Hi Jessa,

In a lot of ways, you have already answered your own question in that you know you will regret it if you don’t ask and there is absolutely nothing to be gained for not asking (while asking will present the opportunity for employment). Yes, it’s true that he may say no and if that’s the answer, it will be heart breaking and soul rendering but this pain is still far less than the disappointment you have in yourself for not asking. As an adult, do you admire someone who tried, failed but kept trying or someone who gives up before trying? Be the person you admire and you will build your confidence no matter what the outcome is for this encounter.

Oh and if it helps, we are usually more critical of ourselves than anyone else in the world. So you might think that he’s seen you at your worst but it’s highly likely that it’s not as bad as you thought.