Attn: Inquiry for mentally mature females?

I would like to pose a question for the mentally mature females but real men with insight into this could jump in. So let me give some backdrop.
I got a job and my boss is a "friendly" woman. Think Joan from "Mad Men". She's gawked at a TON. Flowers, candy, cards from guys everyday because of it. I thought she was attracted to me but I was wrong.
She can't have me anyway because I like her friend (we all work in the same building) and I asked her friend out but her friend said no. Then, her friend told on me to my boss. The next day, my boss threatened to fire me since I was still in my probationary period and that kind of thing was frowned upon.
Asking a female out? I've done it thousands of times. What gives?
My friend told me that the female that I asked on a date said that I was too aggressive. I think it might be because she's 48 and I'm 29... or she's right and I've just been getting by on looks this whole time and now I have to actually get good at asking girls out because this is the "real world".
How can I fix this or should I just quit?

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What Girls Said 1

  • The age difference is probably the main part of the problem. It's almost 20 years, and dating a co worker is sometimes not approoved of in some businesses. I think that if you really have feelings for that woman to go for it, but keep in mind that the situation could cause you to lose your job. I hope everything works out for you.

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