Of course a lady should make the first move, if she is so inclined to do so. A little old fashioned seduction is not only appropriate, but will be appreciated. If he is doing the "dual entendre" thing, he is signalling anyway. And if you are concerned with rejection, please put it out of your mind. Get out the Martin, sing him a song, and just create an enjoyable atmosphere. The rest will come. If it doesn't, then this bozo is thick and not worth much more time. But as you describe this, I would assure you that the result will be what you want, m'dear. Just be sure of what you want.

Good luck,

Mick