Almost Stepbrother

I am currently trying to force a third pair of thigh-high boots into a suitcase that is already begging for mercy.

“You’re going to the Oregon wilderness not Paris Fashion Week,” my best friend Riley says from my couch. She is swirling a glass of Pinot Noir with the kind of relaxed elegance I currently lack with her legs curled under her on my thrifted velvet sofa.

“First of all, it’s a family resort. There will be formal dinners,” I say, leaning my entire body weight onto the hard shell of the Samsonite. The zipper groans in protest. “Second of all, a woman needs options. What if I meet a handsome park ranger who wants to discuss forestry over a candlelit dinner? I can’t do that in hiking boots.”

“You hate hiking.”

“Exactly. Which is why the outfits need to do the heavy lifting.” I wipe a stray strand of dark hair from my forehead and glare at the bulging box.

Riley watches me for a moment before she says, “So… are you going to tell me what actually happened, or are we just going to pretend you’re packing three weeks’ worth of clothes for a fourteen-day trip because of the ‘weather’?”

“I told you… we broke up and it was mutual.”

“Bullshit,” Riley says. “Nothing is ever truly mutual after six months. Someone always gets the short end of the stick. Who initiated it?”

I let out a long breath, abandoning the suitcase for a moment to slide onto the barstool across from her. The studio apartment is small enough that my kitchen island is basically an extension of my living room, which makes interrogations like this entirely unavoidable. I reach for the bottle and pour myself a generous glass.

“Fine,” I admit, looking at my glass. “It was mostly me. But I let Marcus believe it was his idea. It’s better for his ego that way.”

Riley scoffs. “You did the classic slow-fade exit strategy, didn’t you? Why though?? Marcus is gorgeous. He has a great job, he’s polite, and he actually remembered your birthday.”

“Remembering a birthday is the bare minimum not a personality trait,” I say, rolling my eyes. “And yes, on paper, he’s perfect. He’s stable. He’s respectable. He wears cashmere sweaters and knows how to invest in a 401k.”

“But?”

“But the spark wasn’t just gone, Riley. It never actually arrived. It was like trying to start a fire with wet matches.” I lean forward, resting my elbows on the counter. “The man fucked like he was filling out a freaking spreadsheet. It was incredibly organized, highly efficient, and entirely devoid of any actual excitement. Every Tuesday and Friday, right on schedule. The same three positions. In the exact same order.”

Riley’s eyes widen. “No!”

“Yes,” I say, nodding solemnly. “And God forbid I tried to steer the ship. If I asked for anything different, he’d look at me like I’d just suggested we commit a federal crime. He was entirely selfish, but in that deeply annoying way where he genuinely believed he was a god in the bedroom because he read an article in a magazine once.”

Riley bursts out laughing, throwing her head back against the cushions. “Oh… you poor thing.”

“Exactly.”

“It's kinda your thing, you know…” Riley says after her laughter dies down. “You pick these incredibly safe, predictable men who look great on a resume but give you absolutely nothing to work with emotionally or physically. You’re a serial monogamist. You jump from one safe harbor to the next because you’re terrified of open water.”

I look down at my glass. “Safe is good. Safe means no surprises.”

“Safe means you’re bored in your twenties,” Riley counters gently. “When was the last time you actually felt something real with someone? Not just ‘he’s a nice guy.’ I mean when was the last time someone actually made your heart race?”

I don’t answer. The truth is, the emotional numbness isn’t just about Marcus, or the guy before him. It’s been four years since a police officer told me that my brilliant larger-than-life father wouldn’t be coming home because a drunk driver didn’t see his sedan at the intersection.

Ever since that night, my world has been about risk mitigation. If I keep everything controlled, if I choose the boring, predictable path, then nothing can catch me off guard again. Nothing can break me like that again.

Riley notices the change in my posture and the humor leaves her face. “Hey. I’m sorry. That was insensitive. I know you’re still dealing with everything with your dad.”

“It’s fine,” I say quickly, offering a tight smile to dismiss the heavy air. “Really. It’s just… the anniversary is coming up next month and going up to the very resort he always spoke about visiting… it brings up a lot. My Mom, sisters and I are gonna be cooked up in the same house for two weeks and hopefully not murder each other.”

“Which is exactly why you need to shake things up a lil,” Riley says, her eyes suddenly lighting up with the mischievous look I know too well. “You need a circuit breaker. Something to shock your system back to life.”

“I do have a circuit breaker. It’s called a vacation.”

“No, a vacation is just you overthinking in a different zip code,” Riley says, sitting up straight. She sets her wine glass down on the coffee table with a decisive click. “I’m issuing a formal dare.”

I raise an eyebrow, amused despite myself. “A dare? What are we, twelve?”

She ignores me. “During this pristine, lakeside family vacation, you are required to have one random, completely detached hookup with a hot stranger.”

I immediately choke on my wine, coughing as the liquid burns the back of my throat. I thump my chest, staring at her like she’s lost her mind. “A random hookup? At a family resort? Riley, my mother will be within a five-mile radius at all times.”

“Then don’t get caught,” Riley says, a wicked grin spreading across her face. “No strings attached. No resume checking. No asking about his 401k or his long-term career goals. Just find a gorgeous guy, let him make you forget your own name for a night, and walk away. A pure, unadulterated rebound to clear the palate.”

“I’m a cautious, responsible adult,” I say, leaning back against the counter and shaking my head. “I don’t do casual encounters with strangers in the woods. That’s how horror movies start.”

“Oh, come on. Where’s that competitive streak I know Ava Kingston for?” Riley leans forward, resting her chin on her hands. “Fine. Let’s add some flavor to it... If you go through the whole two weeks and don’t do it, you have to pay for our entire weekend trip to Vegas this fall. Flights, hotel, drinks, everything.”

“And if I do?”

“Then I pay for Vegas. Every single dime.”

I look at her, my mind immediately calculating the costs. A fully paid trip to Vegas is no joke, but the alternative requires me to entirely abandon my comfort zone.

Still, I feel a strange unfamiliar flicker of intrigue in my chest. When was the last time I did something entirely for myself, without calculating the long-term consequences?

Still…

“There aren’t going to be any hot strangers in the Oregon woods, Riley,” I say, trying to sound dismissive, though my pulse is quickening. “It’s going to be families, retirees, and guys in flannel who think a romantic evening involves talking about their favorite chainsaw. I’m not into the rugged lumberjack type.”

“Then you have nothing to lose by taking the bet,” Riley says with a shrug. She extends her hand across the kitchen island. “Unless you’re scared.”

I look at her hand, then down at my half-packed suitcase, and finally back to her face. The caution that usually rules my life screams at me to laugh it off and pour more wine. But the numbness and the suffocating boredom of the last six months, pushes back harder.

I reach out and clasp her hand, a slow, wicked smile creeping onto my face.

“Fine,” I say, my heart doing a sudden, nervous flip. “It’s a dare.”