Let me set the scene. The story starts over winter break. I was home from college, newfound boredom and loneliness settling over me as I got back into the groove of familiarity–without distractions of schoolwork, internships, extracurriculars and the occasional frat party or two. Walking through my neighborhood, perusing all my favorite shops and boutiques, I couldn’t help but feel incredibly alone despite being surrounded by manufactured quaintness. On the one hand, I had grown a sense of detachment from the home I had left behind and felt uncertain as I maneuvered through the streets that were once so familiar to me. They had come to feel incredibly empty and lifeless, as the nucleus of my life was now housed somewhere else. On the other hand, I was being slowly suffocated by the white twinkly lights that swirled around every single tree in the immediate area, and was constantly disgusted by the handholding couples that I crossed every turn I made.

It’s no mystery that the holiday season is incredibly bleak for single people, and in my humble opinion, it’s all the handiwork of corporate America. Companies market sickeningly sweet rhetoric about loving each other, and consumers gulp it down as if it’s a 75 cent slushy  from Seven Eleven. Everyone starts snapping up significant others like they’re going out of style, and pack in as many romantic activities in as they can before the groundhog can’t see his shadow anymore.

Without work to keep me tired, school to keep me busy and social shenanigans to keep  me entertained, I remained particularly privy to all of the lovers that surrounded me, and decided to do what any other bored, lonely person between the ages of 18-30 does—I made an account on a dating app.

I was no stranger to dating apps prior to this moment, as I had made one on the night of my eighteenth birthday. I was on a spree of doing things I could do with my newfound ‘maturity’, such as getting double piercings in my ears, buying a lottery ticket and a pack of cigarettes (which I promptly threw in the trash after purchasing and taking a quick photo for memory’s sake). Joining a dating app seemed the scariest out of all these things, mostly because I associated it with waving a metaphorical white flag.

Making a dating app meant that I had failed at finding a boyfriend in real life, and had to turn to selling myself through a screen to snap the trap, which at a mere eighteen-years-old felt, for lack of better word, embarrassing as hell. To me, online dating was inauthentic, gross and at the base level, an exhausting game of weeding out gremlins in snapbacks looking for boob pics as jack-off material. However, I would find a nugget of optimism when I stumbled upon intellectually stimulating guys who were a) age appropriate b) used proper spelling and c) weren’t wearing Sperry’s in their pictures (I really don’t think this criteria is too absurd! But believe it or not, they’re few and far between.)

I even met a few of them in person, and it went well, but none came to fruition, as school schedules, geography and desired outcomes put a wedge in my hopefulness. Although none of them went anywhere, I still don’t consider them failures, as they allowed me to maintain optimistic that if there were at least a few guys I could be remotely into within the thirty-mile radius of my area, then there had to be even more beyond that I simply hadn’t swiped right on yet.

Anyway, the point is that I had went through this process on and off for the preceding two years, and after the wintertime loneliness mentioned above hit, I decided to stuff my preconceived notions of online dating into the subconscious once more, and give it another try.  Most of my swiping was uneventful, save for the few times I stumbled upon snapback gremlins I went to high school with, who I quickly swiped left on in hopes of removing myself from their stack before it was too late.

But then, all of a sudden, I stumbled upon the photo of someone I did recognize, and the sight didn’t make me recoil. He wasn’t a snapback gremlin, but instead someone from my past that I never thought I would see again, although I subconsciously had always hoped I would. Jack (whose name has been changed for confidentiality purposes) was my elementary school crush. We were in class together all throughout our childhood, and almost all his photos in my yearbooks are surrounded with a magic marker heart.

I genuinely felt like mine and Jack’s childhood connection would go beyond the confines of our elementary school one day.


I wouldn’t define myself as a “boy crazy” child, especially because the title comes with the assumption that you are crazy for many boys at once. Although I had cheesy snapshots of Justin Timberlake, Corbin Bleu and Jesse McCartney adorning my walls, the only boy on my plane of reality that I was truly crazy for was Jack. Unlike all the other boys in school who loved to pick on me for my whacky outfits, overactive imagination and habit of hiding behind the jungle gym at recess to write stories on scraps of construction paper contraband, Jack was sweet and empathetic. He never made fun of me or my interests or made me feel like the biggest freak on planet earth, and for that, I was always grateful.

“There’s something about him that’s…different, than the other kids,” My mom insisted to me on the ride home after bringing cupcakes to my first grade class during lunch period, where she finally got to meet him and see his brilliance and magic I had told her about every evening after school.

Throughout the years, our friendship kind of fizzled, especially as we looked forward to middle school, which entailed us going to different places. I refused to acknowledge that it merely could have been my crush talking, but I genuinely felt like mine and Jack’s childhood connection would go beyond the confines of our elementary school one day.

“Life is funny sometimes, you could run into each other again.” My mom told me as I had a dramatic, pre-puberty-induced breakdown on the last day of fourth grade, which was to me the last day I’d ever see jack again. “You never know.”

Upon matching on the app, what followed was a weeks-long back and forth of catching up, reminiscing and a little bit of flirting sprinkled in. I was excited and perturbed, I knew life was “funny”, but didn’t quite believe my mom when she told me so in the midst of my fourth-grade meltdown. I loved the idea of meeting again one day, when we had grown up and become who we were supposed to be, but I decided that was entirely too cliché and reserved solely for the plot of some Hallmark RomCom that had yet to be released.

However, this was indeed happening to me, in real life, and there was nothing imaginary about it. And the best part was, Jack was still the same sweet, funny, cute boy I had known all those years ago. He had grown up, developed interests, aspirations and perhaps a more extensive vocabulary, but other than that, he hadn’t grown into someone I didn’t know or didn’t like. We talked about everything under the sun, and realized just how much we had in common. The most magical part of it all, was the fact that I didn’t feel like I had to alter who I was to make myself more desirable to him. I was never worried the things that I said would be taken wrong, or that he’d think I was strange and go running for the hills. In my past experiences, it felt like I always needed to become a lighter, happier, less intense version of myself to be well liked. But with Jack it was easy. Almost too easy to be real, especially to my cynical heart, which had been stomped on one too many times by total losers.

By remaining on my screen, it stayed close to my heart, where it was still pure and perfect and simple.

But it was real. So real that, within a few days of talking, we had our first date planned. I was on Cloud Nine, so excited that I was hesitant to tell any of my friends, mostly because I was cautious to keep the happiness and excitement preserved. I didn’t want to speak too soon, have things go wrong, and then explain to them later why it didn’t happen.

Days passed, and although we were talking almost every day, we never fully nailed down a day in the calendar for the date he had said he was so adamant about taking me on. I tried to not think much of it, insisting that it would happen when it happened, that I had time before I had to go back to school, which was on the opposite side of the state from his. Besides that, I was content with the back and forth late-night conversations, feeling like I always had someone to talk to, about anything at all, without being judged or misunderstood. By remaining on my screen, it stayed close to my heart, where it was still pure and perfect and simple. It felt safe that way, and while I wanted nothing more than to see him in person (and potentially kiss his face or something), I was perfectly okay with settling for digital communication. Although I knew in the deepest parts of my heart that this probably wasn’t good, and that red flags were popping up left and right due to his lack of acting on his promises, I refused to see them by simply looking the other way.

In my everyday life, I’ve always prided myself on being a pragmatic person. I’m usually the voice of reason for my friends, and can almost always snap myself out of whatever crisis I’m in to think about it from a logical point of view. But something about Jack made me divert from this habit; as my default defensive response came out, she would quickly be shushed. I wanted to believe that it was fine, that everything was normal, and that I didn’t need to turn into the aggressive, problem-seeking, rigid Olivia that arises in compromising situations. After all, she was the one who had never had a “for real” boyfriend, which had to say something, right?

So, I let things run their course. I continued to correspond with him until January, when it came time for me to load up my things and head West, while he headed East. The night before I was to leave town, he explained how upset he was that our schedules hadn’t allowed us to meet, and asked if we could continue to stay in touch throughout the semester until summer when we’d both be in town. I (I being the new, not-problem-seeking Olivia) said ‘of course’.

We continued to do just that, until busy schedules caused our contact to dwindle, and from March to May we didn’t speak at all. I got caught up in school and work, and made plans to devote my summer to writing and traveling. Although Jack was always on the back of my mind and would creep up to the forefront on nights that were particularly lonely (of which wine was almost always involved), I started to feel okay with the idea of not being in constant correspondence.

The uneasiness of radio silence was better than the fear of shouting out into the void, and not hearing anything back at all.

Part of me wanted to reach out, to ask how he was doing, what classes he was taking, why he had disappeared. But something kept me from doing it, as I was paralyzed by the fact that I didn’t think I had the right. The intangibility of the whole thing made me uncertain about the “rules”, which I was so afraid of breaking. There was no label, we hadn’t even met in person yet. How crazy and pathetic could I be to think he owed me any sort of explanation, or that I had the right to reach out at all? No matter how much I’d like to deny it, I am, at the deepest truest parts of my being, a rule follower.

I thrive on boundaries, labels, clarity. I like to know what’s up, and when I don’t, I feel uneasy from head to toe. You can imagine my distress when it came to mine and Jack’s status, and how to proceed. Although I knew that, when it came down to it, we weren’t anything at all, I still couldn’t help the feeling in the pit of my stomach that was keeping me from forgetting it. Even if we hadn’t met in person, we were bound by the cellphone signals that allowed us to be in constant communication, and the history we shared. It was for this reason that I refused to let go, and decided to keep it preserved by not saying anything at all. The uneasiness of radio silence was better than the fear of shouting out into the void, and not hearing anything back at all.

So, as winter finished off and spring rolled in, I left it alone, keeping it tucked away safe in its own separate part of my heart. The flowers bloomed, final exams approached and slowly but surely it became easier to stop worrying about Jack, even on the Saturday nights when I’d had a few whiskey cokes in my system and was sobbing to 70s country ballads on my bedroom floor, or jumping up and down on the mildewy couch of some frat house with my friends.

And then, on my first night back at home for the summer, my phone let out a little ding. I paused the pirated rerun of Dr. Phil I had found online and picked up my phone to see Jack’s name on my screen. That little dormant place in my heart I had reserved just for him had been awoken, and I nervously bit my thumbnail as I waited until it was an appropriate length of time to reply. We exchanged the trivial how have you beens and lamented over our shitty semesters, but Jack didn’t waste much time before asking me about the date we had planned to plan months before.

I was a little taken aback at his response. Although I was overjoyed that he wasn’t totally “over me”, and was finally doing what I had hoped he would do for the past two months, something about his pushiness felt inauthentic, out of line even, especially considering we hadn’t spoken in a while and he had said he was going to take me out and then never did. Again, the Old Olivia would’ve confronted him, been tiffed by the fact that he thought he could waltz back in whenever he wanted and act as though everything was fine. But, I saw this as a small window of opportunity, that if I wasn’t at the ready to see him whenever his schedule allowed that it would never work. Again, Old Olivia didn’t have much success with her methods in boy’s past. So, I told him the days I was available, and eagerly waited for a response.

A few days passed, and the same silence I had gotten so comfortable with over the past few months happened again, and settled in me like a feeling of worry that had made itself comfy at the pit of my stomach. It lingered as I caught up with old friends, snuggled my dog, painted my nails. Before I knew it, I was packing my things and preparing to ship out for a month-long expedition along the East Coast, which would yet again put a barrier between Jack and me meeting being in the realm of possibility. The radio silence continued.

She was the type of friend that would have you doing the thing your Mom always said not to do, but once you did it, you felt like a total badass.

As I sat in a bus headed towards upstate New York, I pondered over what had transpired, or I guess I should say what hadn’t. More than anything, I was confused. The back and forth disappearing act he had put on was impossible for me to comprehend. I wanted an explanation, to know why he was doing it, why he would leave and come back and be all about it, just to leave again. Questions were racing through my brain, had he changed his mind, or even worse, found someone better?

At a truck stop in Pennsylvania, I stepped out of the bus to check my phone and sit in the sun while we got gas. While eating some trail mix and replying to emails, I received a text from my old friend, Sarah (whose name is also changed for confidentiality). Sarah and I were inseparable for the first twelve-ish years of our lives. Although we went to different schools for all of it, we always made a point to come together on the weekends for slumber parties and fun adventures. Sarah was always the outgoing one, the brave one. She was the type of friend that would have you doing the thing your Mom always said not to do, but once you did it, you felt like a total badass. I always admired her, for her blondness and fearlessness and ability to say and do whatever she wanted. Although we were complete opposites, we worked well together, and spent most of our adolescence scheming around each other’s neighborhoods, making silly videos and baking cookies in the middle of the night, stifling our laughter so that we wouldn’t wake up our parents.

I was a little surprised to hear from her, especially because we had lost contact in recent years. I was especially surprised at the message she sent.

You won’t believe who I went on a date with last night.

A lead ball rolled to the pit of my stomach. It couldn’t be. I prolonged my response time, just so that I could remain in the mindset that it wasn’t who I thought it was for a little bit longer.

They went to high school together, had tons of mutual friends, started texting back and forth, you know the story. He asked to take her to dinner, and she said ‘of course’. She gushed about how excited she was, that he was so sweet, that they already had their next date planned. The hopefulness in her tone was familiar, and sent me back in time, to the twinkly lights and the handholding couples and the jolt that flew to my fingertips whenever my phone would let out a ding to notify me of his response.

In my eyes, I was supposed to be the one overflowing with excitement, recounting how sweet he was and how the stars were aligning, and the birds were chirping and everything was perfect. But I wasn’t. Instead, I was listening to Sarah, my former best friend, in all her blonde, fearless glory, planting herself in the story that was supposed to be mine, and running off with it.

Sometimes I get so wrapped up in the person that I want them to be that I become oblivious to the person they really are


I couldn’t bring myself to tell her the truth of the situation. I decided it wasn’t worth it, she had no way of knowing, it was just a shitty coincidence that it happened to be her. It would have been easy for me to blame her, to say it was her fault for taking Jack from me, but that would be silly, especially because the Jack that I thought she was taking didn’t really exist at all.

Something that I’ve struggled with for a long time, and still do to this day, is comprehending how someone could do something that I wouldn’t do. Why would someone act so interested, only to disappear and go out with someone else? Besides that, he knew Sarah and I were friends. How could someone knowingly do something like that? I guess it’s incredibly self- centered of me to assume that someone would live by the same carefully curated principles I live my life by, but I can’t imagine how someone would have this in their division of totally okay behavior.

In the past, I have been guilty of imposing unrealistic expectations on people I meet and become close with. Sometimes I get so wrapped up in the person that I want them to be that I become oblivious to the person they really are, and when that person presents themselves so aggressively that I can’t ignore it, I’m angry and taken aback, shocked even, that they aren’t the person who I had essentially made up in my mind.

Although I was talking to the real Jack, the further in I got, the more I started to craft a Jack in my head who, dare I say it, didn’t exist. This fake Jack would never keep me on the line, play me for a fool, or knowingly go out with my former best friend during the process. But, the truth of the matter was that the real Jack was someone I didn’t know at all, that I had only communicated with through a screen, where he could say or do anything he wanted whether it was genuine or not. I simply made the mistake of believing him, buying into the idea that a romcom plot could unfold in real life, and filtering reality with the Jack that I wanted him to be, that I had created out of the desire for something real and good. 

I don’t think that Jack is a bad person, and although I was initially blanketed with overwhelming disappointment, I’ve reached a place where I don’t blame him. I don’t feel vengeful or hurt, especially because when it comes down to it, he never owed me anything. Although we had built some sort of “internet bond”, we were never in a relationship. There were no boundaries formed, or rules, or any discussion on how to proceed. If I’m being incredibly honest with myself, I skeeted around that conversation just as much as he did. I didn’t want to bring it up because deep down I knew the answer I would get, that it would force me to see that the idealized version of Jack I had created wasn’t real, and that feeling was, in my mind, worse than remaining vague and digital.

We owe the truth to ourselves, even if it’s not exactly what you had hoped it would be.

One of the biggest mistakes I made throughout this whole process was suppressing who I really was, my principles, my gut instinct. I thought that passivity was the way to get him to become what I wanted, that because “problem-seeking Olivia” hadn’t managed to get a boyfriend yet, becoming someone completely opposite was the only solution. How could I be mad at Jack for not being genuine, for scheming around behind my back, when I wasn’t being the most authentic version of myself either?

Maybe if I hadn’t done that, I wouldn’t have had to go through as much pain, if I had realized all of this sooner, that I wouldn’t have become so attached to fake Jack. But, I’m almost glad it happened, because it made me trust “problem-seeking Olivia”, and realize that she isn’t problem-seeking at all.

If I took anything away from this whole ordeal, it’s that I should never ignore my gut feeling, or try and mask who I am, or mask someone else with an idealized version of who I want them to be. And if you take anything away from reading this, I hope it’s that you should always trust what your heart is telling you, and strive for authenticity, because we owe the truth to ourselves, even if it’s not exactly what you had hoped it would be.