How to make it work this time- And how to ask her out again
 

So there's this amazing woman. I've been blessed enough to know her for nearly three years now. Some of that time, we've been partners. Some of it we've been enemies. Most of it, we've been friends. Fourteen months ago, we made an agreement we would put our feelings for one another on the back burner, so to speak, so that I could get my ducks in a row and figure things out. Fast-forward to present day, and I've got things pretty well figured out. I am in a much healthier place emotionally then I have ever been. I have my issues, but I work terribly hard to overcome them every day, and each day I am working towards a happier, healthier future. And it's come to the time where I feel I may finally be ready for something with her.

For a long time I avoided talking about things with this woman. For one, she's often very busy. For two, we're involved in a rather complicated relationship situation in which I have long-standing resentment and anger towards someone she is extremely close to, and I struggle with that sometimes. For three, I'm terrified of getting things wrong. This would be the third try. We both know that this is the last try we have in us, and although I am so much better and know deep down I could handle it, I worry I won't be able to. I worry I will start to feel really jealous again, or the issues I have with her other girlfriend will really push us apart, and I worry because I over-compensate sometimes for how I treated her in the past and that puts pressure on me.

Lately we've been spending more time together, though, and every time we get close again it's just like two falling stars: we crash into each other. Our feelings come back to the forefront and we start realizing how much we missed one another. I think that the inevitable conclusion is that we will come back together again. The question is just when, and she is waiting on me to make the move, since she has been ready.

I was talking to our mutual boyfriend and he was telling me she says she misses me and wants to spend more time with me and "wants me back." I want those things too, but I'm just worried. He says that I should ask her on a date sometime. I'm just not sure how to proceed. I'm not sure if I should. I want to, so badly, but things need to be right. I need to be right, and she needs to be right. So how do I know, and what should I do?

Re: How to make it work this time- And how to ask her out again