Why does the compiler choose bool over string for implicit typecast of L””?

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First, the cause of this issue: C++ Standard [over.ics.rank]/2.11 defines an order for conversion sequences. It says that a user defined conversion sequence is worse than a standard conversion sequence. What happens in your case is that the string literal undergoes a boolean-conversion (defined at 4.12. This is a standard conversion). It does not use the user defined conversion to std::wstring which would be needed if it took the other overload.

I would recommend to simply change the name of one of the overloads or adding an overload that accepts the string literal directly (using parameter type wchar_t const*).

1)

When comparing the basic forms of implicit conversion sequences (as defined in [over.best.ics])

(2.1) a standard conversion sequence is a better conversion sequence than a user-defined conversion sequence or an ellipsis conversion sequence, and
(2.2) a user-defined conversion sequence is a better conversion sequence than an ellipsis conversion sequence.

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