I can kinda see Hook and Regina having a fling, but I suspect that they’ll have way, way too many trust issues to get very far. Neither likes people who double-cross them, and both have a strong propensity to double-cross others. And they’ve already done that to each other a couple of times–Hook sided with Cora against Regina after agreeing to help Regina, and Regina sided with Cora against Hook when he thought they were working together. The two of them are also very flirty people and the flirting between them has been very minimal in comparison to other people they’ve talked to…which is interesting.
Speaking purely as someone who does ship Hook and Regina, their guardedness about flirting with each other is one of the reasons I like it. This is just my personal take on the characters, but I’ve always had the feeling that because both characters are still devoted to their dead lovers that neither will actually let themselves get too flirty or open around someone who could actually touch their heart or get too close. Regina had her “whatever you want to call it” with Graham for years, but she made sure he didn’t have his heart so he couldn’t feel anything and neither would she. Her crushing his heart was all about hurt pride. Hook flirts with most people, but he does it in a very off-putting fashion, like flirting with both a mother and a daughter or saying something outright crude. As a result the women tend to just roll their eyes at him instead of going for it. It’s like a self-defense mechanism to keep emotional attachments out.
I find Hook and Regina’s interactions to be different from their interactions with their other potential romantic interests, and that’s one of the things I dig about the potential between them. Regina knows full out that Hook suffered the same loss of a true love that she did and even by the same means of death. They knowingly and unknowingly make comments that dance around the other’s heartbreak. I’d love to know how much Hook overheard of Regina’s farewell to Cora after he “killed” her. I don’t think he knows the details, but he might have heard enough to suspect something. They’re like a mirror to each other, and sensing that could certainly make them more guarded about revealing themselves. It’s safe to flirt with someone else, but there are some people who, if you go there, can only be a real connection. That’s how I view these two.
So far everyone’s betrayed Hook, and Hook’s betrayed everyone. There is no Hook ship that doesn’t have that element to contend with, unless you count Ariel who doesn’t actually exist in the Once-verse. Interestingly, Hook and Regina keep forming alliances despite the betrayals.
My suspicion about Regina betraying Hook this time is:
She tells him her plan about leaving SB with Hook and Henry, and she explains that there is some kind of mechanism in the curse that will destroy the town if she leaves. That means his crocodile will be destroyed with everyone else left behind. Henry calling her a villain might give Regina pause though, and she decides to back out of the plan…. thus she would have betrayed Hook by doing the right thing for once.
The show could go a totally different direction with it, and I can’t wait to find out what they decide to do. I just really find this dynamic to be complex, intriguing, and understated so far.