The article defines the overconfidence as a belief in an outcome despite what reasonable past statistics tell us. "the kind of optimism that leads governments to believe that wars are quickly winnable and capital projects will come in on budget despite statistics predicting exactly the opposite." On a second thought, project planning and making plans in general that involve duration, cost, etc, and "asking a girl out" or "asking for a pay rise" are very different things and I'd prefer not to conflate the two.

You might be able to generate some stats on what % of girls that are asked out (in some particular circumstantce e.g. at a bar in Kentucky, etc) agree or how many pay rises are approved. You can then talk about over- or under- confidence if expectations of the outcome deviate largely from these stats. How much is too little or much? Who knows.