Since I'm back in the game I guess its time to do this...story time!

I moved to my current place of residence back in August. I had just gotten my new job and me and my boss were talking here's the convo:

Boss: So Krazi do you have a gf?
Me: Nope, haha
Boss: Huh...how old are you again, 19?
Me: 20
Boss: Oh, my daughter is 20 too, there's a picture of her (in the picture she is EASILY a HB9)
Me:... (unsure of what to say)...Does she go to school?
Boss: Yea, she goes to (the local university), she's going to become a teacher.
Me: Oh nice.

-First time this situation has ever occurred for me so I wasn't on my game...plus its my boss so I was caught off guard completely, haha. And thus began our conversations like this, except its more about him asking me if I have a girlfriend yet, and why not. I always tell him that I just haven't found one yet, and its because I have high standards, I'm looking for a woman not a girl. (which I'm guessing is going all right cuz he keeps asking me if I found a girlfriend.

This next situation happened last month. I had just got fast food with my room mate and for some STUPID reason I decided it would be funny to eat my burger while we walked through the store. Mind you this is the store I work at...so we start walking up to the check stand and I see my boss at the checkstand standing next to these two college girls.

Yup it was my boss' daughter and her friend, and his daughter is a HB9.5 and her friend is a HB9. I'm in sweats, burger in one hand, soda in the other. Perfect time to sarge no?

Boss: Hey Wade! this is my daughter (he didn't say her name) and this is Wade.
Me: (awkwardly balancing my soda on my arm) This is probably the greatest 1st impression you've ever been given. hahaha
Her: Its no big deal, look at me! (she laughed and motioned towards her outfit...which was sweats and a hoodie)
I felt as if I already failed so I didn't really say anything after that. Me and my room mate left the store and his daughter and her friend circled the parking out to check us out (couldn't have failed too badly eh? lol)

So here's the facts:
-His daughter is single
-My boss likes me enough to try to hint or whatever you want to call it that his daughter is single, introduce me to her (and introduce me to district managers, people of importance at my job)
-My worst 1st impression wasn't too bad.

And here's the dilemma: I have no idea how to do this. I have my natural game down pat. If she were to come in the store I wouldn't have a problem. But she doesn't. I don't know whether to be straight up and give my boss my number for her, ask what is daughter is up to, or what.

Any suggestions?

Thanks in advance guys.
-Krazi

I would NOT!!!!! NOT!!! (in case you missed it NOT!!!)

NOT!

sarge my boss's daughter under any circumstance!

First off a few quick questions. Is this a long term job or just a momentary deal? If it's the second then you can continue. Only you have to manage two sets at once if that makes sense. The first is the daughter, spit whatever game you have at this point and assume it's going to work, but be genuine about it; the second is the boss. The boss is not going to want to hook his daughter up with a PUA. You're going to need to show this man a constant stream of DHVs mixed with genuine interest. Guys can smell a player from miles away, you know it and I know it; so just be fluid. It's really up to you though, I wouldn't go for the boss's daughter unless I knew it was relationship material or could progress to that. Unless the girl is overly sexual and you know she wouldn't talk to her folks about you it's a big risk. You said she has a cute friend, maybe make buddy buddy with the daughter while macking the friend. This will show DHVs to the daughter while leaving it open. Really though it's up to you, do you actually WANT the boss's daughter or is she just another mark.

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"All the dragons in our lives are perhaps princesses expecting us to be handsome and brave, all the terrifying things are perhaps nothing but helpless things waiting for us to help them." Rilke