Chapter two

-Two days later-

"I think I may have made things worse…" Henry sighed, falling onto the couch that Emma had convinced the pirate to bring into his quarters on his ship.

Hook sat down next to him and raised one of his eyebrows in his signature move.

"And why is that, lad?"

"Ma left earlier than she usually does after dinner and I don't think that they had spoken to each other since…I think that I might have freaked her out a little. Maybe we came on too strong?"

Killian just shook his head and replied, "coming on strong may be the only option considering that you are trying to match together the two stubbornest women in town."

The younger of the pair sighed heavily, falling back against the couch, he lolled his head to the side and asked, "so how do we step it up? I mean, there was so many things that could be keeping them apart. How are we supposed to show them that none of them should matter?"

"We're just going to have work through each issue and hope that they will eventually work it out for themselves. It would be unreasonable for us to deal with everything for them, so we just need to pick the biggest issues first…"

Henry nodded his agreement and thought for a moment. He couldn't wait for a time when all of the barriers between his mothers wouldn't matter anymore, because they would be together and so in love that they wouldn't even think about what had been keeping them apart. But the fact remained that there were many issues in their way. For starters, there was the fact that Regina had devoted a lot of time to trying to make Emma's parents miserable, Regina was technically about sixty-years-old and she had cast the curse that had left Emma as an orphan for the first twenty-eight-years of her life. Both women were extremely insecure about love after everything they had been through in their lives and Henry could hardly blame them for being cautious. But it was seriously beginning to ignore him the longer they were just friends. He could tell that they both liked each other very much and he had to find a way to make sure that they could see that too. He was getting sick of them claiming they were friends when they already basically acted as though they were married.

"What should we go for first?" the boy sighed as it occurred to him just how many things were keeping them apart.

Killian shrugged and replied, "perhaps the most obvious issue is that of Snow and Charming…"

Henry frowned for a moment and said, "but they've accepted mom…they treat her like one of the heroes…"

"Treating the woman who made their lives miserable for decades as an ally is one thing, but accepting her as their daughter's girlfriend is another thing entirely. We need to figure out just how they would react to the news. I believe that this would certainly be something that both of your mothers would be worrying about. Emma hasn't had parents for long and she probably doesn't want to do anything that could put their relationship at risk and Regina wouldn't want to take a part in tearing them apart again."

The brunette nodded slowly, he hadn't really considered just how his grandparents would feel if Emma and Regina were to get together. He could imagine that they would probably be shocked at first since they were usually the last people to notice what everyone in town already knew. But he also had no doubt that they wanted nothing more than for Emma to be happy and that a relationship with Regina would be the saviour's happy ending. Therefore, they should have no real objection to the relationship. Of course, that all very much hinged on how much they truly believed in Regina. It was very possible even though appeared as though they were friends with her, the pair of them held ill feelings towards her for what happened in the past. They did have every right to do so, though, which meant that Henry could only hope that they wouldn't be the thing that made his operation completely fail.

"Do you think that they would be against it?" he asked sheepishly, hoping that everything his mind had just worked through was not true.

Killian shrugged again before he replied, "I don't pretend to know the inner thoughts of the Charmings, lad. But anyone can get used to something given time, so maybe giving them some kind of warning as to what could be coming would make their potential reaction less…hurtful?"

Henry thought about this for a moment, thinking about how that conversation would go. He had long ago noticed that Snow usually didn't react well, so he decided that it would be best to allow his grandfather to break the news to his wife so that she would have time to react to it in private.

"I guess I could do that…but how would that get back to my moms?"

"Your grandparents do enjoy making their feelings known, so I'm sure that one of them will blurt it out to Emma once they figure out just how they feel about the prospect of her being with Regina."

"And if they can't deal with it?"

"Then I'm afraid that our operation may have already failed," the pirate sighed.

Henry tapped his fingers on the counter as he continued to look at the diner door.

He was more than grateful that David had agreed to have lunch with him the very same day as his conversation with Hook, since he couldn't imagine that he would be able to handle worrying about his reaction for long. Killian had dropped him off at the diner and had asked Ruby to watch him while he waited for his grandfather. It had been exactly five minutes and he could already feel his anxiety building as he wondered how he could possibly start the conversation.

Before he could think more about this, though, the bell over the door rang out. He swallowed hard, but the tension quickly fell away when he saw that it wasn't the person he had been waiting for.

The boy offered the blonde woman a small smile as she approached the counter, which she returned.

"Hey Kathryn," Henry said, turning around so that he was no longer facing the door.

"Hello Henry," the woman returned, before motioning to Ruby, silently asking for her usual order of coffee, which the brunette set to work making. "Are you alone?"

The boy shook his head, "I waiting for David to come and have lunch…"

"So why do you look so nervous?" she asked with a furrowed brow, "surely you've had lunch with your grandfather before…"

The brunette bit the inside of his cheek and internally berated himself for being so obvious, before he replied, "I just have something important to ask him and I don't know how he's going to react."

"Is this for your operation?"

Henry opened his mouth to say something, before her words finally registered and his eyes widened, "w-what operation?"

The blonde laughed and shook her head, replying more quietly this time, "your mother told me what happened at dinner the other night and I can only assume that you're planning something. I'm fairly certain that you already knew what bi-sexual means, Henry, so obviously you wanted your mother to admit something in front of Emma."

"My mom told you what happened?" he asked with a furrowed brow.

"She tells me everything that happens between her and Emma."

"Really?" Henry blanched.

Before Kathryn could say anything, she heard the clicking of heels, which meant that her coffee was ready and looked up to Ruby with a smile.

"Thank you," she said, accepting the beverage and placing a few notes on the counter.

Ruby nodded and took the money, walking off to put it in the till.

"Women tend to want to talk to their friends about their crushes," she whispered by way of reply to Henry's question, before she turned on her heels. Henry was about to say something, but she quickly added, "I really should get back to work, but do let me know if there is any way that I can help. I really am sick of being poofed to the mansion."

The brunette boy furrowed his brow at the last part, but she was already walking away before he could question it. He blew out a breath of relief as he realised that Kathryn had just confirmed one of the things he had been most worried about, his mother definitely did like Emma and somehow it was comforting to hear that the usually composed mayor poofed her friend into her home to rant about how she felt for the sheriff. He smiled slightly when he thought that the former queen would be frustrated at the ever-childish woman in a different way when the two of them finally got together.

Before he could think any more on this, he looked back up to the door and smirked slightly as he saw David awkwardly say 'hello' to Kathryn on the way out.

After a few seconds, the prince approached the counter and smiled at his grandson and they silently agreed to go over to the booth that they usually sat in.

"Thanks Rubes," David said after she placed menus in front of them, "but I think that we'll both just have our usual's."

The waitress just rolled her eyes and reached down to collect back what she had just put on the table, "I honestly don't know why Granny bothers having the menus printed, everyone just orders the same thing every single day…"

Henry and David smirked at her mini rant as she walked back over to the table and the older of the pair looked back over to his grandson, "did something happen?"

"I think she was late to work because she wanted to spend more time with Belle and Granny yelled at her."

The blonde laughed lightly, knowing full well that Granny and Ruby would probably make up later once the diner was no longer busy. Once his amusement fell away, he remembered what that Henry had sounded somewhat worried on the phone when he had invited him to lunch, which was why he had rushed over to the diner as quickly as possible. He honestly had no idea what his grandson could possibly want. Everything seemed to be going pretty amazingly well recently. They hadn't had any crises since Belle had sent Mr Gold over town line. Everything had been unusually peaceful, so he was rather anxious if Henry knew something that could end Storybrooke's current tranquillity.

"So…" the deputy began, looking over to the boy expectantly.

Henry swallowed hard as he was reminded that there was a reason that he was here other than having lunch with David and he noticed just how worried the man looked.

"I just wanted to ask how you would feel about something…I would like to think that you would be okay with it…but if you and Snow aren't, then it could ruin everything…so I really hope that you'll be okay with it…"

Charming held up his hand to silence the brunette, who quickly clamped his mouth shut and looked at the man apologetically, knowing instantly that he had probably just confused him further.

"Unless you tell me what it is, Hen, then I can't tell you if I would be okay with it."

Henry took a deep breath and nodded, before he said, "I really don't know how to say this…so I'll just come right out and ask. How would you feel if my moms got together?"

The blond opened his mouth, allowing it to hang open for a moment, before he quickly closed it. This was certainly not what he had expected, but it wasn't the concept that he was shocked by, it was more that his grandson also knew about the possibility.

"You've noticed that too?" he finally asked after a few seconds of silence.

The boy blinked a few times as he worked through each word of the man's reply, trying to figure out if there was something he was missing.

"You know…" Henry sighed, finally realising exactly what he meant.

"I've known since Neverland…it was pretty difficult to miss, but I still needed time to come to terms with it…"

"And you've had enough time?" the boy asked timidly, hoping beyond hope that he wasn't about to be told that he would object wholeheartedly to their relationship.

"It's hard to deny just how perfect they are for each other; I've been okay with it for a long time. Which is why I've been quite shocked that they haven't gotten together yet and I haven't had to tell Snow that I've known for so long…"

Henry smiled at the news, before his smile feel into a frown and he asked, "grandma doesn't know?"

Charming laughed lightly and shook his head reassuringly, "she certainly didn't figure it out when I did, but she has known for quite sometime. During the missing year, it was obvious that it wasn't just you that Regina missed. Snow ranted at me for hours over it and I spent hours trying to convince her that it would all be fine and that we should give our blessing if they ever had a relationship. It took a while, but she eventually agreed and we have been waiting for something to happen, so that we could reassure them that we would be okay with it. But then Regina got together with Robin and Emma with Hook for a while…I thought maybe we were wrong…"

"But you know you're not, right? They belong together and I don't get why they're just pretending to be friends when they know that they can be so happy together…"

"Love is not logical, Henry, though it may seem as though it is to onlookers. We might not understand what is keeping them apart, but we have to respect that they need time to work through whatever it is…of course, I'm sure they have had more than enough time…perhaps one of your operations is in order?"

Henry smirked at his answer, instantly relieved at what he had been told and nodded, "it's already in the works…."

Charming chuckled lightly and asked, "and what is it that Snow and I can do to help?"

"Maybe find a way to casually tell Emma that you would be okay with her being with my mom?"

"Casual isn't exactly our speciality…" David frowned, trying to remember the last time that he and his wife had been subtle.

"Could you try?"

"I suppose…but there is a chance that Emma will find out about your operation…" he replied.

Henry shrugged and said, "it's okay, she already knows. Maybe you and grandma can convince her that she should actually help make it work…"

A/N Reviews would be much appreciated XD