Having a plan of action is a little tricky when they're still flying blind. He's joking, but he's not joking, but he doesn't want to imply that he's making any assumptions about what she'll be ready for when. On the other hand, he decidedly is interested in starting something. It just feels like a fine line between showing her exactly how interested he is, and pressing the issue. The latter is something he 's dead set on avoiding.

But.

He matches her sidelong glance and shrugs very slightly, glancing out over the water in a casual fashion, before he stops rubbing her neck to run his fingers slowly down and then back up her back.

There ought to be something about hook, line, and sinker said, but maybe it's too easy.