you're 100% right on cloud being able to do something about his apparent "dislike" of being around jessie, but he does absolutely nothing. it's what i talked about in my analysis. cloud grunted and pouted but when jessie asked him to lay off of barret for a little while, but he still listened when he had no real reason to. that's why i'm 100% certain he was showing off for her. we also have to put into perspective of camera angles of the bike chase, and there was that shot when jessie wrapped her hands all around his waist. as you pointed out, there's many points when cloud could stop jessie if it was too much, but he didn't even grunt out a single word. obviously the wrapping around his waist is supposed to mean something, and that point is that he's most likely just as enjoying it as she is

but as you said, he doesn't know how to deal with the forwardness so finds it easier to use the facade. but in the end even that backfires on him since his walls are weak around her, as she was the one who started to bring them down.
and as for the hug, that's what i thought as well! and did you see how his hand lingered on her arm before using the cool facade to drop it and look away when she asked about the date? and even though we have a choice to her question, it's canon that he agreed (and was perhaps thinking about it the whole day, even when he was with aerith) since he brought it up at the pillar, before
she did at that.
i'm going to finish the game today, so fingers crossed on the ending. can't wait to see ?
OH YEAH and some trivia: cloud begins to care about everyone and is concerned about their well-being near the end of the game, constantly asking everyone in trouble if they're okay. but in the very beginning of the game when he didn't much care for anyone, jessie is the first person he asks that to. it possibly means nothing but it's just something that suddenly came to my head last night.