I tried it with Python2.7 and Python3 in Visual Studio 2019. In both cases the plot window freezes if I use plt::show(false);. Just plt::show(); works for me.
E.g. the following does not work:
std::vector<float> test_values = { 1.0f, 3.0f, 2.0f };
plt::plot(test_values);
plt::show(false);
while (1)
{
}