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This paper explores from a Canadian perspective the awarding of damages for non-pecuniary losses that arise in commercial settings and asks the question whether there is any useful function performed by such awards. It is difficult to find cases that support such awards and thus if they are to be awarded, it will be advancing damages for non-pecuniary losses in a new direction. To justify such a movement, I suggest that the any development should be measured by two concepts: legitimacy - what is it that courts can legitimately do, and coherence - how does the award fit into a coherent and predictable legal system.I argue that from a purely compensation point of view, awarding compensation for a loss that is incommensurable does not make much sense. Only if the justification is vindication, deterrence or punishment is there merit in awarding more than compensation, but then, courts or legislatures should develop separate criteria to add quantification and to meet the standards of legitimacy and coherence.