This is a very touchy subject, right? I'm going to try and convey my thoughts very carefully here, so please try and be receptive.
(Context for this is for your bog-standard straight courting scenario--I do not feel qualified to comment on how courting for any other gender scenario works.)
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In an ideal world, everybody would communicate honestly and openly. You could sit down with a girl, and have a conversation like so:
"Hi, I think you're attractive and I enjoy your company. Would you be interested in pursuing a relationship, or if not, perhaps a shorter-term physical engagement?"
"Yes/No/Not interested."
This is, needless to say, not how 99.999% of the population works--as I, and I suspect others, have found to our dismay. Negotiating these sorts of things is not just a TCP ack sequence or something.
The fact is that even were roles reversed, that is just not what we would consider a compelling user experience. Expecting explicit handshaking for every step of the relationship cycle is something only emotional robots expect.
In an ideal world, the following things would be true:
1. People know what they want in a relationship.
2. People know how to convey what they want accurately to other people, especially in terms of arousal or courting.
3. People are free to signal availability or interest without repercussion, and accept rejection just as easily.
These three things are obviously far, far from the case.
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There are very much conflicting cultural mores about how courtship is supposed to work.
On the one hand, we have hundreds and thousands of years of precedent (and perhaps biology, though I personally hope this is not the case) suggesting that the man is the one to initiate actions, and that the woman, if disinterested, will make her rejection known. Strictly speaking, we've got a bit more barbarous history behind us than that, but let's assume decent folk here to keep life simple.
On the other hand, we've got this recent push for more explicit confirmation for consent and for the more equitable distribution of first-move-making between the man and the woman.
These two things do not go together, and even worse, trying to come to a synthesis for your average inexperienced guy is a road which easily runs to ruin.
So, instead we find ourselves in this curious place where young men who mean well want to get with young women who also mean well. Unfortunately, the women are brought up expecting that the men will do the work, initiate everything, and the men are increasingly told that hey need to--to be safe and respectful, mind you!--wait for explicit confirmation of every step.
In programming terms, we are setting up for a deadlock.
Perhaps even more troubling, the hilariously large impact of social networks and whatnot mean that gossip is worse than ever, and there is no room to make mistakes if you are one of these young men. Worse, media is constantly reinforcing some awful blend of these two mores, making both sides seek after a state of affairs that simply does not exist.
There's some more issues I've seen, but you get the gist.