Chapter One
- Oaklyn -
Swiping right is simple, but getting a decent man takes strategy.
Online dating, in general, is a wild card. I'd imagine it like being caught in the minefield of Minesweeper. You never know when you're going to stumble upon an explosive match. It's going to take more than a stroke of luck and street smarts; it requires a backbone. This is why when my best friend deliberately asked me to be her wingwoman in the hunt to find her future hubby, I knew it was time to level up to the plate.
I've swiped left on so many guys that I am giving myself the title of a proficient heartbreaker. At least, Sailor, has me to help her dodge those online dating landmines. Who's to say? Maybe today is the day we'll strike gold and find a real gem. Or, hopefully, a gym rat who doesn't think mirror selfies are the zenith of dating profiles.
"Go back to the last one," Sailor, my best friend instructed. "No, I meant the one before that."
I paused, glancing up briefly before hitting the rewind button. Two profiles back, and there he was the so-called thirty-nine-year-old who clearly had decades on that number. I was aware that generational aging is a thing, but this is absurd. My bluff radar was off the charts; this was easily a classic case of catfish.
I cringed deeply. Sailor's taste in men was eclectic. More diverse. Though, that's the kind of thing that solidifies a long-term friendship, isn't it? When one finds a potential match a catch and the other is biting their tongue to find even a sliver of something nice to say.
"Sailor," I said.
Her orbs widened as she chewed on a swaddle of lo mein noodles. "What?" she murmured.
The incessant slurping is driving me up the wall. My patience is thinner than a pancake, all because of my DIY diagnosis of misophonia. I haven't gotten an official diagnosis, but I swear there's something to it. Either that or Sailor is just a notoriously messy eater.
"This man is nearly pushing at least twenty years older than you."
"And?"
"And . . ." I shifted my desk chair to turn my attention fully towards her. The phone in my hand becomes aligned with her vision and we're both skimming the screen in union. "This is not a husband, Sailor. This is what we call a sugar daddy."
The evidence was all there. The silvery hair, the receding hairline, the neck that told a thousand tales of years gone by. I was highly convinced that this grandad might of invented online dating as one of its founding fathers.
Sailor smirked as a curveball. I wish I could rip out my eyeballs, drench them in bleach, and pop them back in.
"Maybe that's what I want."
Reaching my patience, I tossed the phone on my keyboard mat and groaned loudly. This was getting nowhere. It was equivalent to trying to sail a ship with a broken rudder. And this is one of the reasons why 'Captain' Sailor's dating history hasn't been necessarily smooth sailing. Every time I thought we were making headway, we'd get thrown off course by another gust of wind. She kept getting caught in riptides of bad choices, tossed around by the waves of disappointment. It was as if she was destined to be shipwrecked on the shores of heartbreak, over and over again.
A best friend can only take so much before all intrusive thoughts claw to the light.
"Well, if you start getting senior citizens discounts, the least you could do is take me out for brunch," I shot back, only receiving a shaky chuckle.
I have been supportive of all her wild decisions. I deserved some sort of medal for my loyalty in return.
I took a deep breath and handed the phone back to her. "Okay, let's switch it up." I proposed a new strategy forming in my mind. "How about a game of smash or pass? We only swipe right when we both give a thumbs-up. Deal?"
"Sure, whatever," she replied, tucking her ebony coils behind her ear and scooted closer to agreement.
I nudged my soy sauce-laden rice to the side, careful not to stain my work attire. I have an upcoming meeting with a soon-to-be-wed couple, later and wearing white while scarfing down takeout was probably not my brightest idea.
I watched as she set the original features back onto the app, starting over our search from the start. The first guy that pops up on the screen appears to be quite the catch.
"Smash," I declared with a sly grin, my finger pointing towards the man in the velvet navy blue suit. The man exuded sophistication.
Sailor wrinkled her nose, dismissing him with a shake of her head.
"Pass. He screams narcissist."
"In what way?"
"High net worth, even higher ego."
I was momentarily speechless and allowed the quote to soak in. She was right; the tailored Valentino suit hinted at more than just style.
"Ah, now I see it."
Sailor hummed knowingly and folded her arms. "It's not all about the pretty faces, you know. Sometimes, you just need to take a look at yourself in the mirror."
"Do you think I'm a red flag?" I challenged. The playful banter had turned the spotlight on me.
"Gushing red."
It couldn't have been more obvious. I like to think of myself vibrant shade of red.
Keeps things interesting, right?
We flicked to the next page. Our attention landed on a man with curly hair and a woodsy vibe—he looked nearly a spitting image of one of Sailor's toxic exes. Instantly, memories of Sailor's ex from junior year of college flooded my mind, a guy who had nearly left her with an unwanted souvenir.
All I vaguely can remember from the memories are late-night visits to the corner stores and nail-biting visits to the on-campus health clinic. Not once. But Twice.
To sum it up, Sailor narrowly avoided a close call. Or did she? One of those two times was very unclear to me.
Anyway.
Dominic had the rugged appearance of a brawny lumberjack, with a million-dollar smile that seemed tantalizingly close to our office. Yet, despite his charm, Sailor's heart seemed a million miles away from him. Her face fell into a frown as she scrutinized his presence, and I could already sense her inevitable response.
"Oh, that's for sure a hard pass," Sailor announced, gagging. "He looks like Tyler, does he not?!"
"Trust me. He does . . ." I trailed off. "Wait, that is Tyler!"
Sailor snatched the phone and gasped. With the device now inches from her nose, she eyed the photo as if she had a few last words to say. Tyler was posing under the name Dominic. It was hard to forget a face like that. On a scale from one to ten, Tyler was a ten in looks. Rating his commitment in relationships, though, this guy shouldn't be allowed to take a weigh-in. He was the lowest of lows.
After experiencing the madness behind my best friend's relationship, that was one of the reasons why, I, myself don't enjoy commitment. Tyler was the prime example.
"The mole underneath his eye is a dead giveaway," she and pushed away the phone. "Get that away from me."
I had no complaints about that one.
Onward to the next!
"Alright, let's do one more." I am determined to lift Sailor's spirits as we continue our search.
And that's when I saw him. The man with the black, tousled hair and the washboard abs that could rival those gracing the pages of a glossy Vogue magazine. My mouth practically watered as I stared at his picture.
"A hundred percent smash for sure!" I exclaimed as I drooled over his image.
I persuade the dating app.
The attractive gentleman owned a fit physique that hinted at his dedication to a healthy lifestyle. His seductive umber-colored eyes and midnight hair beacons a smile that was both warm and inviting. Notefully adding to his irresistible smile, the ivory fences of his teeth and pacific ocean-deep dimples were a combo that no one could ignore. His profile railed me, activating my novelty about the person behind the photos. I wondered what it would be like to connect with him physically beyond the confines of the app.
"Boston," Sailor leaned in closer, peering at the screen as she zoomed in on his profile.
"Journalist from Orlando, Florida," she read aloud.
I then joined in, reading his bio.
"He's twenty-three, enjoys long walks, and graduated with a journalism degree from the University of Miami over a year ago."
Sailor nodded, impressed by his credentials. "He sounds like quite a catch."
I wrinkled my nose. "Except for the part where he talks about his undying love for sea turtles. That part gives me a bit of the ick," I added. I'm not exactly an animal person. At all.
I went on, probing, "So, are you going to swipe right?"
Her expression clouded with uncertainty.
"Yes, I would love to," she began hesitantly, "but probably not. I have a weird feeling about this one."
"Sailor," I warned. "You made a deal. Whoever we both agreed on, you would swipe. What the hell is wrong with this guy to give you doubts?"
Sailor, being the free spirit that she is, latches on to the crescent-shaped moon phase necklace and the tiny crystal attached. She closes her eyes to concentrate. The universe is evidently presenting guidance.
"I'm sensing some bad juju," she replied.
"Bullshit." An eye roll is well-deserved for her outlandish assumptions. "A genie could grant you a wish for the man of your dreams and you'd still call it a hunch," I exclaim.
She narrowed her brows.
"The crystals never lie," she declared,
I'm partly, or mainly, to blame for this sudden spiritual change. Around her birthday several months ago, I had gifted her an extremely last-minute present. What she still doesn't know is that I'd grabbed it at the tourist gift shop near my office and bought it for less than ten dollars. Well, three. The owner gave me a deal, where I traded the remaining balance for a Snickers bar and a bottle of water.
In short, Sailor believes is from some high-end crystal shop when in reality the necklace is dirt cheap and holds no real spiritual or dollar value.
But I made it up to her for Christmas, that's for sure.
I continued scrolling through the feed, my eyes landed on him—the Miami hottie with the killer career, washboard abs, and the ideal proximity to our office. It was an opportunity that seemed too good to pass up. Sailor, on the other hand, was being a total killjoy. If she wasn't going to take this chance, I entertained the idea of swooping in and claiming him for myself. The anticipation was almost tangible; I could almost taste the sweetness of his lips.
I needed to get ahold of myself. Fast.
"I think he's a great match for you, Sailor."
Sailor stood to her feet and paced the room. When she does this, it's usually an outcome as no as a final answer. Her shoes were scuffed on the floor as she halted. "Okay, then. If he's such a great match, why don't you hop on the dating app and swipe on his profile? He's more of your type anyway."
Dark hair, successful career, dimples? Yes, he's very much a perfect description for my type.
But this isn't about me.
"Ohh . . ." I flinched at her words.
"What?" Sailor questioned, confused.
A chill ran down my spine. "Don't ever put me and the word 'dating' in a sentence ever again. Next time give me a warning."
In the past, I, too, had been a self-identified serial dater, until I realized that it was better to be single and fabulous than stuck with someone who failed to appreciate my worth. In a nutshell, I was more of a 'drop them like flies' type of girl.
I'm all about swiping right just to land in his arms. I think of it like borrowing Wi-Fi at a coffee shop: strong, reliable, and absolutely no long-term contracts. Perfect.
However, I found myself growing increasingly agitated as Sailor hemmed and hawed, her face contorting with indecision. This dilly-dallying was driving me to the brink of madness. My fingers itched with impatience. I understood her reservations when it came to relationships, but this was crazy. We're never gonna find a match at this rate.
Should I make the first move? I pondered, questioning the danger of such an act. It was worth the try.
Ah, to hell with it, I thought, throwing caution to the wind.
With a quick swipe to the right, I acted upon my decision. After all, what harm could it do? Sailor would thank me later.
To my surprise, when Sailor caught sight of what I had done, her eyes nearly bulged out of her head. Her reaction was priceless. "What the hell did you do, Oaklyn?" she practically shouted. I hushed her, hoping to keep low-key in this professional setting.
We didn't need the whole office to know our shenanigans.
"I just made your life easier."
But Sailor was far from thankful. She paced back and forth through the office even more, before snatching the phone. Her fingers made an upward movement through the online feed with an almost frantic intensity. The deed was done.
"So, what now?" she asked, defeated, knowing there was nothing else she could do.
"Now," I replied calmly, kicking up my feet. "we wait."
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