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So first of all - don't shit where you eat.
We've all been there and done it. It's a bad thing.
Why are you doing pickup in your office - where you could be fired or disciplined for breaking HR regulations, creating conflicts of interest, and just plain making things uncomfortable for yourself when things go south with a woman you work with?
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But if I go direct, then it seems girl will think that this guy is approaching girl in office, which means he is not able to get girl outside office, which means he is pathetic.
Where did you hear this? That's horse shit.
Game outside work, dude.
I think he is looking for advice how to game outside of work because he feels its harder to find a common topic.
Even though he is shitting where he eats it may not be that bad being that he is working in a building of 10k as opposed to 100 so assuming the female isn't working in the same department as him he wouldn't come across her often.
I say go for it just socialize with them become friends it wouldn't hurt, but thats up to you if you want to go that step further with your coworkers. I personally don't care I game where ever and even when things didn't go well with my coworkers we we're able to maintain a professional relationship or at least not have an awkward vibe between each other.