Woo

Dipper Pines could not flirt.

He was like a middle schooler with a crush; shy, awkward, and sweated a lot. He told himself he would have the courage to tell her how he felt someday. He tried to drop hints and attempted to flirt, but it always ended disastrously. Well, disastrously was too strong a word. If there was a word for 'I tried to get her to take a hint but I ended up being a nervous wreck in the end' then that was Dipper.

He was so sure that one day he would stop acting like the embarrassing love struck teenager that he was, but he so wrong. He would always be the awkward kid with a crush, just like he was with Wendy. No matter how many times he convinced himself that he would properly flirt with Pacifica, it never happened.

Dipper didn't even know why he got so nervous when he tried to hit on her. It was obvious they had a thing for each other, they had ever since they defeated the ghost in her mansion when they were twelve. They had been dancing around each other for three years now, since they both have reached the age of fifteen. And yet, both were far too shy and stubborn to make a move.

Dipper had waited and waited for Pacifica to ask him out first, since she was the more bold one. Everyday he woke up hoping that today would be the day. And ever night, he went to bed with the familiar disappointment.

He couldn't really blame her though, asking somewhat if they wanted to date was nerve wracking. He had learned that in his own experiences, especially when he had liked Wendy.

But now, Dipper was fed up with waiting. If someone was going to make a move now, it was going to be him.

He would have to swallow his anxiety and teenage awkwardness. It was going to be hard, but waiting three whole summers for something to happen was worse. He knew that if they got together, they could push past the awkward stages and get right to the romance.

But there was a problem.

The problem was not only his nervousness, but also how he was going to ask her.

Being the awkward kid he was, Dipper knew that it would be hard for him to casually ask her. Casually flirting with her had never gone in he direction he hoped it would, so asking her out in a casual manner would only end in more nervousness.

Still, he didn't want to be completely romantic. He was way too awkward for showing up at her doorstep with flowers and chocolates with a teddy bear that said 'be mine!'. Pacifica herself was not much of a hardcore romantic either, so it would be very embarrassing for the both of them.

An equal mix of casual and romance would work well, he decided. But what would be the perfect way to ask her with only romance and casualness?

He had seen a lot of romance movies since his sister, Mabel, often dragged him out of the shack to see them. He could probably pull an romantic situation out of a movie and make it more casual. There were many to chose from though, and he had to find the perfect one.

It wasn't until later that he saw the flaw in his plan.

He had arrived at her mansion at almost one in the morning. A back pack was hanging over his shoulder, and it looked like it held something heavy. Clenching his sisters grappling hook in one hand and gripping the back pack's strap with the other, he snuck around the gates of her house.

Dipper glanced around for any night guards, and was thankful to find none in his area. He stared at the giant wall that blocked him from entering the courtyard. He aimed the grappling hook at the top of the wall, and shot it.

As he was stealthily climbing up the tall wall, he silently thanked his sister for deciding on keeping the tool from the Mystery Shack all those years ago. He had thought it was weird she wanted something like that, but now he was glad she had taken it.

Once he reached the top of the wall, he stared down at the ground below. It looked a good few feet away, and jumping down from the wall probably wouldn't hurt that much. Besides, he had done much more dangerous stuff while solving mysteries.

Dipper looked around once more for any night guards before jumping down. He put the grappling hookinto his back pack before creeping around the courtyard, crouching low. He was trying to find her room. It wasn't really too hard to find, he had been to her mansion a couple of times. Although her parents hated him and his 'kind', Pacifica always let them come over when her horrible parents were away.

Dipper frowned, remembering her parents. He had always hated them. It angered him that they treated her so poorly. They were terrible and abusive, especially to their daughter. Pacifica used to be horrible to, and Dipper used to hate her. Despise her, even.

But that was because her parents wanted to shape her to be just like them. Luckily, Dipper helped her say no to her parents. She stood up to them, and built her own personality.

At that party three years ago, he saw who she really was. She was kind, beautiful, and wanted to always do the right thing. And now, he had come to adore her so much.

Dipper smiled and blushed at the memory. He really was deeply in love with her.

When he finally reached where her room was located, he took the back pack off his back. Opening it, he pulled out a bunch of rocks. He gathered some in his arms before standing up. Looking up at the window a few feet up, he picked up a rock and aimed.

"I hope this is romantic and casual enough for her," He mumbled to himself before throwing the rock at her window. He threw too softly, so it hit the house a few feet down from her window before settling in the grass.

He let out an annoyed groan before picking up another rock. He thew it a bit more harder this time, but it didn't even reach her window. He kept throwing and throwing rocks, and called out her name every once in a while.

He had grown very frustrated when he only had one rock left. Not a single one had hit her window. Letting out an angry cry, he threw his final rock.

He hit her window alright. He just threw it too hard.

Once the rock made contact with the fragile glass, the glass shattered. He heard a loudclunk from inside the house. He guessed the rock must have hit the floor.

He stared up at Pacifica's broken window, horrified at what he had done. Not even a split second later did alarms start going off. Everything started to flash red. Dipper stood frozen in shock before yelling "OH SHIT!".

He scooped up his back pack and made a run for it. He grabbed the grappling hook and pulled himself up the wall. He heard night guards behind him, and fortunately got over the wall and jumped down just in time.

As he was running away far away from Pacifica's house, he knew that flirting was most definitely not his thing.


"You mean you broke her window?" Mabel said, cracking a smile. It seemed like she was having a hard time holding in her laughter. Dipper glared at her. His failed romance was not supposed to be funny. Mabel had many failed romances herself, so he expected her to feel sorry for him. But instead, she was just giggling at the story he was telling.

Mabel had found him sitting on the chair in front of the TV at nine in the morning. He wasn't watching television, the TV wasn't even on. He was just sitting there, looking gloomy. He had that 'my life is over' look on his face.

Of course Mabel was quickly concerned. Dipper looked like he didn't even get a wink of sleep- which he hadn't. She had sat next to him and asked him what was wrong, and now they were here. He was still upset that his plan hadn't worked and Mabel was laughing at his suffering.

"Yeah. I did. She probably hates me now," He grumbled, crossing his arms. Mabel stopped giggling, now seeing how upset he truly was.

"Why do you think that?" She questioned. Dipper sighed, and looked at the ceiling.

"Because I broke her window and probably got her in trouble,"

"But you said that you ran away just in time. She or anyone else doesn't know it's you," Mabel pointed out.

"But I broke her window. He parents have to know something's up by now!"

"No, you know how they are. They're probably yelling at the night guards as we speak, since they couldn't catch you. Besides, they have enough money to pay for the window," Mabel reassured him. Dipper shook his head.

"Still, I can't help but feel like she hates me now,"

Mabel was about to respond before a knock on the door interrupted her. She stood up from the chair, and walked towards the door. Dipper watched her go before sighing sadly. Pacifica would never date him at this point.

"Hey Mabel, is Dipper here?"

That voice. He knew that voice from anywhere. Dipper quickly jumped up from the chair. He tried to smooth out his clothes and fix his hair. Even if she was here because she was angry at him, he still had to look good for her.

Mabel and Pacifica appeared in the living room moments later. Dipper smiled and waved awkwardly.

"Hey Pacifica," He said nervously. Pacifica nodded in response.

Oh great she's angry at me.

"Well, I'll just leave you two alone," Mabel said, smiling knowingly. She left the two teenagers alone.

They stood in silence for a good minute. Dipper gulped, unsure if he should speak first.

"So, what are you doing here?" He finally managed to sputter out. Pacifica crossed her arms.

"I want to know why you broke my window," She said simply. Dipper's eyes widened, and stared at the floor fearfully.

"How did you know it was me?" He asked quietly. He didn't want to try and lie to her by saying he had no idea what she was talking about. It wouldn't help the situation in the slightest.

"Well, I saw you running away from my window. Your hat is really bright in red lighting, you know that?"

Dipper continued to suddenly be fascinated with the floor. He couldn't meet her eyes.

"I'm sorry," He said slowly. It went quiet once more. Dipper was afraid that Pacifica hated him now. She seemed to be very upset with him, so he expected the worst.

"You know, there are better ways to ask me on date, Dipper Pines,"

Dipper snapped his head up to look at the girl. She didn't look angry, she was smiling. He blinked at her, confused.

"W-what?" He asked, completely flabbergasted. Pacifica laughed and approached him. They were only a few inches apart.

"Well, throwing rocks at my window is a clear sign that you like me," She giggled. "Or, you really hate me."

"I could never hate you!" Dipper said. He blushed when he realized he basically just told her how he felt. Pacifica blushed too, and took his hand in hers.

"How about on Friday night we go out to eat for dinner? You can pick the place," She said, looking hopeful. Dipper smiled at her and nodded.

"Sounds good to me!" He said. Pacifica giggled. He was such a dork.

She turned around and started to head out the door. "Oh, wait."

She walked back to him and placed a soft kiss on is cheek.

"You got yourself a girlfriend now, after all these summers,"

Dipper blushed even more. A very happy look was on his face.

"Y-yeah. I like that. I like you," Dipper said. He scolded himself for being awkward, but stopped when Pacifica laughed again.

"I like you too,"

Meanwhile, Mabel watched the romance of Dipper and Pacifica unfold from the kitchen. She pumped her fist in the air in triumph.

"Finally!"


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