Hook is an interesting character in that his self confidence seems to come in ebbs and flows. Sometimes he’s ridiculously cocky – and the viewer can easily see he’s covering up being self-conscious and maybe a little out of his element. But when it comes to love, unlike many, Hook/Killian is extremely confident – not because he feels whoever is on the receiving end should be grateful, or owes him something for his love. And I don’t think it’s because he knows that person will ‘come around’ – it’s because he’s going to love that person irregardless of whether they return that love. Because he knows he is a better person for loving them, regardless of whether or not that love is returned.
I want to add, that I think Hook is already seeing that Emma has feeings for him, they’ve been quite friendly so far (rum, coconuts, kisses) so as you said it’s not a matter of her ‘coming around’ to his way of thinking, b/c I think she’s already there (or at least an inkling of a feeling) and she will admit it one day when he is worthy of her love. As he said he won’t need tricks, b/c he hasn’t already and she’s starting to fall. Even Regina called her out on it ‘you think it’s the best plan b/c your boyfriend came up with it’ And that was before the kiss, so Emma’s obviously been showing some affection to Hook if others are seeing it.
If one is to engage with the primordial forces of darkness, one must expect a little social awkwardness