The problem occurs when considerations of work done are generalized to considerations of energy. There is nothing wrong, for example, with saying that 2500 joules of work is done by the boy on the dresser, which is of course equivalent to saying that -2500 joules of work is done by the dresser on the boy. This is nothing more than saying that when 2500 joules of work is done on the dresser, -2500 joules of work is done by the dresser.
Problems occur when we make statements about energy transfer, like saying that 2500 joules of energy was transferred to the dresser by the boy. Such a statement is valid only if the dresser can be modeled as a particle, unable to absorb internal energy and undergo a temperature change. For example, if the dresser moves at a steady speed the 2500 joules of work done by the boy on the dresser may not constitute a transfer of 2500 joules of energy to the dresser, some of that 2500 joules may be transferred to the dresser, increasing its temperature, but the rest may be transferred to the floor raising its temperature. And statements such as the work done "goes into heat" are also incorrect, as in this case there is no transfer of heat, the process is adiabatic.