Enemies With Benefits

EWB 33

Hailey

Caseyyy: hey, is it cool if we bring Caleb?

I looked at that text over and over again.

It has been a week since I last saw Caleb.

All throughout the week, I did everything I can to get up extra early so I wouldn't have to bump into him when I get my morning coffee, since he was always there everyday and there wasn't any other good coffee places that I could go to.

Things with my classes were getting busier too, anyways, so waking up earlier than usual and heading to the library to do some quick studying was working well for me.

Not to mention, me and my friends found a place to do our all nighters, so we haven't been to Jake's apartment in a while.

But just when I thought that I was doing such an amazing job at avoiding the plague, my best friend asks me if her brother can come.

I didn't have a problem with it, to be honest. I get she's going through something and she also misses her brother.

The only problem I have with it is the fact that I'm not sure Dean would be comfortable with the fact that Caleb was in the same city as me, let alone hang out with him.

I never told him about how I spent the night at Caleb's last weekend, and I sure as hell don't wanna lie to Dean about this one too, so I left Casey on delivered first before saying anything.

By 7pm, my phone rang, signaling Dean's daily call when he gets home.

"Hey baby" I answered with a full smile on my face

"Hey, I was just thinking about you" he tells me as I roll my eyes playfully

"Aren't you always?" I answer, making him laugh

"Yeah" he says "Anyway, aren't you supposed to be getting ready for your night out with Casey?" Dean added, making me feel more anxious. So I took a deep breath to prepare myself.

"Yeah, about that..." I began as Dean looked at me with a worried look on his face

"What, did something happen?" he asks

"No, nothing" I tell him as I ready myself to tell him all about it "Just... apparently, Caleb is here"

Dean blinked for a couple of seconds before he answered

"What, like, with Casey?" he asked

"Like..." I said "He lives in here too" I added, making Dean silent for a bit as he leans back in his chair.

You know what the scary, frustrating part about this though? It was the fact that Dean didn't look mad about finding out that Caleb was here.

It was the fact that he had a neutral reaction, which honestly scared the shit out of me, and I wasn't even doing anything wrong.

"Okay?" he just answered like normal

"Casey was asking if Caleb could come, and I wanted to ask you about it first" I told Dean, but it didn't do anything to change his face

"I mean, I trust you" Dean said "And I get Casey must've missed her brother too"

"Yeah. I can always tell Casey 'no' though. I don't want you to be uncomfortable" I told Dean, which made him kinda smirk as he looked at me amused

"I'm not worried about me baby, wouldn't you be the one uncomfortable about it though?" Dean asked.

And I know Dean was saying something, but all I could think about was how he sounded like he was trying to reverse psychology things on me.