walkingdork said:

(okay so here's the actual conversation part)

So we are hanging out at the same bar as before and she says out of nowhere, "I like large penises." It was like she couldn't wait to get it out there. She continued and said that she has been lucky when it comes to men with big dicks. So not knowing how to act towards such a statement I just say, "Well Baby, your luck has run out."

Wait, what? Is that really that weird? I mean, you guys hung out before and she made it clear she was sexually interested in you, and you still hung out with her again, which naturally would suggest to her that the sex thing isn't off the table. Add a little alcohol to the mix, and talk of genitals seems like a fairly reasonable topic for conversation.

I take it the weird part is she simply assumed you have a large penis without having any reason to suspect it?

Which part exactly is "goofy shit"? Just the fact that she so blatantly wants to have sex with you, or the penis conversation?

As far as the two Daves' sentiments about just going for it, I most definitely see your hesitation. 21 is really young and she sounds kind of immature. I wouldn't be opposed to having a casual sexual relationship with a co-worker, if it could be just that. But at 21, the chances of that going over without out-of-control drama in both your personal and work life seems much less likely.

So now I'm in this super awkward situation and I have no idea how to handle it. She is my coworker after all.

With tears in your eyes and a shameful quiver in your voice, tell her you have a really, really, really tiny dick, and that after her comment about liking big penises, you'd be too ashamed to even try it for fear that she wouldn't even be able to feel it. From there just tell her you'd like to keep things professional. ;-)