| I'll make this one quick.
Last week, HB9 comes running to the elevator as it closes and we are the only ones on it at the end of the work day. We start out with some general chit chat and I ask her why she stopped coming to certain meetings she used to in our department, etc etc...
She starts immediately shit-talking the company, which makes me laugh because we are in 100% agreement so we are talking about those things on the way to the parking lot... I feel like she is giving me IOI since she is more or less a stranger (I've never really talked to her before) and she is totally opening up to me with shit you wouldn't really say to someone at work you don't know (because what you say to the wrong person may end up costing you your job if you aren't careful).
We get to the point where we need to part ways and I am moving with my body language towards my truck, and she keeps the conversation moving and keeps me there standing with her talking for another minute or two.
I took it as an IOI but was too chicken shit to pull the trigger and ask her out, this was unexpected and I didn't know if I should ask her out for drinks right there, lunch tomorrow and my best friend's advice "Don't dip in the company pool" certainly popped into my head.
But I've always thought this girl was the 2nd hottest girl at work and the #1 slot is happily married with kids, so she is the #1 AVAILABLE girl hahaha.
I decide that if I run into her in the hall and we are alone I am going to definitely ask her to go out for drinks or lunch or something of the sort.
Fast forward a few days...
Today — I am coming back from lunch. I see her from a distance, and we lock eyes and she immediately gets this big grin on her face and she even waved to me from across the way.
I think my intuition is telling me there is definitely something there, and that seems to be a little more friendly than your average "hey" as you cross paths with someone in the office.
My options are either WAIT until another opportunity to cross paths with her and flat out ask her out because the opportunity may never come again (and I should have had the balls to do it the first time)…
OR
I thought about just sending her an email saying "XXXXX has their milkshake happy hour today, and we all usually go, but nobody wants to go today so would you join me? blah blah blah… If so, meet me down in front of the building at X:XX o clock!"
Now, with that said — would it be WAY too creepy to just email this girl out of the blue and ask her to go out for a treat this afternoon (or tomorrow, or whatever)?
Pros: Could get this moving today, as in RIGHT NOW
Cons: Could blow myself out and become "the creepy stalker guy at work"
Or would it be better to wait until the off-chance I DO run into her in a situation where everyone we work with aren't around so I can pull the trigger without everyone else at work being up in our business?
Pros: Takes more balls to directly ask a girl out face to face
Cons: Could take weeks before the proper situation presents itself
Obviously if she DOES like me then she would probably be HAPPY to get an email like that.
This would not even be a dilema if not for the fact we do work at the same company and I am very hesitant to dip in the company pool.
The last time I did THAT shit I worked at Burger King in HIGH SCHOOL! And yeah, that shit became awkward even in that grease pit!
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