Dear Diary

Chapter 5

A/N: hey guys! I know this update is late. Life has been so hectic! But all great things! Hope you enjoy this chapter. Thank you for the support.

I read my moms diary again last week. She doesn't know that I know her and Emma are going on a date tonight. It's actually really exciting. I don't know what they're doing cause she didn't say but in this town it's not hard to find anything out.

So after my mom leaves to go pick up Emma, I'm going to get on my bike and follow them. I obviously have to make sure the date goes as planned.

These two are obviously meant to be together. They're true loves. I can just tell. They've already kissed. (Gross) Which my mom also doesn't know that I know. Even though Emma is a part of Operation Swan-Mills, I decided not to tell Emma that I've still been reading her diary. I just want Emma to realize the rest of this stuff on her own. They're both practically in love already they just have to figure it out.

Mom is scared. I don't think she has ever dated a girl before. I mean she could've but it doesn't really seem like she ever has. Not that I would ask her because ew.

This is so exciting. I thought as my mom walked into my room. "Henry. I'm going out for a little bit okay? Ruby is going to be downstairs incase you need anything." Regina said. "Mom, for one, I'm too old for a babysitter. I'm going to be a teenager in a month. For two, where are you going? You're dressed different." I said to her. It was true. Instead of he usual dressy clothes she wears, she was wearing a pair of black skinny jeans with a black shirt and a black jacket. She looked at me and did that thing with her eyebrow she always does when she's suspicious of something. "What? You just look really nice is all." I played it cool. She smiled. "Thank you Henry." She paused. "Oh and you're not getting out of having a babysitter. But don't think of it like that. Just think of it like hanging out with an older friend." She said shutting the door.

I laid back in my bed and huffed. This is going to be rough. How am I going to get out without Ruby noticing? I stared at the ceiling trying to plot a way around my babysitter. I shot up out of bed as it came to me. I can invite Ruby in on the plan and she can drive me to wherever their date is! It's the perfect plan.

I ran downstairs in a hurry, not realizing my mom hadn't even left yet. "Henry Daniel Mills. You're not an animal. No running like that in the house." Mom shouted. "Oops. Sorry mom." I shrugged. She was standing by the counter in the kitchen so I sat down on a stool across from her. I watched her playing with this old ring she always keeps around. It's always been a habit of hers to pull it out when she's nervous or thinking a lot. I watched her mess with it while she stared off into space.

"Mom" I said and she jumped obviously surprised by my voice. "Sorry. Are you okay?" I asked. She didn't answer right away. Instead she took a moment to really think about an answer. "I'm okay. Why are you asking?" She put on her best front. I responded, "you never play with that thing unless something is wrong." I pointed to the little piece of metal between her fingers. She looked down and stared at it for a moment. Without saying anything she walked to her study. I assumed she was putting it back in her hiding place.

She walked back out within seconds just as there was a knock on the door. My mom opened it with the best fake smile she could mask. "Ruby, come on in." She moved to the side to allow Ruby room to pass her. "Thanks Mayor Mills." Ruby said. "Sup Henry? Ready for a night of video games?" She shot at me. "Always." I shot back.

My mom walked in rolling her eyes. "Okay children. Have a fun night. Stay away from sugar and don't be up too late. I shouldn't be very late myself." She walked to me for a hug and a kiss goodbye. Then she gestured to Ruby to follow her to the entry way.

I waited until they were no longer able to see me and I hopped down of the stool. I tip toed over to the wall closest to them so I could listen in. "I will be at the bowling alley tonight, okay? I won't be checking my cell phone so if it's absolutely an emergency just call the alley for me. I don't think that I'll be too late." Ruby smiled and said okay. "Have fun on your date." Ruby chuckled when my mom gave her a glare.

Okay the bowling alley. Easy enough. It's not weird that my mom is taking her there. My mom has this secret thing for bowling. She never tells anyone about it because she's not very good. It seems like something Emma would like too since she's basically a big kid.

The Lanes is only a couple of blocks away. Ruby and I could even walk. I wonder how hard it's going to be to talk her into this, I thought. I heard he door close and Ruby's footsteps behind me. I spun around and smiled at her sweetly.

"Dude what's with the smile?" She asked. "We're going to the bowling alley." I answered. "If your mom wanted you to go with her she wouldn't have asked me to come over." Ruby said. "Listen, I've been trying to get my mom and Emma together and they don't know that I know they're going on a date tonight. I just have to go and make sure everything goes okay because neither one of them will tell me." I rambled. Ruby smiled. "Let's go! Go get a jacket!" She said. I can't believe it was that easy.

Ruby and I jumped into her car and drove off the the alley. I saw the black Mercedes that mom drive in the parking lot. I looked through the doors to the building and I could see the two of them standing at the counter. My mom pushed money to the cashier and Emma smiled. I could read her lips as she said thank you.

We waited for them to walk to a lane and sit down at the table behind it. "If we walked in now and went straight to the arcade, they wouldn't see us." I said hoping out of the car and walking to the doors. Ruby took a few to catch on but eventually she was next to me. I opened to door and we quickly snuck in and into the game area of the bowling alley.

There was a window that looked directly to wear my mom and and Emma were seated. The bowling alley was loud so it was impossible to hear what they were saying. I could see them smiling and laughing though. Emma was drinking a beer and my mom was drinking something too but I have no idea what it is. A worker brought out a pizza and set it in the middle of the two and Emma immediately jumped on it. My mom laughed so hard.

I couldn't help but smile at the two. "Looks good to me." Ruby said patting me on the back. "They're so meant to be." I smiled.