Seeing Someone Out Of Your League

Six hours into our second date, I was exactly where I wanted to be with the cute junior pre-med student I’d been fantasizing about for months. We’d just finished our post-comedy show dinner at a 24 hour diner and had walked back to the parking lot to find his car (Featured image is my date night outfit). The meal had gone perfectly in every way I would have liked: we played off of each other jokes well, switched naturally from conversation topic to conversation topic, and felt hours go by like minutes as we sat across from each other. Although we’d been chatting nonstop over breakfast foods, when we strapped ourselves into our respective seats, we were silent.

I fully intended on leaving this date with a kiss, and I had to leave the right cues.

He handed me his phone to route Google Maps back to my hotel. I clicked the power button to open it.


I toyed with the fabric of his case, then dragged my fingers across the screen to slide the phone open. Passcode. Leaning over to the driver’s seat, I held out the phone for him to type it in.

He didn’t bother taking the phone from my hands. Instead, he wrapped his around mine and used his thumbs to enter the four digit code. It unlocked, but our hands still lingered. I adjusted myself further to his side of the car so that my arm could press against his.


“So…” I said. “It’s time, I guess.” I looked up at him and traced the outline of his face with my eyes. “To take me back to the hotel.”

He took in a breath before speaking. “Yeah.”

I pointed to the directions that appeared on his phone. “That’s the way.”

He batted his curly lashes. “I guess it is.”

“We have to,” I outline the route with my finger, “go this way.”

“That,” he adds, “seems like the right way to go.”


Our nonsensical banter continued for another minute or two. I could tell that neither of us had been thinking before we spoke, or truly listening when either of us had. We had been waiting for the other to find an excuse to slow time down further, and our drawn out observations of the obvious were just filler.


We’d reached a point where talking no longer seemed necessary. Instead, he fixed his eyes on mine and I fixed mine on his. Silence.


F*ck it.

I leaned over the armrest console and kissed him. He responded quickly and pulled me in by the back of my neck. Gentle and a little slobbery. Every boy kissed differently and I tried my best to analyze and match his energy. When we got into rhythm I kicked my shoes off and sat on his lap, straddling him. Sometimes, in between breaths and kisses, I opened my eyes ever so slightly to catch a glimpse of the curly haired blonde boy whose arms wrapped tightly around my body.

To add to the urgency and further build tension, I would pull away to make a light joke.

“You finally got me to shut up,” I teased.

“I know.” He paused. “So refreshing.”

He leaned in to continue kissing me, and although my body followed, my mind trailed off.

Was that the catch?

His hands on my thighs made me shiver. Goose bumps, wet lips, tongues, saliva.

He endured months of chatting and two six-hour-long dates to finally get me to shut up.

Fingers crawled up my back and played with the straps of my overalls. Toying with the buttons of his flannel, I popped one through its hole then led my index and thumb down the fabric to the button underneath it. Pop. Pop. Pop. 

He stuck around this whole time just to sleep with me. 

With my hands on his chest, he inhaled deeply and pushed his hips up against me. Short moan. Exhale.

He doesn’t like me and I can’t even blame him for it.

All of a sudden, all I wanted to do was escape my own body. I felt embarrassed and naive. How did I not see this coming? Why would someone like him ever consider me as more than a vessel for his sexual pleasure? Isn’t that how every boy I’ve genuinely liked treated me, after all? I started doubting everything about myself.

You’re not white enough. Pretty, light-skinned, half-Mexican: enough to brag about, but too exotic to be seen as anything more than a conquest.

You’re not smart enough. Chews your words when you speak. Has to Google the word ‘Anachronistic’ under the table when your date uses it at dinner. 

You’re just not good enough for someone like him. This isn’t a movie. Sheltered, Upper East Side born, New York native in her privileged bubble getting the guy just wouldn’t be fair. 

You’re a rebound. A fetish. A dumb 18 year-old city kid. He called you chaotic once, and now you hear it in a different light. Crazy. Irresponsible. Not bring-home-to-parents material. A man like him needs someone more mature. Someone with more life experiences. More bullet points underneath “special skills” on their resume. More quotes from 18th century philosophers ready to be pulled out in everyday conversation. More impressive. Less you.

I pulled away.

That was about two weeks ago, and although I’d left that second date excited to see him again, I still couldn’t shake those insecurities out of my head. He clarified that he was just teasing me. That he liked talking to me because I was fun and interesting. That he was excited to see me again for a third date when school was to start back up again and so it was a shame that he wasn’t going to see me sooner. But still those two words lingered: so refreshing.

“Can I be honest?” I’d at one point said softly, cradling the back of his neck with my palm.


“So, we established that we both found each other super cute during first semester psych, so you want to know something funny?” He nodded while I began to sit up straight as I continued. “Well, I was thinking to myself, ‘If he’s that cute, there’s no way he can be interesting!'”

“You can’t do both,” he joked, smiling.

“So, Charlie. What’s the catch?”

He laughed and kissed me on the nose.

In the moment, my comment came off as an endearing compliment from the cute girl who’d sat two tables away from him in class, but the sentiment was genuine. He was perfect and I wasn’t good enough for him to want me. And after I heard him tease me about my silence being the highlight of his evening, I felt a little worthless.

When the night ended he gave me a kiss goodbye and dropped me off at the hotel I was staying at for Fourth of July weekend. It was three in the morning when I’d finally thrown myself onto the big white bed of my hotel room, careful to not wake up my friend Nadine who was fast asleep in the bed next to me. All I could think about was how that boy had kissed me and so I was giddy and smiley at the prospect of a new relationship, replaying our first kiss over and over like a movie scene.

That being said, I’ll just shove my skepticism to the back of my head for now. There’s about a month and a half in between now and our planned third date, so those thoughts have been creeping up on me at the most inconvenient times. However, I refuse to let my cynicism discourage me so early into this new infatuation. I’m clinging to the idea that a boy who treats me with respect and dignity exists, but I’d be lying if I said I wasn’t waiting for him to prove me wrong.

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