A/n: So this is my first time writing OUAT Fanfiction. My gf got me started on the show a couple weeks ago because she's been borderline obsessed with it since its inception (sorry darling) and now I'm possibly just as involved as she is. I'm quite nervous about offering this to the SwanQueen fandom cuz it's possibly the strongest and most talented fandom ever! So please bear with my novice attempt at writing. Thank you to my love, my darling, my beta Iwantafarnsworth, this one's for you my sweet. Do enjoy :)

The first time it happened they were having breakfast. He was having a stack of Granny's infamous pancakes together with a hot cocoa, with cinnamon of course. Hook and Emma were at the counter having coffee while he and his mom were sitting at the booth by the window. Hook kept leaning closer and closer to Emma as their conversation progressed, clearly flirting with his incorrigible pirate charm. But that's not what caught Henry's attention. Ruby was on the other side of the counter, opposite Emma and Hook, dressed in another of her stylishly short red skirts that showed off her endless legs. Her smile was radiant as ever this morning, one of his favourite things about her. It was hard to miss the look in his mother's eyes as she looked fondly in Ruby's direction. A mixture of interest, affection and what might be possibly jealousy swimming in those deep brown orbs. He smiled at his mom, knowing that she was oblivious to the fact that he was observing her. After all that his mom had been through, she deserved some happiness, someone to make her smile, someone to love her, someone to be hers. Emma already had Hook and his dad. But his mom had never shown any kind of interest in anyone. That is, until now. If his mom liked Ruby, then he was going to make every effort to make that happen. He didn't care that Ruby was not a guy. She was kind, sweet, funny and had the biggest heart ever. Plus, she was also a werewolf. What could possibly be cooler than THAT? Operation Wolf, that's what he would call it.

Henry sat in his room later that day trying to devise a plan to get his mom and Ruby together. Their interactions had never been much; only brief moments at the diner when she would take their order or his mom would complain about the overpriced lasagna. Aside from that, there was nothing he could really work with. He drew up a table on a blank piece of paper and tried to write down things his mom liked to do in one column and things he knew about Ruby's hobbies in the other column. After about an hour of intense thinking, chewing on the end of his pencil and staring at that spot on the far wall, he looked down at his table, disappointed by it's scanty fill. There were only a few things on Ruby's side as he really didn't know much about what the wolf did outside of the diner. His mom's list was even shorter as there were precious few things in this world that she actually enjoyed. He let out a frustrated sigh. This was going to be harder than he thought.

The next time he noticed it was two days later. He was walking down by the docks with Emma and Ruby, trying to gather information about the girl. He was glad when Ruby had said her shift was over and that she was going for a walk. He had been at the diner with Emma and jumped at the opportunity to get to know the pretty waitress better. He listened carefully to their conversation, enjoying the way Ruby's voice sounded. As if luck were on his side, he spotted his other mom walking on the other side of the dock and pulled Emma and Ruby along to go meet her. That's when he saw the look in his mom's eyes again. That affectionate longing mixed with a bit of turmoil. He couldn't imagine the war waging in his mother's heart. After all, Ruby was Red, Snow White's best friend. And Snow White was the Evil Queen's sworn enemy. She was probably worried that Ruby would not like her back because of their past enmity. But here now, they were just Ruby and Regina. It would be up to him to find a way to make Ruby see her as more than just the Evil Queen. To change that look in his mom's eyes from one of pain and loneliness to one of love and acceptance.

All through dinner that night he couldn't stop thinking about ways to make his mom look good. Situations where she could get a chance to be the hero. Sure there had been many instances over the last couple of years when his mom's trustworthiness had been more than questionable but there had also been those times when she had been the one to save the day, to save them all. Surely Ruby couldn't have forgotten that so soon. Either way, he couldn't exactly create another life and death situation for his mom to rescue the town. There had to be another way.

"Henry? Is everything alright?" His mom's voice broke through his thoughts.

"I'm sorry, what mom?"

"I was asking how was your day today, but you seemed lost to the world for a moment there. Is everything ok?" She asked, kindness and concern reflected in her brown eyes. He loved the way his mom looked at him. She could be at the brink of bringing down the world but the moment her attention turned to him everything else would be wiped aside and all he would see was the love she had for him.

"I had a nice time with mom. We had a late lunch at Granny's and then went for that walk on the docks with Ruby," he replied, pausing for a moment, "Ruby is really nice, I like spending time with her," he added in, trying to let his mom know that he was ok with her having feelings for Ruby.

His mom's forehead crinkled a little as she regarded him with what looked like a bit of surprise, possibly wondering why he had said that. He didn't mind that she might suspect that he knew about her interest in the waitress, what mattered was that now she knew that he would be ok with it.

The next day Henry was sitting on the swing at the park staring out at the playground but not really seeing anything as his mind was again racing trying to find solutions to the dilemma at hand. He could maybe take his mom's phone and send Ruby a text inviting her on a date. He pondered on that briefly before shaking his head, dismissing it. That would be too forward. Plus, if Ruby refused then his mom would be humiliated. His brow furrowed into a thin line again as he thought hard at the dirt on the ground. Maybe he could ask Robin to take his mom on a date at Granny's while Ruby is there. If the waitress saw his mom showing interest in someone else maybe that would make her feel jealous and realize that she had feelings for his mom. Again he dismissed the idea from his head. He knew Robin actually liked his mom. He didn't want the poor man to be led on by his antics. He huffed out a dejected sigh, not noticing Emma quietly seating herself in the swing next to his.

"That clump of dirt bothering you there, kid?"

"Huh? what?" he looked up, startled.

"I dunno, you were staring at the ground so intently like that clump of dirt just stole your dog or something. You alright kiddo?" Emma asked, not unlike his mom's concerned question the night before. He thought for a moment whether he should tell Emma what was on his mind or not. She was his mom after all, maybe he could tell her some of it and see how she responds.

"Sooo…" he began, "I have this friend…." he paused.

"A friend, huh?" she encouraged him on.

"Yeah, this, uh, friend, likes another of my friends. Like, like, like." he continued cautiously, pausing again to glance at her. She nodded, urging him on.

"My friend doesn't know if the other friend sees him that way but I know they'd be good together, I just need to know what the other friend thinks, so I can help my friend win her over," he finished, quite proud that he had avoided telling her all the details but still got the gist of the problem across.

His mom opened and closed her mouth, her expression like a deer caught in headlights. She blinked and looked away briefly before settling her eyes on him again. She cleared her throat before beginning to talk again.

"Um, did Regina by chance give you the talk as yet?" she asked tentatively. He was confused. What talk was she referring to? How did she know he was talking about his mom? He ran through what he had said to her in his mind, checking to see if he had unintentionally hinted to her that it was Regina he had been referring to. Nope, his explanation was airtight. There was no way she could have known. He looked up at her questioningly, "what talk?" He asked, emphasizing the word talk.

"You know, the talk. About liking girls and stuff like that," she responded, clearly out of her element here. His brow creased further as he regarded her before his eyes widened in realization. She thought he liked a girl! She thought his problem was related to himself!

"Mom no, this is not about me, it's about my friend. Honest!"

"Right, a friend. It's okay Henry, you're growing up. It's normal to start liking girls."

"No mom I promise, it's really not about me."

"Come on kiddo, it's nothing to be embarrassed about." she moved to pull his swing close to hers to give him a hug but he jumped off it to face her. "I think my mom has a crush on Ruby and I want to find a way to get them together!" He rattled out clasping his hands over his mouth as the last bit escaped his lips, not believing that he had just blurted everything out like that. He looked up at his mom, seeing a mixture of something he couldn't quite understand swirl through her eyes briefly before being quickly replaced with one of interest and a quirk of her eyebrow.

"Your mom and Red, huh?" she asked, something different in her voice. Henry was worried. What did that look and the sound in her voice mean? Was she homophobic? Did the thought of his mom liking another woman repel his biological mother? Emma's voice brought him out of his troubled thoughts.

"I think it's cool that your mom likes Ruby. It's about time she showed interest in someone in this place. How do you plan on getting them together?" she asked.

Henry looked up at her and smiled, his previous worries washed away by her words.

"I dunno. I've been trying to think of ways but nothing seems like the right plan. At first I thought of texting Ruby with my mom's phone but that's too risky and would embarrass my mom into going into hiding again. Then I was thinking of having Robin take her out on a date at Granny's just to make Ruby jealous, but Robin actually likes my mom so that wouldn't work very well. I need to get someone who has no feelings like that for my mom to take her out so that Ruby can realize her feelings for her." he explained.

"I guess that could work, but how do you know that Ruby has feelings for her? And besides, who do you know that doesn't have feelings for your mom and who she would agree on going on a date with?" Emma asked, looking across at him as he sat back on his swing. He pondered on it for a bit, mentally running through all the possible eligible bachelors in Storybrooke in his mind. He remained silently thinking for a bit before an idea so brilliant struck him, he almost fell backwards off the swing as he rushed to stand up again and face Emma.

"I got it!" he exclaimed, grinning at her.

"Okay, what is it?" she asked, eyeing him suspiciously. He silently looked at her, not sure how to say it, a silly grin still plastered on his face and a mischievous glint in his eyes. He could see Emma trying to figure out what he was thinking when her eyes widened. She had figured it out.

"No. no way, kid. Not happening." she refused.

"Come onnnnnn, you're perfect. I can trust you AND you don't have feelings for my mom. Plus, you're a woman, so she might be more inclined to say yes. Come on, please? For me? I want to see my mom happy again." he pleaded, putting on his saddest begging face. He looked at her as she thought it over, not missing the glimmer of that strange look again crossing her face before she reluctantly agreed.

"Fine, only for you. What do I have to do?"

"Yes!" he exclaimed victoriously. "For now, not much, maybe have lunch with my mom when Ruby is there and flirt with her a little?" he suggested.

A/n Hope you enjoyed! Please share your thoughts, suggestions and comments! Thanks for reading!