Timing

When is a good time to try to break the ice? I don't want to rush but inaction leads to nothing. And if I wait to long will I seem like a creep? Before approaching a lady of interest.

Break the ice as soon as possible. Chances are she might have feelings for you too. Just don't rush the relationship part.

Yeah, I'll try not to over think this to much ,any suggestions on some topics I should stay away from,I'm not to social with new people,so my conversation skills are very unpolished

You should use your environment to your advantage. You can also use what she's wearing to start a conversation (just don't say anything pervy). If she's wearing a shirt with a picture or something on it, you can use that.

It's like this you always break the ice to early for the relationship, but first off, you need to establish CHEMISTRY if you just instantly going up before realizing youre compatiable, youre gonna have a bad time, first establish CHEMISTRY/Repore with them, but if you break the ice to late, you'll get bad results, AKA friends only. you'll miss the limited mark of openness. so the second you notice th chemistry, go for it

Huh... People who are single giving advice on how not to be single. A bit ironic, don't you think? Would you go to a blind person and ask how to see?

But... the question is why are they single? They have just gotten out of a relationship, or choose to be single... There are plenty of people who are also very good matchmakers and facilitators. Like they can set people up with each other, provide insight and advice, etc. And yet they themselves have never been in a relationship. How to see, that sentence did make me lol though, not gonna lie!

Sun, And this time it's not because of you?! *gasp* Izumi, I know, I just find it a little funny. I more than understand how it's actually kind of hard for a good chunk of people to not act a little like a fool when seeking a mate. But, there is no such thing as "timing". It's not a universal thing, anyways. All you can do is be open and mature about what it is that you want. Don't go for a friendship and be disappointed when it doesn't become a relationship. Also, just remember that people are people, no matter the sex. Just casually talk and try not to over think things. I try to just go with the flow and so far, it's worked just fine for me.:)