>Be in Equestria.
>P0nyville to be precise.
>P0nyville market place to be more precise.
>You’re buying some essential supplies for the weekend.
>Scootaloo’s going to be hanging out, her friends have previous engagements.
>That’s cool. You’re planning a picnic with Fluttershy and Rainbow.
>”Oh, hello Mr. Anon,” You turn and see the smiling face of Scootaloo’s teacher.
>You return her smile “Well hello Miss Cheerilee, how are you today?”
>She puts a few items in her saddle bag. “I’m doing well. I was actually wondering something.”
>You watch her as she pays for her items and offer to carry them for her. She declines, but what a nice thought.
>”Of course, ask away.”
>She looks down at the ground. “I was wondering if you wanted to join me for lunch tomorrow.”
>You nod. “Kind of like a parent teacher conference?”
>She looks up and nods at you. “Oh yes... something like that I guess.”
>You give her a friendly wink. “It’s a date then.”
>You walk away as she giggles to herself.
>Making friends smile and laugh, always a good thing to do.
 
>The next day, you leave Scoots at home.
>She says she has a project to work on anyways so you don’t feel bad for leaving her alone. Besides, she’s old enough to not need you around ALL the time.
>Damn it brain, I like to at least THINK I’m still needed.
>Cheerilee’s already waiting at the quaint outdoor cafe you’re quite fond of.
>”Good afternoon Miss Cheerilee,” You say as you take your seat.
>She smiles, she has a very nice smile. “Just Cheerilee is fine.”
>You smirk and give a wink, “In that case, Anon is fine for me.”
>The waiter comes and you order what you always do here.
>”So, how’s school... Scootaloo’s behaving herself I take?” You ask, taking a sip of your water.
>She nods. “Oh yes, I can see your influence in her. She’s very lucky to have a father who cares about her so much.”
>Awh that’s so sweet. You think you’re blushing. “Well thank you. I’m sure you’ve played just a big a part in making her who she is.”
>Aha, her turn to blush.
>The afternoon is spent chatting and laughing.
>You wonder why you haven’t done this sooner.
>Over dessert, she runs a hoof across the table. “Um... Anon, have you ever thought about... About finding somep0ny special in your life?”
>A... buh... what?
 
>The thought HAD to occured to you a long while back, but that’s been resolved. Resolved with Rainbow Dash.
>”Oh, uh why do you ask?” You’re blushing again, but for a different reason.
>She gives a little cough, avoiding eye contact. “Well... I don’t really have anyp0ny in my life... Just the children, they’re my life.”
>Uh-oh.
>She continues, “I know you’re good with kids... I was hoping you’d like to... you know...”
>You clear your throat. “Miss Cheerilee, are you trying to seduce me?”
>The reference goes over her head.
>Her eyes go wide. “Oh! No... I’m sorry if you got that impression.” She drops her head. “There’s just something appealing about a guy, regardless of species, who’s so good with children.” She sighs. “You’re the only single father in town, I just thought...”
>Oh man, you feel bad. You cut her off. “Listen Cheerilee, you’re a great mare. If I was an available stallion, I’d be very receptive....”
>She smiles and perks up.
>”...But I still don’t think I’m really into p0nies like that.”
>She nods as her smile fades again. “I know. I just... Get so lonely sometimes, I though you’d feel the same. Then again, you already have a wonderful p0ny in your life.”
>Oh man, who’s been talking? Rainbow messing with you again?
>She gives you an honest smile. “Scootaloo’s very lucky to have you.”
>Oh, right. Scoots.
 
>You get home and.... Scootaloo’s built a kick ass ramp out front.
>The dad in you should be pissed, but you kind of want to see her jump off it.
>She greets you at the door and you congratulate her on her architectural accomplishment.
>”How was your lunch?” She asks as she pulls her scooter out to test out her ramp.
>”It was good... Miss Cheerilee is very nice.” You say, following her out.
>Scootaloo stops and looks up at you. “Are.... Are you two dating now?”
>You look down at her. Maybe it’s what she wants? Maybe, just maybe, she actually DOES want a mother around all the time.
>”I don’t know sweety, for now we’re friends.”
>What? She looks relieved. “That’s good. I see her enough at school, I don’t think I’d like her around all the time.”
>That makes you laugh. You understand what she means.
>”Yeah,” You say. “Besides, I have my hands full with you, I don’t think I need ANOTHER p0ny to put up with.”
>She laughs and playfully kicks at you. “Stop being so weird dad.”
>You nervously put your hands in your pockets. “I don’t know... I think it’d be nice to have someon... somep0ny around though. One that cared for me.”
>She looks up at you with... sympathy? “Then maybe you should.”
>You chuckle. “But you said...”
>She doesn’t let you finish. “She IS really nice, just like you... Maybe you should.”
 
__
 
>You spend the rest of the day in thought.
>Should you? You admit, you do sometimes feel lonely. You have Scoot’s, but she’s getting to the age that she doesn’t need you around all the time.
>The next day, you get ready for your picnic.
>Rainbow must have made sure you all had a nice sunny day.
>The four of you assemble and get to it.
>Which is to say, you all just sit around.
>Fluttershy thinks she sees a family of birds and takes off with Scootaloo.
>”Hey Dash?” You say, watching the sky.
>”Mmhmm?” She responds with a mouthful of food.
>You give a sigh. “I’ve been thinking of starting dating... finding a ‘special somep0ny’ and all that.”
>She coughs a bit at this stunning admission. “I appreciate the thought dude, but you’re not really my type.”
>You flash her an annoyed look. “This is serious, you know how I’ve been with the whole species barrier.”
>She pats your shoulder, “Dude, nop0ny sees you as ‘that human’ anymore. You’re one of us, you’re accepted. Integrate already.”
>You just nod. “When in Rome.....”
>”Have sex with the locals?” Dash finishes for you.
>You flash her an annoyed look “That’ so not how that saying goes.”
>She shrugs at you. “Besides, how many times have you slept with Applejack in the past?”
>Ok, conversation over.
 
>The rest of the weekend slips by.
>You take Scootaloo to school. Before you do anything, it’s best to ask her.
>”Remember when I went to lunch with Miss Cheerilee?” You ask.
>She chuckles. “It was only a few days ago dad, of course I do.”
>Cheeky girl. “Well, I was thinking of asking her out if that’s ok with you.”
>Why is she scoffing at you? “You’re an adult dad, you can see whoever you want.”
>You nod at that. “True, it’s just about what you said the other day and...”
>She stops and looks up at you. “How many years have you spent making sure I was safe or happy? I think it’s your turn.”
>All you can really do is smile. “I just don’t want you to feel like you’re being replaced.”
>She gives you that ‘I love you, but you’re being an idiot’ look. “I’m getting older... I won’t be around forever. You deserve somep0ny to have around and care about. Preferably one that cares about you too.”
>Damn it, she’s gotten mature. It’s not something you like to think about, but she will move out one day. Then where will you be?
>You thank her as you see her off at the school.
>Your eyes meet Cheerilee’s. You smile, she does not.
>Time to man up, behave brain, please.
 
>She greets all of her students as she attempts to avoid looking over to you.
>You clear your throat as you walk up to her. “Um, Cheerilee?”
>She finally looks up at you, a bit of sorrow in her eyes. “Yes Mr. Anon? Can this hurry, class is about to begin.”
>You nod. “Of course, I just have a quick question... Would you like to have dinner sometime?”
>She cocks her had a bit. “You mean you, me, and Scootaloo?”
>Smiling, you tell her. “I was thinking just you and me, together.... Is tomorrow night ok?”
>Any sadness that was in her eyes evaporates. “Oh... Yes, that would be great... I’d like that.”
>”I can meet you here tomorrow after school then. It’s a date.” You start to walk away and shout over your shoulder. “A real one this time, I mean it.”
 
>Shit!
>You’re going on a date. What do you even do? It’s been a while. Do these folk have special dating rituals?
>You must assemble.... A TEAM!
>When you tell Fluttershy you need help with your upcoming date, she takes off at the speed of light.
>Before you know it, Applejack, Rarity, Rainbow, and Fluttershy have you surrounded.
>”I’m so excited for you,” Fluttershy twitters. “What do you need help with?”
>You look to each of them and their smiling faces. “Well,” You start and take a deep breathe. “First, what do I bring? Flowers? You all eat flowers so is it like a box of chocolates? If I get one, do I need the other? Which flowers are tastier? Should I go for looks, or taste?”
>Rarity stops you with  a laugh. “Anon dah-ling, honestly... All you have to do is just lavish her with the finer things. Impress her as a connoisseur.”
>Fluttershy zips in front of her. “Noooo! All he has to do is be kind and caring and sweet and all lovely.”
>”Wrong!” Rainbow interjects. “You need to impress her with with a display of awesome! Just prove your coolness level and she’ll be all over you.”
>You look over to AJ because she’s the natural progression apparently.
>She gives you a smile. “Just be yerself. If that ain’t enough fer her, then she ain’t worth it.”
 
>The next day after school, you go to pick up your date.
>Huh, date, still seems weird to you.
>Rainbow shows up to make sure Scoots gets home ok. But before she goes, she trots up to you and Cheerilee.
>”Don’t worry Anon dude, I’ll look after her for you.” She’s sure to angle the next comment towards Cheerilee. “Just like that time at the....”
>Your stern gaze cuts her off.
>She chuckles and shrugs. “Eh, you should tell it, I wouldn’t do your awesomeness justice.” Damn that Rainbow.
>As she leads Scootaloo away, your charming daughter adds in, “Be sure to get him home by sundown and no funny buisness.”
>Cheeky. Oh well, at least she’s made Cheerilee laugh.
>You just shrug. “Shall we?” You say, motioning towards town.
>You two enjoy the slightly rustic walk into town.
>The birds sing, the squirrels bound in the trees, and Fluttershy flies right at you.
>Oh damn it.
>”Oh Anon,” She cries, carrying something in her arms. “It’s Angel, he’s so sick.”
>She holds out her arms and Angel lays draped in them, playing dead.
>You look at Fluutershy and she motions with her head down towards her bunny.
>You supress an annoyed sigh and reach down to pet the acting rabbit.
>As if by some ‘miracle’, Angel pops up and does a little dance.
>Fluttershy beams at you and turns to Cheerilee. “Oh thank you, he’s so kind. Don’t you think he’s kind Angel bunny?”
>Angel gives you an angry stare for a moment before putting on a smile and nodding.
>As Fluttershy flies off, you give a ‘I don’t know’ look to a very confused Cheerilee.
 
>You two finally make it into town.
>Rarity walks up, magicing two rolls of fabric.
>Double damn it.
>”Oh Anon, dear, JUST who I wanted to see.” She chimes, fluttering her eyelashes. I was just making up that de-VINE suit you mentioned, and might I say, what a unique and brilliant design. I was just wondering, which do you prefer, red, or the blue?” At each color mentioned, she shoves the respective roll into your face.
>”Uh...” You nervously utter. “The red i guess.” It’d be nice to know what suit she was talking about. You never mentioned one to her.
>Your answer must not have been to her liking because she gives a small disapproving grunt before composing herself. “Ah yes, the red will most definitely bring out your.... Eyes... Yes eyes.”
>She turns to a, once again, confused Cheerilee. “Isn’t he so charming? And with a wonderful eye for the finer things.”
>After she leaves, you break the silence. “I could REALLY go for that dinner right about now hehe.”
>Before you two can move though, you see Applejack.
>All the damn its.
>As she walks by, she gives a nod. “Anon, Miss Cheerilee.”
>You two greet her back as she goes about her merry way.....
>WTF?
 
>Once you two get to the restaurant, you feel the need to apologize. “I’m sorry about earlier, my friends have it in their crazy heads that I need to do... SOMETHING for you to like me.”
>”Oh,” She giggles, she has a cute giggle. “I really don’t think I’ll need much convincing.”
>You shuffle in your seat a tad. “Well, I’m not exactly the MOST stable guy.”
>She waves a dismissive hoof at you. “Oh please, you’re probably just being your own worst critic.”
>You take a deep breathe.
>No, dude, don...
>”At least once a week I wake up in a cold sweat, just wanting to scream. There are also certain things that make me.... remember things.” You just begin to vent.
>She nods. “From the war right? Scootaloo’s talked about that before. She was worried about you.”
>Despite that, you have to keep going. “I’m recovering from alcoholism... I resorted to drinking to deal with my problems.”
>I swear, if you bring up AJ, I’m out.
>Okok brain, I think I’ve detracted her enough.
>”Oh you poor dear.” She reaches out and puts her hoof on your hand. “I had no idea things were that hard for you.”
>She.... cares? The emotion in her eyes isn’t just idle sympathy, but empathy.
>Despite what you’ve told her, she smiles at you. “Thank you for being so honest with me.”
>the evening goes by fast. You two laugh so much, the other patrons start scoffing and huffing, but neither of you care.
>After seeing Cheerilee home you get into your front door.
>Scootaloo’s waiting up for you. The sun just barely disappearing on the horizon.
>”So.... How was it?” She asks with a sly smile.
>Your smile is wide, noticeable, and you don’t care. “It was..... nice.”
>She cocks an eyebrow. “Nice?”
>”Mmmhmmm, very nice.” You’re already planning your second date.