OK so a little background info

There is a girl at my job that works with her mom and family as part time cleaners. she's cute and over the last 3-4 months i have slowly built a rapport and im one the only few guys she speaks to when she's there. now the problem with asking her out is that her dad is my supervisor. a few months ago a guy at work who she liked asked her out but she told him that he would have to ask her dad (my boss) for permission to date her. the guy had no frame and pussied out and never spoke to her again since he was scared to ask for permission.

now im definitely interested in seeing her outside of my work but i know that if i ask her out she'll hit me with the "ask my dad" shit test. now i need advice on how should i proceed with this. should i ask my boss in advance or should i just bite the bullet and ask her and see if she does make me ask her dad. I want to be able to cover all my bases before i make my intention to court her serious and i think if i have already asked her dad she will see me differently than the other guys who have tried to court her and have all been too scared/weak to seek permission from her father.

oh and yes i do have a good working relationship with my boss we're pretty good friends and we talk a lot about things not related to our work. i really trust him and look up to him as a role model and we have a good friendship.