Page 7 of Accidentally Falling For My Best Friend (Chicago Awakenings #2)

OAKLEY

THIRTY YEARS OLD

April

“ Y our insulin is ready for pickup at the pharmacy,” I tell Parker as he adds pre-workout powder to his water bottle.

“Thanks, Dad,” he replies sarcastically.

“That’s Daddy to you,” I say with a wink, slapping his ass as he walks past me to our front hall closet to grab his shoes.

He doesn’t react, which makes me laugh. I ignore the way my dick twitches at the contact. It’s been way too long since I hooked up with anyone. I seriously need to find a girlfriend.

“Oak, are you coming?” Parker calls out from our entryway.

I wish I was coming. Fuck, I need to get my mind out of the gutter. “Yup, one sec,” I answer back, grabbing my own workout drink and meeting him to head downstairs to the gym.

We live in the penthouse of one of the newest high-rises in downtown Chicago, and one of the reasons we picked it was for the top-of-the-line fitness center that takes up the entire fifth floor of the building.

It’s also only a block away from my older brother, Beckett’s, building.

We try to see him and his friends as much as we can, and even debated buying there, but it wasn’t as modern as Parker and I prefer.

Some people think it’s weird that Parker and I choose to share a condo when we’re thirty, successful, and have plenty of money for our own places, but I can’t imagine us not living together at this point.

It comforts me to know that he isn’t alone in case anything happens with his blood sugar.

Not that it ever really does, he’s managed to stay out of the hospital since the scare when he received his diagnosis.

But every time someone suggests we move into our own places, I picture him passed out again, with no one around to know he needs help, and I’m reminded of how much I love living together.

Plus, Parker is the best roommate ever. Why would I want to live by myself?

We make our way to the elevator and down to the gym, starting our routine on the treadmills like we usually do with a quick five-mile jog before we transition to the weight machines.

“Look, those girls are here again,” I point out, nodding in the direction of the women I’m talking about.

They seem to have a similar workout schedule to ours, and we’ve noticed them checking us out and glancing in our direction for a couple of weeks now.

We’ve exchanged polite hellos and smiles, but nothing more.

Which seems stupid considering how hot they are, and how fucking horny I’ve been lately.

“Let’s introduce ourselves after this rep,” I suggest, nudging his shoulder with mine.

“Why?” he questions, like he honestly has no idea why I would want to talk to the beautiful girls who seem to be into us.

I’m constantly amused by the way Parker’s brain seems to differ from my own.

He’s always been more introverted than I am, and sometimes I wonder if he would still be a virgin if I didn’t encourage him to talk to women as much as I have over the years.

“To see if they’re single, and if they are, to ask them out,” I spell out with an indulgent smile, endlessly entertained by how oblivious he can be.

“Oh,” he says, sounding genuinely surprised. “Okay, which one do you want to ask out?”

This isn’t the first time we’ve approached multiple girls together, and Parker always seems happy to let me take the lead and decide who I want to talk to first. He doesn’t seem to have a type.

At well over six feet tall, with broad shoulders and huge muscles, not to mention his unique red hair color and movie star chiseled face, with a jawline sharp enough to cut glass, he’s yet to be turned down by any of the women he does approach.

I look back at the girls who are both smiling and chatting as they do their own routine.

One is blonde and the other brunette, but they’re both average height with fit curvy frames that look great in their workout clothes.

“Honestly, they seem pretty similar. We can figure out if there’s a good match when we talk to them. ”

We finish lifting weights and clean off the equipment before heading toward the girls. When they notice us, they stop what they’re doing and stand up straighter, puffing out their chests, fluttering their lashes and smiling at our approach.

“Before I impress you with my cheesy pick-up line, are you ladies single?” I ask with a smirk.

They both laugh and nod, so I continue. “Are you my next workout? Because my heart is racing, and you’re making it harder for me to breathe,” I say with an exaggerated wink.

Parker snorts beside me, and the girls both let out short laughs.

“I’m Oakley and this is my best friend Parker,” I finally introduce us.

“Nice to meet you,” the blonde girl says with a little flip of her ponytail. “I’m Sage and this is my best friend, Aspen,” she waves to the brunette who’s smiling and holding eye contact with Parker. Looks like I’m asking out Sage.

“ Well, Sage, is there any chance that I could get your number so we could all go out some time?” I ask with my most charming smile.

“Like a double-date?” she clarifies, sounding excited.

It’s been awhile since Parker and I have gotten to do the whole double-date thing, and it sounds like a lot of fun. “If you both would be up for that,” I reply hopefully, glancing at Parker to see if he’d be interested. He gives me a slight nod before aiming his smile back toward Aspen.

“Okay,” both girls say in unison before laughing. We all exchange numbers and I start a group chat so that we can plan something.

“Well, we’ll let you get back to your workout,” Parker says. “It was nice to formally meet you both.”

“Bye, Sage,” I say with another wink, earning a huge grin from her before we return to our own routine, showing off a bit in case they’re watching.

“Are you ready to present to the board?” Parker asks, knocking on my door as I’m scrolling through images of island resorts on my computer. We have a big meeting scheduled with the board of directors today about an idea I’ve been wanting to pitch for a while now.

My dad will be there as the majority shareholder of the Caldwell Hotel brand, along with some of the other executive VPs and board members.

As President and CEO of the brand, I have a lot of independence in my day-to-day work, but this idea isn’t going to be cheap, so I’ll need the board’s approval.

It’s also the first major investment that’s been proposed since Parker took over as CFO a few months ago, and I know some of the board members are concerned about our positions being filled by such “young” men.

I’ve been in my role for a few years now.

After the various jobs I had in Caldwell House throughout high school, I shadowed Parker’s mom, their GM, that first summer while Parker worked with their accountants.

The summer after that, I filled in working as an assistant manager, and Parker shadowed their finance department’s lead.

For our final summer before senior year, we traveled to different hotels within the company.

We saw more moderate options, as well as some of the deluxe resorts that are all over the world, learning about how each hotel operates.

We both did accelerated master’s programs, and by the time we graduated, the previous President and CEO was getting ready to retire. I spent almost a full year studying under him and spending time with each of the executive VPs so that I was prepared to take over when he officially stepped down.

Parker might not have the Caldwell name, but given his vast experience within the company and his track record of excelling in the role below the former CFO, he was the obvious choice to take over when they retired.

The majority of the board agreed with my recommendation, but a few didn’t seem thrilled that we’re such close friends outside of work, questioning if we would be able to focus or keep the best interests of the company in mind if we disagreed about something.

There’s still the occasional shared glance between some of the older members when he and I are both in a meeting, but our friendship has never negatively impacted our performance, so they don’t have anything to legitimately complain about.

“Yeah, let’s go win them over,” I say with a false sense of confidence. I really want this to go well.

We’re not the last to arrive, so I work on setting up my presentation and exchange pleasantries with people as they enter. Once everyone is settled, I take a deep breath and put on my most charming smile.

“Good morning, it’s lovely to see so many of my favorite people all in one room this early in the day. Oh, and Dad, you’re here too,” I say with a wink. A few people chuckle, and I relax just a bit. I’m good at my job, no need to be nervous.

“You’re all aware that we’re here today for me to propose a new investment opportunity for the Caldwell Hotel brand.

I know that all you lot care about is money,” I say in a teasing tone, earning a few more laughs.

“So, I’ll get right to the point. There’s a resort in Bora Bora that’s failed their health and safety inspections, and the family who owns it is looking to sell.

They’ve been doing a lot of patchwork jobs over the years to pass the inspections and the repairs would be extensive,” I admit.

“But, it would still be cheaper than trying to find new land, given the remote location. It’s a smaller resort, and they haven’t offered as many amenities as their neighbors, so it’s fallen out of popularity.

There’s a lot of room for improvement,” I explain.

I’m already getting a few skeptical looks from the board, so I rush to get to the current plan.

“I’m proposing we purchase the existing facilities and do a complete overhaul, turning it into the luxury destination-wedding resort for the rich and famous,” I say with as much enthusiasm as I can while still sounding genuine.

“Obviously, we have other hotels with great wedding venues,” I admit.

“But, I think this could be an exciting investment opportunity to help keep our brand relevant. The wedding industry makes billions of dollars in revenue annually. Statistics from last year show that couples are choosing to invite fewer guests, focusing instead on the quality of their wedding, with extended destination events rising in popularity,” I inform them.

My dad looks interested as I meet his gaze, so I focus my attention on him as I continue.

“I think that this would be a great way to tap into that market in a way that stands out from our other venues.” I pull up pictures of the resort as it currently stands, followed by some inspirational images that my team put together for me.

There’s some appreciative hums from the group, fueling my excitement. They might actually go for it.

Parker gives me an encouraging smile, probably thinking the same thing I am, and I hurry to wrap my part up so he can take over.

“We can hire an in-house events specialist to coordinate the weddings or other large private events, and only offer the resort out to someone booking the entire venue. This will make it more exclusive and spin the smaller size as a benefit. It doesn’t need to only be weddings, but that’s where the majority of our marketing will focus.

If a reality TV star wants to throw a birthday party at our private luxury resort, they can, but they need to book out the whole thing.

We’ll keep the costs lower if we’re catering to the same large group rather than to couples, as most of these resorts do.

Are there any initial questions before Parker goes through the financial projections? ” I ask.

There are a few raised hands, and I answer some general questions about where Bora Bora is, south of Hawaii , how long of a flight it is, eight hours from LA to Tahiti, and another fifty-minute flight to Bora Bora .

There are also questions about the island and the established resorts that are profitable there.

Parker takes over to give the rundown of the initial investment, as well as the projected profits after the first year.

Most of the board members seem interested enough in the proposal, and after about an hour of everyone combing through the materials we’ve provided and asking more questions, the idea passes with a majority vote.

“Thank you all so much for your time today. I look forward to updating you all on our progress,” I say brightly. “If you all would excuse us, Parker and I have another meeting to attend,” I explain as we shake a few hands and wave goodbye before slipping back to my office.

“Fuck yes!” I whisper-shout, doing a happy dance as soon as I make sure we're out of sight. “We’re going to Bora Bora!”

Parker laughs before joining in my silly dance, which I know he only does to amuse me. “It is a good idea, though,” he assures me when we calm down. “Even if it’ll be an expensive one,” he adds a little more hesitantly.

“I know, I’m just really excited about this,” I explain. “You know how much I love weddings, and islands are my favorite. This is going to be such a fun project!”

“Yeah, I think it will be,” he admits with a big smile.

I love making him smile. Working this closely with my best friend and sharing these victories means the world to me.