Well, shes not really my boss to be honest. Really shes the boss' sister. Shes a HB8 i would say. But shes involved a lot in the academy, and has considerable authority.

Now before anyone says anything to change my mind, I just wanna point out a few things.

1. All's fair in love and war.
2. I honestly dont give a shit about my job, so dont shit where you eat doesnt count. Im already focused on another money-making project which will be better for me. Basically I'm still sticking with them because a) they dont want me to leave bc im a good worker, and i can exploit that, and b) I meet lots of cute girls at this job. Which is where most of my game comes from.

So anyways, when I first met her, i honestly didnt know she was anyone with authority. I saw her and assumed that she was a new employee. I just saw hot girl and approached. I gave her a VERY powerful first impression, and it seems to have had SOME effect. Now its hard to tell if i have gotten any IOIs from her, given it is a professional enviroment, and getting with her is different than getting with the other girls who work there. For that reason shes less likely to advance on me like the other girls have. However I have this gut feeling that I can play this game. That being said, I definitely stand from the crowd, not only in her eyes, but also, but her brother's as well. However my work ethic has a lot to do with it. However my personality does as well. I don't kiss ass, and I stand my ground, however i get the job done, and well.

Now for the advice, obviously building TONS of rapport should be priority number one, which is easy cuz she is very open to casual convo. Getting close to her brother is also important. However thats a given, as getting close to her brother is necessary for another of my objectives. I figure the best way to handle this would be like trying to get with a married woman who isnt polygamous (which I also havent done, but its an interesting way to frame things), I guess think what would Bond do. I also have to demonstrate value beyond my personality. Demonstrate independence, especially from the business, to therefore also demonstrate a "willingness to walk away," i figure talking about my goals is the best way to do this.

Now as to why I am doing this. Well when i first realized who she was, i was attracted to the idea. The challenge of this game called me. I wanna see if I can do it. My pride I guess. And now, t seems she will be spending more time in our branch. So the opportunity to game her is definitely there.

Anyways, advice is definitely appreciated, I wanna know what you guys think of this, and some protips from those of you who have tried something similar.

Cheers

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"Be the change you wanna see in the world" -Gandhi

You may think that, but they can easily think you are using sex as a barging chip to stay there. Now unless you are a key person of this company they are very well can replace you like that. I am not saying you can't, but more pointing out a very likely possibility here.
Not sure what this has to do with anything.
A balance here is very very very important here. Because just because you don't care about this job, that in no way means what you do here can backfire on you later on in life it being personal or in your upcoming business adventure. So while it is easy to say tread carefully, if you do it too carefully you not close the girl, hence the reason why the balance is so important here. Saying that, I will not go the Bond route here. Expressing your business goals will help you, but not expressing your willingness to want to walk away. If you do that depending on what you do you may be replace in an instant.
Why do you feel to explain why? If you have no moral/ethical issues with this then why explain your self?
I never hit on my boss or their family members. Tho I have hit on some of the more powerful women at my work tho as well girls that know my higher ups.

im explaining myself to avoid the "dont do it," or w/e replies, i mostly seek advice

I never hit on my boss or their family members. Tho I have hit on some of the more powerful women at my work tho as well girls that know my higher ups.[/quote]

how did that go? im sure its similar to my situation, bc like i said, she isnt exactly my boss, but yes a higher up...[/quote]

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"Be the change you wanna see in the world" -Gandhi

DON'T

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"I am the greatest, I said that even before I knew I was."

why not?

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"Be the change you wanna see in the world" -Gandhi

Pretty well. Only have gotten as far as a kiss. But that is really as far as I am willing to push things.