I agree, he should make that clear to her, up front. There are fewer boundaries/less potential for paralysis up front because you don't know the person well enough to have any/there isn't a relationship/friendship. If you take two years to get to know someone (as he described) and perceive that they are giving you signals of interest, you've got more at stake at that point than being perceived as a pig; you have a relationship with that person that you will likely lose if she responds with "no." In the simplest terms I think his biggest problem is getting to know the person, too well before approaching them as a potential mate. The "male friend" turned someone trying to breathe in your ear and lick you is almost never flattering. It's worse than the lusty groping pig man. He's apparently experienced this response, but he hasn't learned it because he's not just out for sex. ---that's not the root of his problem. He might not even be a nice guy.
Totally. This is why I put "nice" in quotes - I don't think these are nice guys, I think they're just guys who lack backbone and mistake passiveness for being nice. In their eyes they're nice, and they're often mistaken as nice because they're not forward with their interests - but in the end, this puts stress on them and the people they're around as their underlying motives come to the surface.
Anyone who has that much self control is not spineless (like any investor on the floor who didn't sell sell sell last week). He might not be "nice" either and I wouldn't call him passive. It does come back to his underlying motive which seems to me to be not only getting what he wants. As I see it, he's trying to please and predict another person's actions/responses (and he's taken the time to get to know them well enough to think he's figured out both) without disclosing how he feels or what he's really after/what he wants. That's calculating. Anyone who calculates that much before acting is very difficult to handle.
The people I'm talking about are very much spineless, without question. They may also be calculating, but if they are they're not successful at it. And if they really understood people they'd realize that a more direct approach would be more successful. I'm not just making up some archtype here; I'm relaying the experiences of myself and dozens of men I've talked to (many who have shared their own experiences with this in other comments).
There are people who are very self-disciplined and calculating, who control their feelings and slowly create experiences that try to control the outcome they desire. That's not the type of personality we're talking about here.