Dear W,

I think your feelings (of being hurt and foolish) show that you aren’t clear what exactly you want from this woman. On one hand, you rejected her advances multiple times: first time 3 years ago, and then again 1 year ago, when you two started working together. You said you weren’t ready for a relationship. In spite of that, you spend a lot of time together and your colleagues suspect you two are dating. But in fact, nothing physical ever happened.

We keep getting closer… It’s kind of a weird relationship where we have discussed if we would date other people and we each have stated that neither one of us is looking for anyone else.

It seems to me that she is as close to you as you let her. She would like to get even closer, but it is you who is hesitating, aren’t you? She said she doesn’t want to date anyone else, that your friendship is the most important thing in her life, besides her children, and that she cherishes every moment you spend together. All this tells me that she is very much into you, and is probably waiting for you to change your mind, i.e. to finally accept her as a romantic partner. Until then, she seems satisfied with being your friend and spending a lot of time together.

But as Helcat said, since you aren’t dating, she has the freedom to go out and do what she pleases. Maybe that evening when she got drunk, she was actually drowning her sorrow in alcohol, because you don’t want to be with her?? OK, I am saying this half-jokingly, but who knows…. specially since later she was embarrassed about it and didn’t want you to find out.

Anyway, she got out with some male colleagues and it upset you very much. You feel “hurt and foolish”. In what way do you believe she hurt you? I think it would be important to get to the bottom of this, to clarify what you really feel for her.