where nominal damages are available as a remedy.

However, if a judge were to accept that there are material, but hard-to-quantify, intangible harms, they can still arrive at a quantum for an award of damages.

This is an exercise of judgmdent, to be based on reasoned discretion:

In civil liability cases, judges sometimes have the difficult task of quantifying the value of concepts as intangible as a person’s life, physical inviolability or suffering. In this area, where, by definition, the exercise of reasoned discretion remains the rule, the judge must also give as much priority as possible to following established judicial practice while adapting it to the specific circumstances of each case. Because of the essential factual assessment required by this task, an appellate court must take a highly deferential approach to varying the quantum of compensatory damages awarded by the trial judge.

de Montigny v. Brossard (Succession), 2010 SCC 51, at para 27.

In some areas of law or kinds of damages, there is substantial case law establishing factors that should be considered in setting the quantum, and judges should always look to similar cases for guidance. However, in cases of first impression, the judge (or a judge instructing a jury) can do no better than to exercise judgment, with attention to facts that seem salient.

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