Her first week back working at the diner, Ruby picks up a little quirk. She takes to writing little messages on people's to-go cups. Words of wisdom, small kindnesses, sometimes it's nothing more than a smiley face or a heart and a scribbled 'have a wonderful day.' People seem to like it. They smile at her, in a genuine sort of way, respond with kind words of their own, and then go about their business, and Ruby feels that much better for having brightened their day at least a little. It doesn't hurt that's it good for business too, but Ruby doesn't really care about that.

It's a way for her to give back, in a sense, and she enjoys it. There's a certain satisfaction she finds in it, especially when even the toughest of customers leaves with a smile. It's in that interest that Ruby starts writing things on the Mayor's coffee cups. It feels a little weird at first, and it sort of spikes a smidgen of fear in her the first time she scribbles a note on the side of the little brown cup, but thankfully, Regina doesn't snap at her for it. Hell, she doesn't even seem to notice, really. Ruby continues writing messages for her anyway.

The first one is simple. Start every day with a smile. Sweet. To the point. Cheerful. She even draws a smiley face next to the words, right before Regina snatches the cup from her hands and stalks out of the diner.

The second note is much the same. Short and sweet. I hope you have a great day, Mayor Mills. Again with a cute little smiley face. Again, right before Regina plucks the cup from her hands and walks briskly away without giving her a second glance. Ruby wonders if she actually realizes there are words there. If she ever reads them. If she smiles as she's walking down the sidewalk. Her curiosity alone is enough incentive to keep the notes going.

The next few are little more than a few words, hastily scrawled in less than perfect handwriting, since Ruby's in a rush. And still, she's pretty certain they go unnoticed.

Regina has a routine. She comes into the diner every morning, at promptly 7:45. She orders coffee. Black. Takes two packets of sugar. It's a little easier once Ruby learns it. She makes time to write her notes on Regina's to-go cups, and because of that, those notes get a little lengthier. The very next one reads: "Count your life by smiles, not tears." And Ruby writes it in bigger letters with a Sharpie right on the side of the cup, over the logo. She wonders if Regina will get that it's a Lennon quote. She hopes so.

If Regina notices, she still doesn't say anything.

It's starting to get a bit frustrating by the tenth note. Ruby's taken to writing some of her favorite song lyrics and quotes she finds herself looking up online when she has the time. It's a little ridiculous, but it's sort of become like a mission. Operation Make the Mayor Smile. Or something to that effect. Ruby knows there's got to be something sweet and appreciative lying below the surface of the Mayor's icy facade. She tells herself she just hasn't found the right words to get to it yet.

Ruby finds a quote one night, after spending an hour on a website that she thankfully stumbled upon a few days earlier. It's quite fitting, she thinks, so she writes it on the Mayor's coffee cup the very next morning. Happiness is a risk. If you're not a little scared, then you're not doing it right. She thinks it's clever, and, well, it really suits Regina. Ruby may not know her very well, but she's pretty sure the Mayor has some issues with letting herself be happy. Letting herself show that sort of weakness. Ruby doesn't think it's a weakness at all, but then again, she and Regina are two completely different people from two totally different backgrounds.

When Regina still fails to acknowledge the note, Ruby comes very close to screaming at her. Not in a rude way. She just wants to point it out. In a very loud manner. To make Regina take notice. To get a reaction out of her. Any kind, really. Even if Regina hated the notes, the least she could have done was say so. Ruby finds it more offensive to be ignored. Everyone else likes her scribbled randomness. So, why can't Regina?

Again, Ruby reasons that maybe she just hasn't found the right words. Operation Make the Mayor Smile gets a lot more serious. There's one thing about Ruby - when there's something she wants, she's always been good at tracking it down, by any means necessary, and this is no different.

After wracking her brain for fifteen minutes and coming up with nothing - well, nothing short of ridiculously corny quotes and lines from songs that she's sure Regina would know nothing about - Ruby comes very close to just giving up. She hears the bell on the front door jingle, and then the distinct sound of Regina's heels clacking across the tile floor, and at the last minute, she settles on something. She scribbles it down quickly on the brown cup and then hauls ass to fill Regina's order. Regina takes her cup from Ruby and eyes her curiously for a moment, taking note of the thousand-watt smile that's plastered across the younger woman's face. It's a little too bright, but entirely real, and when Regina remembers to mutter a quick 'thank you' before turning to leave, Ruby only smiles even bigger.

It takes a full five minutes - five long, agonizing minutes - for Regina to come back into the diner. She quickly makes her way to the counter, where Ruby is just cutting into a freshly baked red velvet cake. Regina sets her coffee cup down with a little too much force, and the noise startles Ruby. Hazel eyes snap up and Ruby's sure she's never seen Regina look so annoyed. It makes her breath catch in her throat and her heart stutter in her chest.

"What is this?" Regina asks, sounding none too pleased and pointing down to the cup. Or, more specifically, to the black letters Ruby had written there.

Ruby falters for a moment before she finally manages to answer, "Um, just, you know, something nice. That I wrote. For you."

Regina rolls her eyes. "I didn't ask for this."

"Oh. I know. It's just... something that I do. I do it for everyone. I was just trying to be kind."

"Do I look like I need your kindness?"

"Well, sort of. Yeah, actually."

"Excuse me?"

Ruby knows she should just promise to never do anything like this again and just shut her mouth and go back to work, but something won't let her. And so, instead, she says, "You never smile. You always look so angry when you come in. Or exhausted. Or just... bored with everything and everyone. I was just-I just wanted to be nice. I thought maybe you could use something to cheer you up. It wasn't meant to be offensive. And how anyone would find that offensive is beyond me, Madame Mayor." The words come out sounding a little more defensive than Ruby intended, but she's confident that they will get her point across.

Regina is quiet for a moment. She's chewing on her lower lip, and for a brief time, Ruby's afraid she's going to snap at her again. But then her face softens, just the slightest bit, and when Regina looks up at her again, there are tears in her eyes. Honest to God tears and a hint of red in Regina's cheeks, and Ruby has no idea what to make of that.

"I-I'm sorry. I didn't mean to-I don't know what I was-" Regina struggles to get the words out, and in the end, she fails. Miserably. She averts her eyes down to the coffee cup still sitting on the counter, to the message written on it. Smile. You are beautiful. Four words. So simple, and yet they had stopped Regina cold. Taken her by surprise.

"It's okay," Ruby says, reaching across the counter to lay her hand over Regina's.

Regina flinches at the touch, but she doesn't pull away. She looks up, catches Ruby's gaze with her own, and the smile Ruby gives her then would be enough to render her speechless if she wasn't already.

"I really didn't mean to overstep any sort of boundary or anything. If I did, I'm sorry. I just like making people smile, and I thought maybe I could do that for you, too," Ruby continues, and there's an obvious sincerity in her voice, a warmth that mirrors that in her hand, which is now clutching Regina's tightly. "I think you deserve that, you know." When Regina looks up at her, puzzled, she clarifies, "To smile. To be happy. I know things have been difficult for you lately. I can't imagine what you're going through and I know I can't fix it, but I can offer you this. It's not much, but if it makes you smile, just once, isn't that enough?"

Regina hates that she's struggling to fight back her tears. They burn hot in her eyes, and there's this sort of clenching in her chest, a flutter in her heart, that makes it that much more difficult to keep from crying. It's so strange and so unexpected that Regina finds herself at a loss. For words. For breath. It's the first time in ages that anyone has shown her this sort of kindness. Any kindness at all, really, and it's so genuine that Regina can't even refute it. That it's coming from Ruby is completely inconsequential. All that matters at the moment is the fact that Regina very much wants to believe that she does deserve to be happy, and maybe, just maybe, someone else finally sees that too.

"Mayor Mills?" Ruby asks softly, growing concerned the longer Regina's silence drags on. "Regina?"

Regina blinks, looks up into Ruby's warm face, and she smiles. It's small, faint, but it's there, and it's beautiful.

"Oh," Ruby breathes out, her own lips twitching up. "Look at that."

Regina can't help the way her smile grows, blooming until it lights up her eyes. It feels sort of strange, but not in a bad way, and so she lets it take over. Lets the feeling spread throughout her, lets it wind its way to her heart.

"Thank you," Regina says, a little shaky and still somewhat unsure.

"Any time," Ruby tells her, brushing her thumb over Regina's knuckles before she pulls her hand back.

Regina almost misses it. The touch. The warmth. There's a way to get it back, she knows, but she's not quite ready for that yet.

"I have to get to work," Regina says, shaking herself mentally. She needs to get a grip on her emotions, lest she make a fool of herself here, now. "I-thank you, again."

Ruby nods. "You go. Have a good day. And remember what I said, okay? Don't be afraid to smile."

"I won't," Regina assures her, before she grabs up her coffee again and heads for the door of the diner. She's just gripped the handle when something makes her turn back. Thankfully, there's no one else in the diner now, because she's fairly certain her next words would throw them all for a loop, and perhaps give away the fact that she is human just like the rest of them, no matter what they may think. "I did notice, you know. The others. The notes. I just didn't know what to make of them, so I didn't say anything," she confesses.

Ruby just smiles. "That's okay. You know now."

"Yes. Yes, I do. And maybe you're right. Maybe it is enough," Regina says, and just like that she leaves. She makes her way out into the brightness of another day, but there's a smile on her face and a lightness in her heart that lets her know things are well on their way to changing. And thankfully, for the better.