Page 10 of Holiday Situationship

I nod, though my thoughts flash back to Chastity. No amount of time in the morning could change her disposition if she was intent on finding fault. I shake off the thought, focusing on the present and getting into some real clothes before anyone else exits the kitchen.

“I was just going to change and go for a quick run,” I whisper, thankful the cool air has helped with my morning wood.

Ryan eyes me skeptically, his eyes drifting to the snowy, frost covered window. “In this weather? The driveway’s rocky and slick. You sure that’s a good idea?”

I follow his gaze to the snow-covered landscape and the winding, treacherous path leading up to the retreat. He’s right, of course. Running in these conditions isn’t just impractical; it’s downright dangerous. I need another plan.

Ryan takes a sip of his coffee, then nods towards the fireplace, where a few logs are burning low. “I was about to head out for more firewood. Why don’t you join me? You can work off some of that energy, and we’ll double our efforts.”

I hesitate for a moment, considering the option. It’s not the escape I had in mind, but it’s something. Plus, it gives me a reason to be out of the bedroom without raising too many questions.

“Sure, that sounds good,” I say, forcing a smile.

I change quickly in the downstairs half bath and meet Ryan at the front door.

As we step outside, the cold air hits me like a slap in the face, instantly cooling any lingering warmth from holding Annie in the night. I dig a pair of gloves from my coat pockets, and Ryan and I head to the woodpile. I take a deep breath and allow the crisp air to clear my mind as we trudge through the snow crunching underfoot.

“Nothing like a bit of hard work to clear the mind,” Ryan says, glancing at me.

I nod, grateful for the distraction. “Yeah, I could use that right now.”

As we load the firewood onto the sled, my mind circles back to what happened upstairs. The almost-kiss, the way Annie looked at me—confused, surprised, maybe even a little scared. I grit my teeth, feeling a pang of guilt. I’ve tried so hard to show her that I’m interested in more than just friendship, that this trip could be our second chance. But what if I pushed too hard, too fast? What if I’ve already ruined everything by spooking her?

I’m terrified of losing what we already have, but I want so much more. She means everything to me, and the last thing I want is to risk our friendship by making her uncomfortable or, worse, pushing her away. But the thought of spending this entire week pretending to be her boyfriend, only to go back to being “just friends” afterward, is something I can’t stomach.

I need advice, but asking Ryan feels risky. He and Julia think we’re already a couple. If I say too much, I could blow our cover and make things even more complicated. But he’s been married for years, knows what it takes to make a relationship work, and maybe—just maybe—he can offer some insight without me having to spill all the details.

“Can I ask you something? It’s, uh, kind of personal.” I keep my tone casual as I brush snow off my gloves.

Ryan straightens from a stooped position with a hand on his lower back. He gives me a curious, unfiltered look. “Sure. What’s on your mind?”

I hesitate, trying to find the right words. “You and Julia—you’ve been together for a long time, right? Like, how did you know she was the one?”

Ryan’s expression softens, years of experience reflected in his eyes, as if he’s seen and lived through the complexities of love and relationships.

“There was never a doubt in my mind with Julia. I’d been in countless relationships before I met her. They were all wild and fun, but once the newness wore off, there wasn’t anything left. They were just women I dated, not even friends.” he says, leaning against the wood pile. “But when Julia came along, I knew in my gut she was it for me. The trick was figuring out how to show her I was the one for her, too, without knocking her over the head and dragging her back to my man cave like a goon.”

Ryan chuckles and grabs another log from the pile. I consider his words, feeling the same sentiment about Annie. I think I’ve loved her from the first time I saw her. We had an instant connection, like we clicked from the start. But being so young, we cemented our relationship in friendship.

“Yeah, that makes sense.” I rub the back of my neck, carefully choosing my words so Ryan doesn’t suspect the truth about Annie and me. “I’ve never been great at transitioning from friendship to something more,” I admit, keeping my tone light, though the reality weighs heavily on me.

Ryan gives me a measured look, his eyes narrowing slightly as he studies me. “But you’ve got Annie,” he says, his voice taking on a more serious tone. “If something’s on your mind, you’re in good company here. If you’re looking for the right moment to take that next step with her, Julia and I are happy to help.”

His words sink in, and I realize he’s misreading my hesitation. I’m not looking to propose, I’m struggling with how to let Annie know I want more with her without spooking her and making a fool of myself like I did this morning. But the irony of his suggestion isn’t lost on me—Ryan’s advice might be exactly what I need, just not in the way he thinks.

“Yeah,” I say, nodding slowly, appreciating the advice but still feeling the weight of the situation. “But what if things have been a certain way for so long, you don’t know how to change them? Like, what if you’re stuck in this... situationship where things are comfortable, but you know there could be more?”

“That’s a little trickier, no doubt about it.” Ryan chuckles softly, but his expression turns thoughtful. “But if you care about her, and you’re sure she’s what you want, you have to take a risk. It’s scary, but it’s worth it if she feels the same way. And if you’re not sure—well, that’s where being honest comes in.”

I swallow hard, knowing that honesty is exactly what I’ve been avoiding with Annie. “But what if it’s more complicated than that?” I ask, trying to keep my voice steady. “What if there’s something at stake that could mess things up, like work or mutual friends?”

“That’s when you have to weigh what’s more important—staying safe in the situation you’re in or taking a chance on something better.” Ryan tilts his head, considering my words. “No one said love is easy, but if Annie means that much to you, you’ll figure it out. And if she is the one, she’ll be willing to take that chance with you.”

His words hit home, and I feel a little more grounded, though the uncertainty still lingers. Talking to Ryan was the right move. It’s clear he’s not going to pry into the specifics, and I’m grateful for that. Now, I just need to figure out how to take the next step with Annie without making a mess of everything. Like the man said, that starts with honesty.

CHAPTER 7

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