Dear Mr. Pessimist,

Have you ever had something that was so much easier to write down on paper then say in person? I like you, Ben-

xoxox

I stared at the sticky note, shaking my head to myself.

What the hell is wrong with me? I'm not even that sure my feelings are romantic for him. I shouldn't be sitting here and leading him on, if in some alternate universe, he were to like me back.

"You've always been honest with guys." Jessie said from where she was spinning around in my computer chair, "What's so different about Bennett?" I shut the sticky note in my book and sighed.

"I don't know. I just. . . I don't want to hurt him, to see him hurt anymore. I feel like. . . like-"

"Like it's your fault every time he gets pissed off? Like you do everything you possibly can but it's still not good enough for him?" She went on, shoving a spoon of chocolate chip cookie dough ice cream into her mouth.

"Yeah." I replied.

"Sydney, my dear, I think you like Bennett a lot more than you think." She pointed the spoon at me, "and I think you feel so strange about it all because you're used to helping guys with no strings attached. For you it's always been about proving how good they really are and trying to make them see the good in everything. But with Bennett, you feel like you can relate to him. You've let your guard down and now all your emotions are whirling around inside you." I stared at her, letting what she said sink in.

"You're still studying psychology?" I guessed, trying to divert the subject for a moment.

"Yep. Now stop trying to get around it, Syd. I'm your best friend, now spill." I sighed, rubbing the side of my head.

"I don't know what the hell is going on with me. I didn't feel anything before the other night. I mean, I felt like we were friends, which was already a step forward, but he hugged me and I felt like I wanted to stay in his arms all night." I explained.

"Go on." Jessie said, making a gesture with her spoon.

"And at work he. . . he won't take the job my dad is offering him even though it's perfect. He said he doesn't want hurt me by taking it. And then he had the cute little lip curl that always turns into a half smile." I heard Jessie giggle before I saw her face light up.

"You know that psychologist aren't supposed to laugh at their patients." I pointed out, smirking.

"Okay, okay. I'm good, now go on." She crossed her legs on the chair and propped her head up on her hands.

"A couple weeks ago, after work and after that party, we were walking in the park and he kissed me. He started to-"

"Oh my God, he kissed you? Sydney! That's. . . okay, sorry. You've got to remember I'm seventeen and you're my best friend." She shut her eyes and took a deep breath before smiling and nodding for me to go on.

"He started to pull away, saying he was sorry. And I kind of, well, I said that he needed to figure out his feelings before he pulls me down with him. But I think I like him, Jess. When he kissed me, I wasn't that sure. But the other night, on my porch, I realized it." She nodded, her eyes searching mine for a second before she spoke up.

"Do you like him more then you liked Zey?" She questioned.

"I never liked Zey, Jessie. I liked the idea of him."

"Okay. So I'll take that as a yes." She whispered, "Now do you want me to respond to this as a psychologist or a best friend?" I frowned, hugging my throw pillow against my chest.

"Both?" I tried, hoping she could give me her opinion in both ways.

"As your best friend, I think you should be careful, Sydney. You're like one of the sweetest, bravest, kindest, most amazing people I know. I don't want to see someone take that away from you. But Bennett seems like he might return the feelings, so I suggest maybe you should try to talk to him subtly about it." I nodded.

"As a psychologist, I believe from what you've been describing that both of you are uncertain of your feelings. Bennett's. . . well, he's obviously been through a lot and has trust issues. Just the fact that he has started to trust you is a great sign. I think you should both try and find a way to speak about it, a way where you both don't have a fear of being rejected." She finished, smiling sadly.

"I love you, Jess." I responded, smiling as she plopped down on the bed beside me and laid her head on my shoulder.

"I know, Syd. And I'll be here too support you through it all, don't forget that."

*

I ended up walking into Doughboy as a customer for the first time all summer. I was shocked to find Bennett talking to some new girl, a new trainee maybe, behind the counter. I had no doubt in my mind that they were flirting.

"Syd, hey!" Tristan popped up out of no where, grinning.

"Sydney, this is my sister Abbey." Tristan made a gesture toward the girl beside him, "Ab, this is the girl I was telling you about, Sydney." I walked up and took her outstretched hand with a smile.

"Hi." I said.

"I've heard so much about you! I feel like we've already met." She joked, laughing. Bennett cracked a smile, sending me a welcoming nod.

"You don't have to work today, so what are you doing here?" Tristan asked, earning a dirty look from his sister.

"Nice way to make a girl feel loved, Tristan." I replied, "I wanted to come as a customer for once, if that's okay." He snorted.

"Cool, you might as well take a seat before the lunch rush." I nodded and walked over to a booth, dropping my purse beside me.

I looked back up to find Bennett and Abbey talking again, a full smile spreading across Bennett's face.

"Don't look at them, they'll think you're jealous." Tristan whispered in my ear, setting down a plate of cookies in front of me before sliding into the booth across from mine.

"He's smiling." I said, nodding toward them.

"Of course he is. My sister has some magical power that makes everyone love her. You guys actually kind of remind me of each other." He took a cookie, glancing over his shoulder as the couple behind the counter laughed.

"I don't see him smiling like that very often." I went on. Tristan raised an eyebrow.

"Then you must not see him when we're talking about you after work. He likes you, Syd. And you don't have to worry about Abbey, she's engaged and the guy is like this monster that could crush us all." I laughed, picking up a cookie and staring at it.

"She's also almost thirty and finds Bennett kind of kiddish because of his attitude. I'm not saying you are jealous, I'm just letting you know why you shouldn't be." He shut his mouth as Bennett made his way over to us and stole a cookie from the plate.

"But we all know you are." Tristan said, a smirk playing on his lips as he slipped passed Bennett and toward his older sister.

"Hey." He said, sitting down where his best friend had just been.

"Hey." I waved a little.

"So Tristan made you cookies, hmm?" He said, his lips curling up into a half smile. I felt my hand twitch at my side as I laughed nervously, remembering my conversation with Jessie this morning.

"Oh no, that's not my cookie, or cookies for that matter. I think he made them for himself and just wanted to share them with me so he didn't feel so bad for eating them all." We both laughed. I tucked a strand of my hair behind my ear and was about to speak up when he did first.

"My family is throwing this reunion thing this weekend, and I was wondering if you wanted to come with me?" He asked, his eyes roaming my face as if it would give something away.

"You want me to pretend to be your girlfriend again?" I whispered, not knowing exactly how to feel about it.

"What? No, no. I just wanted to know if you wanted to come and hang out, as friends. Because obviously I don't have a lot of them." He said quickly, his eyes darting in the other direction, "You don't have to, if you're busy I can just-"

"Of course I'll come, Bennett. I'd love to meet your family, it'd be fun." I swear I heard him sigh in relief.

"Great. So we can plan when I pick you up and everything tomorrow or something." I nodded, leaning back in the booth and returning his lopsided smile.

"Okay, sounds good to me." He started to walk away, but paused and pulled something out of his pocket and laid it down on the table in front of me. I waited until he was back in the kitchen to unfold the sheet of line paper and read what it said.

Dear Ms. Optimist,

How do I even begin this? It's so much harder then you make it look. I wish I could say everything you do, but I can barely even spell my name here. Can you tell me what you wished for on the shooting star? I know that means it won't come true, but I want to know.

Some people thought I was an ass because I'm rich, because I have parent issues. But is that the truth? Look at you, the daughter of one of the richest men in America, and you are everything that breaks that stereotype.

The point of this thing, which obviously I can't do right, is to tell you the reasons I believe you should love yourself and the world.

You showed me this last month and half what it's like to have a friend again, to trust someone with my everything.

I love how blunt you are. You aren't afraid to go out and speak whatever it is that's on your mind. I like the way your green eyes start to glisten whenever you're happy. You make everyone around you genuinely happy, even when you feel broken yourself.

Am I stupid for writing this? Maybe. I just couldn't say this out loud. It seems no matter how hard I try to say whatever it is on my mind, it turns out to be wrong in someone's eyes.

So tell me, Sydney, tell me why I think about you so much? Why I wish that you would just leave my mind and go back to just being the annoyingly optimistic girl you were when you first started working here? Why'd you have to get under my skin, break down my walls?

I thought I loved Hannah, that my world revolved around her. But maybe. . . maybe it wasn't quite love, maybe it was infatuation.

Thank you, Sydney. For being here, for actually standing by my side the last couple months. The only way I thought I could get through to you properly was by using your own little game.

Smile, Sydney, please.

Yours truly,

Mr. Pessimist

I grabbed a pen and sticky note from my purse and started to respond to his first question without hesitation. I slipped his note into my purse with a smile, grabbing the sticky note and heading toward Bennett as he walked out of the kitchen. I slapped the sticky note against his jacket before taking my items from Tristan and heading for the front door, reciting what I wrote on the note in my head.

Dear Mr. Pessimist,

I wished for you to be happy again.

With love,

Syd

p.s Thank you for changing my life

***AN***

I hope you guys enjoyed! 

Let me know what you thought about Bennett's letter!

Love you <3

~ChasingMadness24