Dear Mr. Pessimist {Completed}

By ChasingMadness24

720K 34.5K 6.1K

"Dear Mr. Pessimist, here are a few reasons to love yourself and the world." When Sydney Hale gets a j... More

AN/COPYRIGHT
Cast
Banners
Trailer!!! (and fanart)
Playlist
Prologue
~1~ Here's Some Advice, Cupcake
~2~ Burnt Toast
~3~ Cutie Pie
~4~ Mr. Pessimist and Ms. Optimist
~5~ I'll Beat You With A Biscuit
~6~ Bite Me, I Bet I Taste Amazing
~7~ You Smell Like Cookies
~8~ You Smell Like Cookies Pt. 2
~9~ Who Got Your Knickers In A Twist?
~10~ Stressed Is Desserts Spelled Backwards
Update?
~11~ Bittersweet Victory
~12~ In The Air Tonight
~13~ Sweet and Sour
Just a Quick Authors Note
~14~ Beat Me, Break Me
~15~ Bitter Batter
~16~ I Seriously Need Some Therapy Cake
~17~ Take My Hand, I'll Show You How To Dance
~18~ Please Forgive Me, I Have Pie
~19~ Chocolate Chip Muffins On A Rainy Day
~20~ That's Not My Cookie
Need Help
~21~ My Pillsbury Doughboy
~22~ I'm Here All Night
~23~ Chocolate Berries and Sad Songs
~24~ Stay Here Forever
~25~ Every Little Piece
~26~ Wedding Bells
~27~ Forget About The Brownies
~28~ Sydneys
Sequel?
New Book (Bonus Chapter)
I Do (Bonus Chapter)

Epilogue

16.5K 884 134
By ChasingMadness24

"Sydney!"

I jumped back from the textbook in my hands at the sound of Bennett's voice. I turned around to find him walking toward me, the glasses the eye doctors had forced him to where, starting to slide down the bridge of his nose.

"Hi." He kissed me quickly before leaning over my shoulder and seeing what I had on the computer screen.

"Why is there a sperm donor website open in another tab?" He sound partially amused and partially curious.

"I'd like to know the same thing. Who was the last one to use the laptop before me?" I asked, staring up at him. I felt my face twist in disgust when I realized who it had been.

"Oh God, Bennett. Wasn't it your mom?" His head whipped up, his blue eyes huge behind his dark rimmed glasses.

Bennett's parents had gotten divorced a little over a year ago, leaving most of the money in Mr. Banks possession. I had forced Bennett into help his mom out despite his protests. We would occasionally drop by the house with Parker and occasionally Erin whenever we had extra time.

"That's the most disgusting image I think I've ever had in my head." He shuddered dramatically and walked over to the swing where our eight month old son was sleeping.

"I can think of worse." I joked, closing the textbook in my hand and stretching.

"I don't want to hear them." He replied.

"What about the time Tristan-"

"I don't want to hear it, Syd. This is my mom trying to get pregnant, it's just gross." I laughed, shutting my laptop as I cleared the desk.

"You got work tomorrow?" He asked, muttering something to our son as an after thought.

"Yeah. I get to spend another wonderful day with a class of obnoxious, delinquent teenagers." I said, coming out a lot more bitter and sarcastic then I had intended it to be.

I really did love working with the kids, even if this was my first year, I had already had a blast seeing how I could change some of their lives.

"And, Bennett, sweetie." I said, stopping in front of him to kiss Parker's forehead, "Twenty-six year old men don't think their mom's trying to have a baby is gross. They should think it's great."

*

I shifted Parker's carrier into my other hand as I waited outside of Jess' house, tapping my foot anxiously.

"Auntie Syd!" The seven year old boy threw his arms around my legs and stared up at me with big brown eyes.

"Hey there, Nicky." I said ruffling his hair as he moved on to look at the baby boy in the carrier.

"He's so big now." He exclaimed, making gestures with his hands. I laughed, nodding.

"You are too, kiddo. I remember when you were as big as Parker." I replied, "Where are Mommy and Daddy?" He shrugged, clapping his hands together.

"Mommy said she has erdans to run."

"Errands." I corrected him. He frowned, crossing his small arms over his chest.

"Daddy is in his office. You can come in." By the time Nicky had moved into the house, Tristan was in the living room, feet away from the door.

"Sydney? What are you doing here? Is Ben with you?" I shook my head as he shut the door gently behind me, his hand lingering on the door knob.

"I came over to talk to Jess about the wedding, but Nicky said she isn't here." I sat on the loveseat, reaching down so Parker could tug on my fingers.

"She should be back pretty soon. You want anything to drink?" He questioned, his hazel eyes on me.

"I'm good, thanks." He nodded, grinning as Nicky hopped after him into the kitchen for juice.

I had been beyond surprised when Jess had agreed to move to Massachusetts with Tristan for the four years he wanted to spend down there. They had moved back here after five, and despite the fact we had seen them pretty often, it was nice to have them back here in town.

"How's Ben handling the whole Daddy thing?" Tristan spoke up once he walked back into the living room. I smiled down at Parker.

"He's doing okay. Although, I think it's going to be a problem for him if we have a girl. He's always talking about teaching Jamie to play sports among other things." Tristan chuckled, sitting down.

"Jamie?" He questioned.

"Parker James." I responded, to which Tristan nodded too.

"And how is teaching all those delinquents going for you?" Nicky had started tugging on his shirt as he spoke, interrupting whatever he had been about to add.

"Pretty great. I had one of the girls come up and thank me for helping her get back on her feet. I mean, it's only one girl out of fifty, but it still means a lot to know I'm making a difference." Parker started whimpering as I smiled across the room at Tristan.

"That's why I love you, Sydney. You're an amazing person." I thanked him with a nod and picked Parker up, smiling down at him. His big blue eyes were glistening with tears as he tugged at the hem of my shirt.

"Don't cry." I whispered to him, kissing his forehead, "I brought Bunny with me." I grabbed his stuffed rabbit from the baby bag and held it in front of him.

"Oh my God, Sydney! I'm so sorry, I thought you wouldn't be here until six!" Jessica threw her hair into a bun as she made her way over and pulled me into a hug. "You look amazing! I wish I looked as great as you did after I had Nicky." Her son had climbed on to her lap and was hugging her as she laughed and kissed the top of his head.

"Bennett's been making us walk at six like every morning. He says it's a good work out. I just think he's doing it because he feels guilty for eating so much junk from the bakery." Everyone in the room laughed until Jess broke it and started clapping.

"So what are you doing with the wedding? Are you going to have 'From Mr. Pessimist and Ms. Optimist to Mr. and Mrs. Banks' written across all the banners?" I giggled, still waving Bunny in front of Parker.

"Yeah, and we'll send out sticky notes for invites." I responded, but this actually seemed to be a good idea to Jess.

"That would be perfect. And then we could-"

"Jessica, sweetie." Tristan whispered, "You don't want to overwhelm the poor woman." She shot a look in her boyfriend's direction before turning back to me with a smaller smile.

"It's going to be great." She said, fanning herself dramatically. Nicky started fanning her too, laughing.

"You're right." I answered with a grin, "It's going to be perfect."

*

I groaned as I slid into the bed beside Bennett, hesitating for a minute to make sure I'd turned the baby monitor on.

"You look exhausted." He pointed out, setting down the checkbook in his hands.

"You try spending two hours at Tristan and Jess' place while she goes on and on about different wedding ideas and starts teaching me how to walk a certain way down the isle. Ben, I think she's as excited about this as we are." He made a sound as he stretched his arms over his head, yawning.

"Was Jamie fussy again?" He asked.

"A little. He stayed pretty occupied with Bunny for a while. How's Erin doing?" I watched the light in his eyes dim a little.

"She's doing okay. She wants to come stay with us for a while, like split custody, but her grandparents won't let her. She's threatening to run away from them." I stared at him, frowning.

"That's not good."

"Not at all." He ran a hand through his hair, making it messy, "I told her to just call if she wanted to come over. But she's mad at me too, for not fighting more for the shared custody." I reached over and rubbed his arm, shaking my head.

"It'll work out, Bennett. Everything will work itself out." He leaned over me and turned the lamp on my side off, letting me snuggle up against him and lay my head on his chest as he went through the checkbook in his hands, his glasses sliding down the bridge of is nose.

"You look like a sexy professor." I said, pushing his glasses back up. He leaned down, chuckling.

"Oh, yeah? Because the last time I checked you were the only hot teacher here." I kissed him and watched as he scribbled something down and yawned again.

"You remember all those sticky notes you wrote me seven years ago?" He asked.

"Of course."

"Well, I let Erin take them and she's making some sort of collage for your birthday." I smiled, sighing.

"Thanks for telling me the surprise, babe." I said sarcastically. He turned the light out and wrapped his arms around me, burying his face in my hair, one of his hands tracing along my back.

"Don't worry, Syd. There are plenty other surprises too." I laced my fingers through his, shutting my eyes.

"Goodnight, Sydney." He whispered softly. I squeezed his hand a fought the urge to laugh at my response.

"Goodnight, Mr. Pessimist."


***AN***

There it is, guys. The end. I'm crying right now, so please excuse me. . .

I really hope you guys enjoyed reading this as much as I enjoyed writing it! 

Thank you all for taking the journey with me!

~ChasingMadness24

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