Page 10 of Accidentally Falling For My Best Friend (Chicago Awakenings #2)

I was lucky enough to grow up with not only my own incredibly supportive parents, but also with the whole Caldwell family treating me like one of their own.

As a straight man, I’ve never had to question if anyone would treat me differently because of who I was dating, but I know without question that the people in my life love me unconditionally, not because I fit some standard they’ve set for me.

Aspen scoffs. “Yup. My father is a politician in a very conservative state. There’s also millions of dollars I’ll lose access to if I don’t marry a man soon,” she confirms. “I’ve just never been attracted to men, I’ve tried to make something work with boyfriends in the past for my parent’s sake, but I’m not built for that.

My parents have been trying to get me to move back to Georgia for years to marry their friends’ son. ”

“That’s horrible,” I blurt out, completely unsure how to react to all of that. It really is an awful situation to be in, and I feel sorry for her, but I’m also confused why she’s sharing all of this with me. Maybe she just needed to tell someone?

“I know,” she says sadly. “His dad is my father’s campaign manager, and they’ve always wanted him to take over when my father retires.

They’ve been trying to set me up with him since we were kids.

It started as more subtle suggestions about how great he is, that we would be good together.

He’s a great guy, we’re still friends, but now that I’m almost thirty it’s like they think I’m an old spinster now and they’re relentless.

They’ve been threatening to cut off my access to my trust fund if I don’t move home soon, saying the money is intended for my family and that I shouldn’t be able to use it until I have a husband and children of my own. ”

“I’m so sorry you have to deal with that,” I tell her honestly.

“ Thanks, Parker. And the worst part is my father helped me start my company, so he’s stuck in my life.

I’d forget the family money in a second, but my business is my baby, I don’t want to risk him sabotaging it.

” She hugs the pillow in her lap tighter to herself before letting out a defeated laugh.

“I was actually hoping you’d be able to help me out, but I guess I was convincing myself that you had feelings for Oakley to try to justify what I wanted you to do.

” She shakes her head a few times before muttering, “It was a stupid idea anyway.”

“What was?” I can’t help myself from asking.

“Well, I thought that maybe, if you were in the same position as me, doomed to pine after your best friend while watching them fall for someone else, that you wouldn’t mind dating me, or pretending to at least,” she explains quickly.

My jaw drops and I can’t help but gape at her. That is not what I was expecting. “Why would you want to pretend to date me?”

“Mostly to get my parents off my back,” she huffs out.

“They want me to move back there, and they keep going on about how ‘it's clear I can’t find a husband in Chicago.’ But, if I were dating a successful, wealthy man like you, then they would have to shut up about it, and I could at least buy myself some more time here.”

“Like a beard?” I don’t know if that’s even what it’s called, and that’s so not the point, focus.

Whatever it’s called, it does sound like it would help her out with her family.

I wouldn’t feel guilty about lying to them if they’re such awful people.

They’re in another state, how would they know who she’s dating anyway?

We wouldn’t actually have to be dating for them to think we are.

“It’s also been referred to as a lavender relationship. I thought it would be perfect that we’d be able to keep going on double dates and spending time with our best friends instead of competing for their time with their new relationship,” she adds with a shrug.

Now that really gets my attention.

That’s exactly what I was going on about in my daydreams of a relationship with her earlier tonight. How great it would be to get to still spend so much time with Oakley, despite the fact that he was dating someone.

I didn’t really care about the possibility of having a new girlfriend myself, I was more focused on how my friendship with Oakley would be affected.

There’s no denying the four of us all hanging out together was fun.

Aspen and I definitely get along. We didn’t even kiss, but more nights like tonight don’t sound bad at all.

I only agreed to ask her out in the first place because Oak suggested it, it’s not like I was the one eagerly seeking a girlfriend.

Even the thought of hooking up with her hadn’t really been on my mind until I was worried about her expectations.

Sure, I enjoy the release from sex when it happens, but I’ve never been as sex-focused as other guys seem to be.

The more that I think about it, the more the idea of agreeing to “fake date” Aspen sounds like a decent plan.

At least while Oakley is seeing Sage. There would be a clear expectation of no physical intimacy between us, so I wouldn’t have to waste any time wondering what she wanted from me.

Dating always brings me back to feeling like the new kid, second guessing what people think of me, worrying if I’m letting them down by not behaving how they hoped I would.

I usually wait for the woman I’m with to take the lead when we’re alone so that I know I’m not making a fool of myself.

This could work. We could call it dating each other, and we’d get to keep going on double dates with the people we actually want to spend time with, without me having to stress about messing up the physical expectations that come with most relationships I’ve never seemed to understand.

It sounds way better than sitting at home by myself whenever Oakley wants to spend time with Sage.

Just because I’m not in love with Oak like Aspen was hoping, doesn’t mean I wouldn’t still benefit from her plan…

“I’ll do it,” I blurt out before I can overthink and talk myself out of it.

Aspen tilts her head, arching a brow, clearly confused. “Do what?”

“I’ll be your pretend boyfriend. We can keep spending time with Oak and Sage, and you can get your parents to give you space to stay in Chicago and figure out a more long-term plan.”

Her whole face lights up and she scrambles so that she’s kneeling on the bed now, bouncing slightly in her excitement. “Really? You’d do that?”

“I’m not going to agree to marry you or anything, but at least while Oak is dating Sage, I don’t see why we can’t all spend that time hanging out together,” I offer.

Aspen is somehow off of the bed and jumping into my lap before I even know what’s happening.

She wraps her arms around me in a hug, squeezing tightly.

Even in this position, with her practically straddling me, I’m not disappointed that our relationship won’t be physical.

Maybe there’s something wrong with me, but I just can’t find it in myself to care right now.

I’m glad I can help her and, from the little I know, I do think we could be good friends.

And I don’t have to give up any of my time with Oakley.

“So, do you want to go home, or spend the night here? We can watch TV or I have a lot of puzzle books if you do want to stay,” I offer.

“You don’t mind if I sleep here with you?”

“No. Oak and I used to share a bed all the time. I don’t think it would be weird, if you’re okay with it.”

Aspen gives me a questioning look, like she wants to comment on that statement, but decides against it. “That would be great. I’m sure Sage will be staying,” she says with another pointed look at our shared wall where things have finally quieted down.

“We can see what they say in the morning as far as seeing each other again.”

“Want to watch that new blind dating reality show for a bit before we sleep?” she suggests.

“Where that guy thinks he’s talking to a girl, but it’s a man?” I check.

“Yeah, the commercials look so funny.”

“Sure, let’s get ready for bed first though.

” I head to my ensuite, finding an extra toothbrush and some of my clothes that Aspen can sleep in before we settle into bed and pull up Love Without Labels on the TV.

My king-sized bed is plenty big enough for us both to have our own space, and there’s zero tension.

It feels like I’m hanging out with Oakley’s siblings.

I grab the constrained cube from my nightstand to keep my hands busy while we watch.

It’s one of the more difficult spin-offs of the Rubik’s cube that Oakley’s gotten for me over the years.

After a few episodes, we’re both drifting off, so we turn off the show and the lights, going to bed with simple, “goodnights.” Maybe the situation should feel strange and I should be more worried about exactly what I’ve agreed to, but I feel a sense of calm about it in a way that I’m embracing.

In the morning over breakfast at our dining room table, Oakley asks Sage when she’s free for their next date. I look to Aspen, who gives me an encouraging nod before I suggest we all plan something together again.

Oakley lights up even more at that, and I know he’s thinking the same things I was last night.

How nice it will be to go on like this, that we might have each finally found someone who could accept our friendship without having to constantly justify our bond.

I should probably feel guilty about hiding this from my best friend, but what Aspen and I have agreed to doesn’t feel like I’m lying to him.

We will be going on dates, we just won’t be having sex with each other.

Despite us normally talking about everything, I don’t bother to share the details of my hookups with Oakley. There’s never really been much to tell.

Something about this feels right, like I’m on the path that I should be. So, I’m going to try not to get hung up on what I think I should be feeling, and just focus on the positives of the situation. I’m helping my new friend, and I won’t lose my time with Oak to his new girlfriend.