A/N: The fact that Shermy Pines does not show up on the character list is downright criminal. Let's remedy that.

Gravity Falls is owned by Alex Hirsche. I am not Alex Hirche.


Part I: Childhood

Chapter 1: The Talk

Filbrick Pines was never an easy man to read. From his dark sunglasses which no one could ever get him to take off, to his straight lined face, one could never tell what the man was thinking. He didn't frown much, unless he was extremely angry or disappointed. Smiles were even rarer.

Now imagine being six years old and having this man as your father, but it's even worse than that. Imagine being six years old, having Filbrick Pines as your father and being told by said man that he needs to talk to you. Needless to say I was extremely nervous.

I sat on the edge of my small twin sized bed, wrinkling the blue checkered sheets in the process. I stared at the clock realizing that time was not going correctly. Surely hours have passed, but no, it wasn't even five minutes. I rose from my bed and began to pace the hardwood floors, asking questions that any six-year old in my situation would.

What did I do wrong?

How much trouble am I in?

How much trouble would I be in if I ran away?

I knew asking that last question of myself was pointless. After all my room was on the second floor, and by age six I had learned that falling hurt, especially falling on concrete and cement that was right outside your own home. I paced my room for several more hours; I looked at the clock again, er minutes before without any announcement at all Filbrick Pines, my dad walked into the room.

"Dad, I'm sorry." I cried trying to hold back tears.

My dad looked at me, sighed, and then pinched the bridge of his nose. "Sherman, you're not in trouble. I just need to talk to you about something." He then walked over to my bed and settled his massive frame onto my tiny bed. He gestured by patting next to himself. "Come and sit."

I walked quickly to where my dad had beckoned me. Though time seemed to have no meaning when it came to my dad, I knew that he didn't like to be kept waiting. I sat down next to my dad and nervously waited for my dad to start talking. But the only sound I heard was the clock ticking and tocking.

Tick tock

Tick tock

Tick tock

I looked down twiddling my thumbs. I also knew that even though dad did not like to be kept waiting, he didn't like people rushing him even more. Then without any preamble he got up and headed out my bedroom door telling me to "wait here" in the process.

So wait I did, and in the process of waiting I could've sworn I heard yelling. Well not really yelling. My dad didn't yell. He spoke loud with a stern voice, while my mom screamed.

"Did you tell him?"

"No, why can't you do it? You're his mother?"

"Don't try to wriggle your way out of this Filbrick. You're Sherman's father, now act like a man and tell him!"

This time I heard my dad coming. I straightened myself on the bed and watched as he slowly made his way to my bed. His shoulders were slightly slumped. If there was one person that made my dad afraid it was mom. On the inside I was grinning ear to ear, on the outside though I had a straight face.

My dad sat next to me on the bed and unlike last time he began speaking immediately. "Son, your mother is pregnant." Before I could ask what that meant he continued. "That means you are about to become an older brother." He sat in silence for a few moments allowing me to digest the information that I had just heard. I was a mixed bag of emotions. On the one hand I was excited; I had always wanted a sibling. On the other hand I didn't think that I was going to get that puppy I was going to ask mom for my birthday.

We sat for several more moments before my dad began to speak again. "It also means that for the next seven months be careful around your mother. Never call her fat or even think it." He let out a slight shudder. "Women can always tell what you're thinking."

We sat in silence for a few more moments. However my six-year old self was both intrigued and confused by the idea of pregnancy. "So?" I began, "how is mom getting me a little brother by being pregnant?"

My dad raised his eyebrows. Then without any preamble as far as I could tell, asked the most bizarre and out of the blue question possible. "Son, what do you know about girls?"

"Girls?" I replied. "They're the ones with cooties right?"

With that my dad rose his massive frame off my bed and without saying another word walked out of my bedroom, closing the door behind him. It wouldn't be until years later that I would learn what my mom wanted my dad to talk to me about. And it was also years later when I would appreciate that he didn't.


A/N: As you can see this story will be about Dipper and Mabel's grandfather Shermy Pines. I am in the camp that believes that Sherman is an older brother to Stanford and Stanley Pines, while the baby shown is a red herring. The story will be told from Sherman's point of view. If you have any ideas for future chapters or writing tips please leave a review. If you would like to beta this story please PM me.