Leading Lady

At what point is a woman leading the man on? (And for my own sanity, I'm taking this back to the "girl" "guy" level.) Instead of talking around this, I'm just going to put it all out there.
So NotRoger and I have a long history. And it's not just of the relationship kind. I've known him for 5 years and we've been friends for about 3 of those years (the rest of the time being when he was too immature or when we fell out of contact for awhile). In the beginning he was someone who I wanted to like me because he was a challange. My way of doing this was to "be in his presence" whenever possible which led to some very funny stories (a later, more comical blog perhaps) and to share the same interests (see NotMiranda's blog about weaving that web). I'm not sure how he felt about me back then and all I can use as evidence is the following:
1) When asked if I was his type, he said, "Yes and no, but more yes"
2) One time when he passed out while drunk, he fell asleep holding onto my leg
3) Whenever I was my usual "tease" self, he seemed very interested

Ok I know that is very weak evidence but remember what I said about him being immature for awhile.

Fast forward to a party at a friends house when I was living out of the area where we had met but was in town for that night. As everyone was leaving the party I used one of my patented moves/items: Lipgloss. I can't reveal any details of said "move" but things started moving in the direction I wanted. After the fact, I learned that while I was in the bathroom he told my friend he wasn't sure if I wanted to kiss him. She assured him I did (thank goodness), vacated the room and we proceeded to makeout...a lot.

Basically, after that night we hung out some more (we were then living in the same area) but things were sort of weird as I didn't know his intentions or even my own at the time so it never went past making out at his house after hanging out watching a movie or something.

Then he moved which began about 8 or so months of us not talking until one night when we talked online and he ended up finding me on some internet friend site or something and saying how pretty I was and that he wanted to hang out again.

I of course was suspicious and gave many excuses as to why I couldn't. In the back of my mind though, I knew I wanted to see him and was happy to have the opportunity at an upcoming party. Unfortunately, he had other plans (drinking) and was not coherant enough to understand when I whispered in his ear, "lets go outside." He was coherant a few days later when I told him I was sad he hadn't been into me that and to make this very long story a little shorter this takes us up to a few months ago when we escaped any chance we got at parties and I went to his house a few times.

Now, back to my original question: At what point is the girl leading the guy on?

I have so far not said anything to lead him on or make him believe this is all something more than it really is. However, I have also NOT said a lot. I don't tell him about going out on the weekends to find hot guys or about a certain one I'd really like to have something more with. When he starts to divulge actual feelings I tend to cut him off or change the subject before it's my turn. I've also given the excuse, "I don't talk about things like that."

I wish I knew the answer to my own question but I don't and while I have an amazing gift of being able to rationalize ANYTHING, I'm starting to feel bad about it. But should I?