Re. confessions of love/asking out/hints, etc: there are heaps of degrees of this stuff. This includes, but is not limited to:
1. Declaration of love (almost always, in the real world, a bad idea).
2. Declaration of like/crush
3. Bringing up like/crush during conversation ("Blugh I'm so ugly no one likes me!" "You kidding? I would go out with you in a heartbeat if I thought you'd want to!" [note: bad example, but you get the idea])
4. Asking out on a date.
5. Asking out to one-on-one activity not explicitly stated to be a date.
6. Hitting on.
7. Heavy flirting, including physical contact etc.
8. More subtle flirting.
9. Being extra-nice.
10. Treating 'em like anyone else and not doing anything at all.

Personally, as I mention, my preference is "subtle flirting", getting heavier, and eventually leading through the gradients to an explicit date (or, more likely, "we're a couple now! :D" ...I've never really "dated" much <.<).

So, to take this back to the original conversation: It's my understanding that Objection was talking about #1, possibly #2, which I think was generally determined to be a Bad Idea for the most part. Then we were discussing the differences in taste/intention/message between #4-5, and 6?-8. That is, while (in my opinion) declarations of love are almost always a bad idea, asking out and as I call it "organic development of a relationship" is purely down to personal preference, and unfortunately unless it's come up in conversation isn't really something you can know in advance.
As I explained before, the main reason I prefer "organic development" over being asked out is pressure. Asking me out requires an answer, which requires me to think about it, which I will over-do and puts stress on me and makes me feel awkward and blegh. It also, in my view, deprives me of the part I find most fun about a budding relationship: I like all the flirting and touching and uncertainty and stuff which is all bypassed by a simple "will you go out with me?"* The "organic" method also, I must confess, gives a measure of "plausible deniability" - it can be just some fun, and I can nip it in the bud before it goes too far without anything having actually been stated, "put out there" so to speak.
But, again, this is not advice. It's purely explanation of opinion.


*Side-note: it is my opinion that "will you go out with me?" or similar should be avoided wherever possible. A specific date, time and activity is much better.