Fake Dating My Best Friend

1. Isla

Chapter 1

Isla

T oday I’m getting engaged.

At least, I’m pretty sure I will be.

“Hey Asher, the camera’s all set, right?” I whisper, wiping a sweaty palm against my pants and twisting around to check on my best friend. He’s crouched behind one of the festival booths, a wooden setup strung with pastel bunting and cluttered with jars of homemade jam.

The canopy above him sags slightly in the middle, flapping every time the breeze picks up. He looks completely out of place, surrounded by raffle signs and glitter stickers, wearing an expression that reminds me of my aunt’s grumpy cat during bath time.

It’s almost funny. He could scowl all he wants, but with those turquoise blue eyes and that dimpled smile half the town swoons over, it hardly matters. The beloved owner of Collymore Fitness has no shortage of admirers, not that he ever seems to notice.

And of course, I beg my best friend to record the best day of my life because my boyfriend, Kyle, is going to propose.

Who else would I trust? Asher and I have been inseparable since childhood. We grew up as next-door neighbors, always in the same classes, as we are the same age. Even after we moved out of our childhood homes a few years ago, we still somehow ended up as neighbors again.

Asher’s always been my ride-or-die guy, even if he looks like he’s deeply regretting his life choices right now.

“For the millionth time, yes,” he grumbles, adjusting the lens with more force than necessary. “Though I still think this is a bit much. Shouldn’t proposals be, I don’t know, private?”

I fidget with the soft spring scarf, tugging the end through my fingers as I scan the bustling square. The Frosthaven’s Spring Festival is in full swing, the late afternoon sun casting a golden glow over the town square. It’s the town’s biggest celebration to welcome spring, and everyone who’s anyone in Frosthaven is here.

Frosthaven might be a small town in upstate New York, tucked into the foothills of the Adirondacks, but when it comes to celebrating, we don’t mess around.

“Oh please, this is going to be perfect. Kyle’s been acting so weird lately, checking his phone and getting all nervous. Plus, I saw the ring box in his pocket last week.”

I straighten my carefully chosen red scarf. Well, technically, Asher picked it out. I’d sent him three options in a panic because Kyle’s idea of “casual” usually means designer brands and runway-level coordination. Last month, I wore floral boots to his business dinner, and he spent the whole night calling them “interesting.”

I still don’t totally get his high-end style, but I try. Or at least, I try hard enough not to look like the odd one out next to him. And when I can’t figure it out, like always, I turn to Asher.

But at least all the effort’s not for nothing. Kyle’s going to propose.

“He said it was just a keepsake, but come on. Who keeps keepsakes in tiny velvet boxes?”

Asher’s jaw clenches, muscles flexing beneath his perfectly sculpted jawline. “But he couldn’t even remember your coffee order after a year of dating.”

My chest tightens at the sharp edge in his tone, that telltale dip he gets when he’s holding something back.

“He tries, okay?” My stomach does a slow, queasy flip. “My coffee order is complicated. Half the time, I confuse the baristas.”

Asher’s probably the only one who ever gets it right every time. But that’s just because he’s got a freakishly good memory. Most people don’t. Even Elaine and Roxanne, my soul sisters, still mix it up sometimes.

“I saw the ring box, Ash. He’s nervous and acting weird. I know what that means. This time’s different. I’m pretty sure.”

He opens his mouth as if to say something, then shakes his head, returning to fiddle with his camera. “If you say so.”

Kyle and I have been dating for a year now, and everything’s fine. He’s handsome, successful, and he treats me well. And I’ve been trying my best to get this right. Especially with nine failed relationships already behind me. So what if he never remembers my coffee order? Or that mushrooms are basically my sworn enemy? Those are minor things. Right?

“It’s not like I need some grand romantic gesture,” I tug at my scarf again. “I’m twenty-eight, not some starry-eyed teenager.”

Asher never liked any of my ex-boyfriends. And . . . fine. He was right about them. But this time, I’m going to prove him wrong.

A rebellious strand of hair catches my eye, sticking straight up as if it’s taunting me. My fingers fly to my head, desperately smoothing the wayward lock back into place.

“Ash, can you check my lipstick?” I whirl around toward Asher. Maybe the shade is too bold? I scan Asher’s expression, desperate for confirmation. “What if it’s smeared everywhere, and I look like a circus disaster in every single picture?”

“Your lipstick’s fine, Peachie.” A faint smile tugging at his mouth. “And you know what? So are you .”

My traitorous heart does a little flip at his words. Not that I care what Asher thinks about my appearance. Or that he still calls me Peachie, a nickname from the time I nearly knocked myself out climbing his family’s peach tree, convinced the peaches at the top would taste sweeter. And every summer after that, he’d bring me the ripest, sweetest peaches from his family’s orchard. The good ones, Peachie. No concussions required.

Not that I think about that too much. Because that would be weird.

We’re just friends .

With an actual friendship pact that we’d never date each other.

“Did it ever occur to you that maybe—” Asher starts, but the piercing sound of the youth band blasting through the speakers cuts him off.

I wince, the sound cutting through the crisp air like a knife. “Maybe what?” I prompt, but Asher only shakes his head.

“Isla? Is that you?”

I turn to see a woman with perfectly coiffed blonde hair. It’s Bethany Grayson, my current matchmaking client. “Bethany! Hi! How are you?”

Bethany’s eyebrows furrow. Her lips purse into a tight line. She opens her mouth to answer, but the Frosthaven Youth Band launches into another enthusiastic number, their sound amplified through the festival speakers.

Would anyone notice if I snuck over and turned the speakers down just a tiny bit? Well, at least they have a working speaker now. When the youth band’s speaker broke this morning, I offered to grab the spare I keep at my office since everyone else was scrambling. Lugging it over might’ve woken up that same old ache in my shoulder, but seeing their excited faces made it worth it.

Bethany waves a hand dismissively. “Well, let’s see,” she folds her arms. “I’m still single, and I just spent two hours yesterday listening to a guy argue with the waiter about how to pronounce bruschetta .”

My stomach twists. That date. The one I’d marked with three stars in my planner and labeled sure thing. The one I was counting on to prove my updated system was working. It was supposed to make finding the perfect match foolproof.

And I let her down.

“I—I’m so sorry about that,” I stammer, my voice wobbling as the band launches into another high note. “Every match is carefully curated based on—”

“I know your track record. That’s exactly why I signed up,” she leans in, her expression sharp. “Everyone raved about how you have this uncanny ability to understand people and really know what they need.” Her eyes narrow slightly. “But it seems like something’s changed. Every match you’ve set me up with has been a total disaster.”

Okay, ouch. Her words hit me harder than I expected, landing like a snowball to the gut, and trust me, I’m an expert on those after years of losing snowball fights to Asher.

I force a laugh, hoping to mask the hurt in my voice. “I’m really sorry, Bethany. Let me make it up to you. This isn’t how things usually go. Just—just let me have one more shot to get it right, please?”

Bethany’s expression softens and she pats my arm lightly. “Listen, I appreciate you taking this so well,” she says, offering a smile that doesn’t quite reach her eyes. “Take care, Isla.” With a quick wave, she turns and disappears into the festival crowd.

I let out a slow breath, turning back toward Asher with what I hope passes for a convincing “everything’s fine” smile.

Asher leans casually against his camera, his lips twitching into a small smirk, a dimple appearing on his cheek. “You get this little crinkle right here,” he says, tapping between his own eyebrows, “when you’re trying to pretend you’re not two seconds away from losing it. Dead giveaway.”

“You always notice the weirdest things.”

He shrugs. “Not weird if they matter.”

Huh?

“What did you just say?”

“Nothing.”

I search his face, but he’s already back to adjusting the camera.

The band, thankfully, pauses for their intermission, and the square feels slightly less chaotic.

Kyle should be here any second.

I turn back to the festival, determined to push the client’s words out of my mind. This is supposed to be the day of my big proposal, after all.

I scan the bustling festival crowd. And then I see him—Kyle, weaving his way through the sea of people, his dark hair tousled by the wind. But it’s not his windswept look that catches my attention. No, it’s the small, telltale bulge in his coat pocket.

A ring box.

Should I look surprised? Tearful? How will I gush about this moment to my friends later? I can already picture their faces when I show them the ring, their squeals of excitement echoing in my ears.

“Can’t believe I’m recording this,” Asher mutters, his voice barely audible over the din of the festival.

My foot starts tapping involuntarily as I watch Kyle approach. He looks a little distracted, probably nervous about the big moment.

I’m about to wave when another woman approaches Kyle. My hand freezes mid-air. She’s stunning, all long legs and perfect hair, looking like she just stepped out of a winter fashion catalog.

Okay, don’t panic. Maybe it’s a client of his? I try to squash the uneasy feeling in my gut. Or his sister? Cousin? Long-lost childhood friend?

But then she puts her hand on his arm, and he laughs. It’s not the polite chuckle he gives my jokes. No, it’s intimate, the kind of laugh I’ve been trying to coax out of him for months.

Maybe he’s practicing how to propose with a stranger. That’s sweet, right? Like a dress rehearsal for the real thing.

The woman reaches for Kyle’s pocket, her fingers brushing against the fabric where the ring box is tucked. My stomach plummets as he pulls it out and presses it into her hand without hesitation.

She leans in, close enough to whisper something in his ear, her lips just barely brushing his skin. Kyle chuckles, his hand sliding to her waist, holding her there like it’s the most natural thing in the world.

I freeze. The truth slams into me like a wave of icy water. Everything around me fades. All I can focus on is Kyle and Not-Me, looking so cozy together.

No, no, no. This isn’t happening. It can’t be.

My body moves before my brain can catch up. I’m storming across the festival square, my boots splashing through melting puddles with vengeful purpose. The crowd parts like the Red Sea, sensing the impending drama.

“Kyle!” I screech, my voice hitting a pitch I didn’t know was possible. “Care to explain why you’re two-timing me with that wannabe runway model over there?”

The woman beside Kyle raises a perfectly sculpted eyebrow. “Actually, I’m a Pilates instructor.”

Kyle’s eyes widen as he glances between me and his . . . whatever she is. “Isla! It’s not what it looks like! I . . . I was just helping her find a bracelet!”

A bracelet. Right. Because that totally explains the way his hand was glued to her waist.

“Oh, that makes it so much better!” I snap, throwing up my hands.

Behind me, I hear Asher mumble under his breath. Oh no. He’s been recording this. The entire thing.

My humiliation is now immortalized in 4K. Future Isla can relive this disaster any time she wants.

He pulls his hand away from the Pilates instructor. “Isla, please. Let’s talk about this somewhere private.”

“Private?” I laugh again, louder this time. “You mean like how you’ve been privately seeing Little Miss Downward Dog here?”

I take a step forward, intent on . . . well, I’m not sure what. Unleashing my inner warrior princess? But because the universe has a twisted sense of humor, my foot catches on a fallen banner. Seriously, who leaves decorations lying around in the middle of a public meltdown?

I careen forward, arms flailing like I’m auditioning for a human windmill impression. My entire life flashes before my eyes, mostly scenes of me tripping over air and into embarrassing situations. At least I’m consistent.

And then, because karma clearly thinks I haven’t suffered enough, I crash right into Miss Perfect Pilates herself. We collide in a tangle of limbs and startled yelps, and I find myself nose-to-nose with Kyle’s new flame.

Not exactly the dreamy proposal moment I’d imagined.

“Oh my goodness, I’m so sorry! Wait—no, I’m NOT sorry!” I splutter, trying to extricate myself without causing further bodily harm.

Kyle rushes to help her up, swooping in like some kind of knight in shining armor. Of course, Kyle would play hero to her while leaving me sprawled on the floor.

Asher appears at my side, offering his hand to pull me back to my feet.

The Pilates instructor, looking annoyingly poised even after our collision, chooses this moment to speak up. “He never loved you.” She tilts her head and offers me a saccharine smile.

I open my mouth to argue, but before I can find the words, Kyle steps in.

“I have been trying to find a good time to tell you.” Kyle shrugs. “I tried, but we don’t really fit.”

Kyle’s words slice through me, jagged and cruel, like a blunt knife tearing through something fragile.

He pursued me while he was my matchmaking client. Dating a client is about as bad as dating your boss. He knew that. But he’s smart. Smart enough to make me believe he liked me.

And, apparently, smart enough to cheat without losing sleep over it.

I guess that’s why he was always in meetings. Way more than before. Guess some of those were with his Pilates instructor.

Funny how I kept telling myself we would work. That if I could be better, if I could just do more, maybe someday I’d be enough for someone to love. Enough for someone to stay.

But I guess I wasn’t. Still.

Not for him.

Not for the ones before him.

Not for my father .

A voice pipes up. “Mommy, is that the matchmaker you told Grandma about? Why is everyone staring at her?”

Eleanor Caldwell, a third-grade teacher at Frosthaven Elementary—who once cornered me at the grocery store to ask about my matchmaking service but never actually booked—stands at the edge of the crowd with her daughter.

Her gaze flicks to me, then to Kyle, then back to me. “Honey, let’s go.” She grips her daughter’s shoulders while steering her away.

But for every person who leaves, two more take their place. The murmurs don’t fade, they multiply, spreading like ripples on a pond.

My humiliation has an audience. A growing one.

“You’re a lying cheat!” Betty, my neighbor and my landlord, hollered at Kyle, arms crossed like she was personally ready to evict him from existence, preferably straight into a dumpster.

She’d never liked him. Not when I first introduced him, not when he started hogging my parking spot. Betty claimed she had a sixth sense for bad men.

I used to think she was just being dramatic. Turns out, she was right after all.

Kyle’s face turned red, like he suddenly realized how many people were watching. His eyes narrowed as he pressed on. “You think you’re some kind of expert on love? Look at yourself. You’re as bad at matchmaking as you are at relationships. No wonder your success rate is going down. You should fix yourself first before you try to fix others.”

My cheeks burn, tears threatening to spill over. This can’t be happening in front of the whole town.

But maybe Kyle’s right.

I am the problem . Like I always have been.

“Say one more thing, Kyle.” My heart skipped as Asher steps between us. His hand brushes against my arm, nudging me back. His broad shoulders forming a protective wall, swallowing the space until Kyle has to tilt his head just to meet Asher’s eyes.

Kyle’s mouth opens like he might speak, but nothing comes out. He shifts his weight, one foot dragging slightly behind.

Sometimes I forget how big and intimidating my best friend really is. It’s easy to miss when he’s in that worn navy hoodie, teasing me about my cooking disasters, or showing up with homemade pasta and that adorable dimpled smile. But right now, there’s nothing easy about him.

Asher steps forward once more. Kyle’s throat works, but he says nothing. His eyes dart to Asher’s clenched fist.

“You lost the best thing that ever happened to you. You were too much of an idiot to see it. And don’t even try to twist what you did. Cheating isn’t a mistake—it’s a choice. A coward’s choice.”

Asher’s hand finds the small of my back, fingers spreading gently. The scent of cedar drifts over me, mixed with that indefinable something that’s pure Asher. “You okay?”

I can’t seem to form words, so I just nod.

His mouth presses into a tight line, but his hand never leaves my back. His shoulders are rigid, tension coiled tight beneath his shirt.

I know that look. I’ve seen it before. Right before he punched Tommy Rodgers in fourth grade for calling me Little Miss No-Dad in front of everyone. Asher doesn’t go looking for fights, but when he lands in one, no one forgets.

The whole town knows better than to cross the guy who can knock out reps—or a threat—without breaking a sweat.

I swallow hard and force a shaky breath. This doesn’t need to get worse. The last thing I want is Asher going after Kyle.

“I’m fine.” My fingers nudge the side of his shirt.

His breathing is that slow, controlled way that tells me he’s counting to ten in his head. His gaze flicks to Kyle like he’s weighing his options.

And I know—if Kyle so much as breathes wrong, Asher won’t be able to keep counting.

“If I ever see you near her again, we’re not talking.”

He turns without waiting for a reply, guiding me through the crowd. “Let’s get you out of here.”

“I’m such an idiot. I should have listened to you a long time ago,” I whisper, more to myself than to Asher.

His grip on my back tightens slightly. “You’re not an idiot, Isla. Don’t put yourself down for someone who never deserved you in the first place.”

I blink rapidly, the sting in my eyes making it harder to hold back the tears. How does he always seem to know exactly what I need to hear?

“Thanks.” I look down at the pavement, not sure what to do with the weight sitting on my chest. “You don’t have to do this.”

Asher’s eyes meet mine, and his brows knit ever so slightly, a shadow crossing his face. Before I can place it, it’s gone, replaced by his usual steady gaze.

“That’s what friends are for.” He looks away.