Initiative

I've never been in a relationship where a woman shows enough iniative to talk about long term plans or make plans for us.

I know that there's no law that says a man can't iniate such talk, but if I do, I have concerns about bad timing or whatever.

So how long does a woman have to know a guy before she can start discussing plans with him(including him)?

As long as it takes.

I don't think you can put a time frame on it. Everyone is different, and has their own time frame for things. Each relationship develops differently, and at a different pace. You both have to feel comfortable enough with bringing up such topics. I would say that perhaps a general reference to committment toward partnership would be anywhere between 3-6 months. Committment to spend your future together could be anwhere between 6 months to however long you need.

I would also say, that if after this time, you see no progress toward future goals together at all, then maybe it's time to reassess, and see just where things are going, or not. Then perhaps decide whether or not you want to continue in that way with that person, or to move on.

I can't imagine that if a woman likes you, that she wouldn't be delighted to have you initiate such a conversation. Lots of women are convinced that men hate such conversations and immediately get turned off, so they hesitate to launch into it.

Timing ... I think conversations about exclusivity probably fall into a 3-6 month range and longer term stuff - maybe about a year? This is pinned to real-life time and seeing each other a few times a week.

If you're talking about long-distance or Internet relationships, then I think you need to think in a slightly longer time frame and keep the options open until you know how the two of you react after you've spent some intensive face time together, because it isn't always the same.

I'd just tell her that you'd like to spend a quiet evening together talking - lay in some yummy food and drink or find an intimate restaurant and then ..... talk.