Did you tell him that the red marks on your neck were where the pool boy was sucking on it? And that he pulled your hair a little too? hehe. Sorry.
I think that as long as your DD is taken care of, and you mentioned that you already discussed the trip with him thats enough! But, I do see what your saying. Maybe you should wait until you are already gone to tell him, "oh, by the way"...
I also agree that he probably was trying to reach out to you, but until he is proving himself trustworthy he doesnt deserve for you to notice! I also agree that you should wait to talk to him about the posibility of his job interview. And your right, it does show him that you arent sitting wondering what hes up to!
I guess I gave the wrong finger to the wrong man...