A/N : Warning- Time jump. I'm not the best with writing the build up of a relationship. So, their relationship has already built up and their relationship will continue to grow. Chapter 2

It's been about 2 years since David found Emma. Emma is in her home room with her best friend- Ruby- at school.

"So, Rubes. I have an idea." Emma told her best friend. "My dad needs a girlfriend."

Ruby smirked. "I'm in." She said. "Do you have someone in mind?" Emma directed her eyes towards their teacher, Miss Blanchard. Ruby smiled. "Oh my God!" She squealed.

"Girls quiet down. Pay attention." Miss Blanchard told the best friends.

Ruby leaned over. "Dude. Yes." She whispered and they both smiled.

"As I was saying, quarter 1 parent-teacher conferences start tomorrow. You guys can come anytime from 8:30-6:30." She told her students. "Feel free to talk amongst yourselves until the bell rings."

"So, why the sudden interest in getting your dad a girlfriend?"

Emma sighed. "He just seems lonely. I know he has me now, but he deserves more." She told her, shrugging. "Plus, I'm pretty sure he likes her."

"I doubt he even goes through with asking her. Granny's been trying to get him to ask her out since like, forever."

Emma smiled. "10 buck he does it. I just have to say please and give him my- as he calls them- adorable princess eyes, and he'll agree. It works every time."

XXX

Emma and Ruby were leaving track practice and their temp supervisor, also happened to be Miss Blanchard, she is also Emma's home room and math teacher. The track coach has been sick for the past week, so Miss Blanchard offered to supervise while he was out.

"Bye Em. See you monday." Ruby said and left.

Emma walked over to Miss Blanchard. "Where's your dad Emma?" She asked.

"On his way." Emma looked over at her teacher. "I have a hypothetical question." She told her teacher.

"Okay. Shoot." The teacher said and began drinking her water.

Emma smiled. "Hypothetically, if there was a guy… about your age, and attractive guy. He's pretty successful… hypothetically successful. Would you… hypothetically say yes, if this guy were to… ask you out."

Miss Blanchard nearly choked on her water. "I'm sorry, what?"

Just then her dad pulled up in his truck. "That's my dad. Bye Miss Blanchard." Emma said and ran off to get in the truck with her dad. "Hey dad. How was work?"

"It was great. How was school? Practice?"

"It was good. Don't forget, we have conferences tomorrow."

David nodded. "And uh… Miss Blanchard will be there?" He asked casually.

"Come on Dad. Just admit it. You like her." David just rolled his eyes and drove the rest of the way home.

XXX

"Just ask her on a date. Please! You need a girlfriend. No, you deserve a girlfriend, dad. And you can't even deny that you like her!"

David groaned. "Fine. One date. I'll ask her once. If she says no, then no." He relented. "Now before we leave for the conferences, do I need to be concerned about any of your grades?"

Emma scratched behind her ear sheepishly. "Maybe?" She mumbled.

"Really?" He asked shocked. "Okay, which one… or ones?"

Emma sighed. "I literally have an A in every class, except math. In my opinion, it's pointless." She added.

He couldn't really disagree with her on that point. "Well, how bad is the grade?"

"It's… passing." She told him. "Time to go! Rubes is already there."

XXX

"Hello Mr. Nolan."

David shook his head. "Please, call me David."

"Okay, David. We need to talk about her math grade." Miss Blanchard told her father. "It's not great." She said glancing over at Emma.

David looked over at Emma, then back at the teacher. "She told me it was passing."

Miss Blanchard shot a somewhat disapproving glance towards Emma. "Technically, yes. She's passing, but barely." He told Emma's father. "She has a D-." Her teacher informed. "If it goes much lower, I'll have no choice, but to bench her until it gets back up."

David thought for a moment. "Wait. I got an email-"

"About the tutoring program I'm starting?" She asked and David nodded. "I was just about to suggest that."

Emma shook her head. "No way. 5 hours of math a week is plenty for me. No thanks." She looked over at her dad. "I am not getting tutored." She told him.

"We'll talk about this at home." He told her firmly.

She rolled her eyes. "Whatever." She scoffed. "I'm gonna go find Ruby." She said getting up.

"Em-" He started, but she was already gone. He turned back to Emma's teacher. "I'm sorry about her."

The teacher smiled understandingly. "It's completely fine. She's a teenager."

David scratched behind his ear. "I'm going to ask you something." He told her.

"Okay..."

He chuckled. "My daughter seems to have picked up on a small crush of mine. She practically begged me to ask sed person out on a date."

Suddenly Miss Blanchard was getting a flashback of that 'hypothetical' question of Emma's yesterday after practice. "This person is…?" She asked, blushing.

"You."

The raven haired teacher laughed. "This explains yesterday." She said to herself and david raised an eyebrow. "Emma asked me a hypothetical question." She started. "She asked if an attractive successful guy were to ask me out, if I would say yes." The teacher told the sheriff.

"Purely hypothetical, of course." He joked. "Well? What do you say? Go on a date with me Miss Blanchard?" He asked, with a slight blush in his cheek.

She smiled. "Only if you call me Mary, instead of Miss Blanchard." She said, writing her phone number down on a slip of paper.

"Deal." He told her with a smile and then he was handed the number. "Is there like a signup sheet for the tutoring? If I don't sign her up now, she'll be able to beg her way out of it." He told her and she chuckled, handing him and sheet of paper. "She has these eyes. All she has to do is say please and use her eyes, and I'm screwed." He joked.

Mary laughed. "She's got you wrapped around her finger, doesn't she?"

"Indeed she does." He looked down at the paper and saw one other name on it. 'Killian Jones'. Graham's nephew, not a bad kid, but tended to find trouble.

"Since track practices are on Tuesdays and Thursdays, tutoring sessions are on Mondays and Wednesdays." Mary said, disrupting him from his thoughts.

XXX

David and Emma had been arguing about the tutoring for half an hour. "Emma. The tutoring is necessary."

"I don't care! It's not fair!" She yelled. "Did she leave out the part about how the tutoring is optional?"

David sighed. "No Emma, she didn't leave that out. The difference is that you need the tutoring." He said calmly. "You're barely passing her class. So, unless you want to be benched from the team-"

"That's not fair! Because I'm almost failing one stupid class! What about all my other classes! It's not like math is an easy subject." She mumbled.

David sighed. "Princess, that's why you need the tutoring." He told her. "It's non negotiable."

Emma rolled her eyes at the nickname he insisted on calling her. "Fine." She sighed. "I'm sorry for yelling at you dad. It's just, it's not fair. It sucks. Like math sucks." She said, then smiled. "Wait! Did you ask her out?"

David smiled and nodded. "I did. She said yes." He said and Emma squealed. "Oh, and I was pleased to know that you think I'm an attractive, successful guy." He teased his daughter.

"It was a hypothetical question!" She defended. "I need to go call Ruby!" he raised an eyebrow at the sudden urgency of Emma calling her best friend. "She owes me $10! She didn't think you'd do it."

"Teenage girls are… betting on me?" He asked. "That's… you know what, nevermind."

Emma laughed and ran upstairs to call her best friend.

"Ruby! You owe me 10 bucks!"

"No way. He did it?"

Emma nodded, upon realizing Ruby couldn't see her. "Yes! They're going on a date! I don't know any details, but when I do, I'll clue you in."

"You better!"

Emma laughed. "I can't believe my dad's actually going to have a social life now!" Emma yelled loud enough for her father to hear, he responded with a 'Hey! I heard that!' Which resulted in Emma laughing even more. Emma decided to change the subject. "You're never going to believe what my dad is making me do!"

"What?"

"Tutoring! It sucks!" She groaned. "I have to stay after on Mondays and Wednesdays now." She sighed. "It sucks."

Ruby laughed. "You mentioned." She said. "Are you busy today?"

"Nope. Why?"

"Mulan and Killian invited us skating tonight."

Emma groaned. "You know my dad hates him Rubes. And I very strongly dislike him. He's so full of himself. It's annoying."

"Please Em. This is my chance to ask her out. Do your best friend a favor?"

"Fine." She relented. "But you owe me and," she lowered her voice, "My dad doesn't know."

You could practically hear Ruby's grin through the phone. "Thank you! You're the bestest best friend ever!"

"Yeah yeah, yeah. What time?"

"Starts at 8:30."

Emma groaned. "That's in 2 hours Rubes. I need to shower. I'll see you later." She ended the call.

Emma ran down the stairs to tell her dad about skating. "Hey dad. Mulan invited Ruby and I skating tonight." She told her dad- leaving the fact that Killian will be there- out.

"Do you need a ride?"

She shook her head. "No, I'll probably go out for a run before I head to the rink anyways." She told her dad. "I was just letting you know. I'm gonna go shower now."

XXX

After Emma went on her run, she ran to the skating rink and bumped into Killian. "Oh… Hey."

He smirked. "All hot and sweaty for me, love?" He asked cockily.

"Get over yourself." She said, rolling her eyes.

"Come on Swan. Admit it. I'm just devilishly handsome." He winked.

She rolled her eyes. "Not my name Jones. You know that." She walked over and put her skates on, Killian following suit. "Why are you following me?" She asked, annoyed.

"I invited you, remember?" He quipped. "Where's Mulan and your friend anyways?"

Emma smiled. "Probably making out somewhere." She told him. "The only reason that we're here is so it wouldn't be an official date. Not yet anyway." She informed him.

"Maybe it could be a… double date." He said, more seriously. Emma spun around quickly to look at him, almost falling, but Killian caught her before she could. "Woah. Careful Nolan."

"What'd you just say?" She asked him, mouth agape.

He scratched behind his ear nervously. "Uh… do you wanna go on a date… with me, Emma?" He asked her nervously. "If you want to. I mean, I guess we don't have to. But we could be friends, ya know? Or more than that, if you'd like?"

His nervousness got Emma to smile and unexpectedly, she actually said, "Yes."

"Really? What about your dad? Oh my God your dad hates me." He said face turning pale. "He's never liked me. He tells me he doesn't like the way I look at you."

Emma was smiling, until that last sentence. "He said what?" She asked, not sure if she should be annoyed or amused.

"Never mind that. When shall this date occur, love?" He asked. "Friday? 7?" He asked her.

Emma nodded. "Friday at 8 sounds great Killian." Emma started looking around the room until she spotted her best friend with Killian's best friend. "I'll see you later. I'm gonna go talk to Ruby." Emma skated out and stopped next to Ruby and Mulan. "I need to borrow her." She told Mulan and skated off with Ruby. "Oh my God."

"What was that all about?" Ruby asked her.

Emma stared blankly at her best friend for a moment before answering. "I just agreed to go on a date with Killian. On Friday."

Ruby's eyes widened. "I thought you didn't like him."

"I don't know anymore." She groaned. "He asked me and I was gonna say no, I really was, but then I didn't." She admitted. "It's like all at once he got cute. It was actually adorable." She told her friend, blushing.

"It took you guys long enough!" She all but shouted. "I've wanted you guys together since like last year!"

Emma just blinked at her friend in shock. "Seriously?!"

Ruby just laughed. "I'm not gonna be there when you tell your dad."

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