Perspectives

So my roommate was hooking up with this guy, and then he told her there was no future so she got over it and started hooking up with his best friend (the next day). Which I mean, it's more complicated and somewhat justifiable but still not a good situation to find oneself in. Anyway the first guy confronts me about the situation and asks where she is and gives me his take on things. He said something along the lines of:

She always contacted me first; she always text me to go places. I deducted from that that she wanted a relationship, and I didn't want to lead her on, so I told her up front that I wasn't interested past the occasional weekend hook up. 

I started thinking about his newfound revelation, that maybe guys overanalyze just as much as girls do. My problem is that I like his roommate. I don't know if I'm ready for a relationship or anything, given my track record. But I could definitely see this thing going somewhere. But he's really shy. So I have to text him a lot of the time, and when we hang out he gets more comfortable and outgoing and we have a lot of fun. But am I not supposed to contact him? Is his roommate going to over analyze this situation and tell him to run? 


When it comes to shamelessly flirting with no intention of getting serious, is it okay to take charge?