osuche is correct most men will only ask if they know what the answer will be for sure, the best thig to do is just let him know that you are interrested in him and let it go from there. As for the moms boss thing i would not touch that. It can cause a bad reaction if it does not go well which would not be good for the mother. just my two cents and all

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May you live as long as you want, and want as long as you live!!!!!!!!!!!!