This conversation takes place soon after the season five finale but assumes all the split Regina nonsense never happened.
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Regina: (she walks into the living room to find her son watching TV) Hey Henry, can I talk to you for a moment?
Henry: Sure. Am I in trouble? (He shuts the tv off and makes room for her on the couch)
Regina: No, I'm just a little concerned.
Henry: About what?
Regina: Well your mother just told me that she invited you to go sailing with her and Hook today but you told her you already had plans.
Henry: So?
Regina: So, all you've done today is sit around the house.
Henry: (looks down but doesn't respond)
Regina: As far as I know, this is the third time in the last few weeks that you have declined spending time with her. Is there something you want to tell me?
Henry: No?
Regina: Are you mad at Emma? Because she sounded a little upset that she hasn't really seen you lately.
Henry: (looking guilty) It's not her.
Regina: Than what's wrong?
Henry: If I tell you will you promise not to tell Ma?
Regina: (bites her lip in indecision) I don't like keeping things from her but if it means that much to you than yes I promise.
Henry: (lets out a deep breath) I hate Hook!
(The sudden outburst startles Regina)
Henry: I mean as I person I guess he's fine. I don't actually hate him. And he's always been nice to me personally.
Regina: But...? (she prompts)
Henry: But he's not good enough for Ma (He says deflating; wishing he could tell her who would be good enough.)
Regina: I agree (She says before she can stop herself. But really it's not like she's saying anything she hasn't already told Emma personally.)
Henry: (encouraged by her agreement he becomes more enthused about the conversation) I just hate being with them when they're together. I guess it would be weird to see any parent being lovey dovey in front of you but they make me seriously cringe. He's so...possessive. And she just looses all autonomy because she's like terrified he'll reject her again. And why wouldn't she be when he said all those horrible things to her when he was the Dark One. She was a Dark One also and she didn't seem to become a complete asshole. (Regina would normally scold him for his language but he continues before she can even get a word in.) And he doesn't understand like any references to the modern world. Come on dude you've been here for like three years, learn how to use a remote control already! He tries to bond with me but what can we even do besides go fishing if he won't learn anything about this world?! If he tried to throw a football with me he would probably end up popping the ball with his hook hand! And I don't think I want a parent-figure who has also slept with one of my grandparents, it's too weird. Plus I don't need a Dad figure anyway, I have Grandpa! And I know you're not Grandpa's biggest fan either but you have to admit he's a much better role model than a sleazy pirate. At least he has a job. Which is another crazy thing! How is he even surviving right now? Is she paying for everything? I know he probably has enough stolen merchandise on that ship to last a while but we don't exactly barter in Storybrooke and the only pawn shop is Gold's so I don't think he's sold any of it there. Even if it's gold on the ship, how did he trade the gold in for cash? I don't think Storybrooke Community Bank does that. You would know better than I would though. (he concedes)
(Meanwhile, Regina is stunned into silent-amusement during her son's rant but decides she needs to stop him as it looks like he could go on forever about this.)
Regina: Henry! (She practically shouts to get his attention.)
Henry: (takes another deep breath) Sorry.
Regina: It's okay just slow down. (she rubs his arm) So, you don't want your mother to be with Killian.
Henry: No
Regina: I thought you liked him? When did that change?
Henry: I never really liked him but he was alright. He helped when we were in Neverland which I appreciated but I always thought he was not good enough for Ma. And of course at first it was because I wanted her to be with Dad but then we went to New York and he was just some creepy werido who basically stalked her and never changed his clothes. Even when I realized who he was again I didn't think much of him but by then they were already dating. And she never really seemed too into him, you know? I thought it would be temporary but then things kept happening and she seemed to get more...dependent on him and now we're here.
Regina: (Regina understands the feeling. Her own past with the Captain is far more bitter. She did vaguely appreciate his help at times yet thought he would never become a permanent fixture in her life.) Why haven't you talked to Emma about this?
Henry: (shrugs) I feel bad.
Regina: Why?
Henry: Because she deserves to be happy and even though I think she's making a mistake, who am I to tell her who to love?
Regina: (pauses to think) That's very understanding of you Henry. However, you are very important to her. To both of us. I think she would want to know if you had concerns even if ultimately it didn't change anything.
Henry: You would have wanted me to tell you if I hadn't liked Robin? (he asked skeptically)
Regina: (she cringes at the memory of her dead boyfriend) If you had legitimate problems with him than yes. I care about your opinion, Henry.
Henry: Well I didn't think he was good enough either. Especially after putting you though all he did. BUT again, you claimed to be so happy so who was I to complain. I just want you guys to be happy.
(Regina hugs her son close and thinks through her response. It hurts to bring up the memory of Robin. Especially since Henry is now shedding him in a negative light. But maybe that's a good thing some times. She puts him on a pedestal in her mind because of the way it ended and tends to disregard all the heartache he put her through before that.)
Regina: Do you think that maybe no one will ever be good enough for your mothers? I know I'm probably going to feel that way about you.
Henry: Maybe, but...
Regina: But what? (she asks when it doesn't seem like he'll finish the thought)
Henry: Never mind
Regina: Come on. You've told me everything so far, uncensored I may add, you might as well tell me this.
Henry: (he heaves a great sigh. This conversation has really gotten away from him if he's about to admit this.) Maybe you're right and no one else is good enough for you two. However...I think you two are good enough for each other.
(It takes a moment for Regina to process what Henry means by this.)
Regina: ...Oh
Henry: (nods)
Regina: Please don't try to parent-trap us. (she finally responds trying to lighten up the sudden tension)
Henry: (laughs) I won't. (he promises) But it's not just because I want my parents together that I think this. In an objective third party point of view, it just makes logical sense. If I was writing a story this would be the obvious conclusion.
Regina: I guess I should be relieved you don't have that pen than. (she sasses feeling uncomfortable with the emotions her son is bringing up in her.)
Henry: (rolls his eyes at he comment.) I'm not the only one who thinks this.
Regina: Really? Who else? (She can't help her curiosity on the new subject.)
Henry: Lots of people. But it's all a moot point anyway. (He deflates again)
Regina: Moot point?
Henry: If she's with Hook. And you insist that you don't feel that way for her than it doesn't matter how perfect I think you would be. So yes, it's a moot point. Which is...fine. But I can't be around Mom and Hook too much or it makes me angry.
Regina: Okay well I still think you should talk to Emma about your concerns but if you really don't want to I can at least suggest to her that you two should do activities without the pirate.
Henry: Thanks Mom. (he squeezes her tight once more before standing up and heading out of the room.)
Regina: Henry? (she calls to him before he's fully out of the doorway.)
(He spins around and looks at her curiously)
Henry: Yeah?
Regina: You really think we'd be perfect?
Henry: (grins) Yeah, I really do.