How long should you wait?

Making the assumption that he also appears to be looking for more than a first date...what’s wrong with sounding up front?

Confidence is attractive (but conceit isn’t) and I would think a woman who knows what she wants and says it, would be attractive too. Unless it’s not what he wants, but if that's the case, why waste his time or yours?

Decorum dear... At least 5 minutes... Don't want to appear to be in a rush ;)

Wait until you feel comfortable saying it. If you feel uncomfortable, there is probably a reason why, which could be a red flag.

I think it depends on the individual guy, was he a perfect gentleman, or a lecherous slob?

I think this could be discussed on the first date. If not, and if there is to be a second date, discuss it then. No sense wasting each other's time.

It depends on many factors, but trust your instinct. There is no general social convention.

Make a second date and show up in a wedding dress. That should give you an answer. ;)

Depends on what youre looking for

That's really hard to say because it is such an individual thing.

Personally, 15 years ago I'd probably be scared if someone was too upfront. Now I'm at a point where I'd just prefer people to be straightforward right away; wanna discuss the big supposed taboo questions on the first date? Go for it.

Point being that I think it is impossible to give a proper answer here because it depends so much on the personality of the other person and at what point in life they are.

Definitely immediately

What do you mean?