Three months is an impossible amount of time to wait. If I was seeing a girl 4 times a week for 12 weeks, and for some reason progressing into sex didn’t feel right it would probably mean that it’s not going to happen, it could be that I’ve at last found my long lost sister who was abducted by roaming gypsies at birth, but love-of-my-life-until-death-do-us-part material, she is not . As matter of fact, yes, it would feel awkward, and if I feel we could be unto something but sex feels uncanny, I would start conjuring up all kinds of probable psychopathology going on in the background.
Ok. Switching into brother/dude-friend- mode. Date #6 or W2 does sound like a safe amount of time to wait but in a way it’s got to do more with the guy’s attitude. What and how he does it. How much time, energy and money he invests in it (i.e. getting you into bed). I’ve really given up on trying to guess at how you know you’ve got a keeper but I do know my attitude as a guy is different when I see some kind of relationship potential in it, as a matter of fact, I don’t even expect to “land a try”” on the first dates, I want her to see who I am in a more complex way before the sudden intimacy sex brings about, and yeah, I want to see who she is before I’m sex crazed and trying to get her clothes off every time we’re alone.
But. But, but, but, there’s another dimensionality that makes it more complex, it’s not only “when” but also “what” you do on those first trysts. There’s things I’ll try to get away with on some women that I’d never even consider with another, and it all depends on where I see it going. As matter of fact, there was this one girl with whom we were being very romantic/conventional through out and carrying on well enough until about six months into it we accidentally discovered a level of kinkiness/intensity we had been both trying to hold back thinking it was inappropriate and might scare the other away.
Lastly, no need to protect the fragile male ego, men who use their insecurity to get a grappling hook on you have mother issues they should figure out in therapy, sooner or later you just learn to deal with rejection, it’s just part of it.