@MasterSimper First off, this "sister group" is in the same employer, correct? This is going to be the first cause of concern if you have an interest in this woman. Which is too bad, because the other parts of the story tell me there is mutual interest.

Some employers have explicit prohibitions on fraternizing, and if that is the case with your employer, you cannot go further. There might be other policies to consider too which could put you in a bad situation.

@MasterSimper Your first priority is to avoid any problems like this. If that means nothing further can come of your encounter, then you might have to accept that. Outside of that situation, I would be upfront with any intentions you would have. OUTSIDE OF WORK, there is no reason to not just lay out what you are wanting. If a woman does not want what you want, she can let you know and you can go your separate ways. It saves everyone time.

@MasterSimper Again, the advice of "don't shit where you eat," should be the first priority. If she were to press the issue, just be upfront about you having a policy of not dating anyone you work with, and that it is nothing against her personally (if that is indeed the case).

I cannot tell you play by play what to do, but I express that you should be cautious when it comes to workplace related things like this.

@MasterSimper Okay, the next thing to consider is not just prohibitions, but also consequences of any relationships within the workplace. If any relationship goes south, you may have some awkward times in the workplace going forward. And the worst case scenario is false accusations against you.

Not saying that will happen for sure, but it is important to be aware of the risks.

Again, I cannot know the whole situation you are going through. I just am expressing caution.

@MasterSimper Putting aside the whole work thing then.

The purpose of being upfront is to not waste time or opportunities. There is no magic moment when a woman is going to be more likely to reciprocate interest, she already will know what she wants. You simply find out faster where you stand.

It also helps you from feeling heartbreak if you are rejected. Waiting longer just means you are investing more time in a woman before you even have a relationship.

@MasterSimper If a woman was going to reject your advances when you ask, you just figured out that she was not interested in you that way. If she says yes, you get to move forward with things.

This principle also works for escalating a relationship to more serious stages. If she were to be put off by the idea of taking the relationship further, then you just saved yourself time and energy by not keeping with a woman who is not ready to be serious when you are.