The Dating Game- Chapter 4: The Masshole

I’m the worst, I know. It’s been too long since I’ve blessed you all with a story about my horrendous dating choices. And for that, I sincerely apologize. I’ll be better, I promise.

Let’s get right to it. This tale I have to tell is a little different from the others. Just a little. It is still poor judgement and the regret in using Tinder. I can promise you that one, it’s just a little more in depth and I got myself way too in deep with this one.

Back in Novemeber/December I was almost addicted to these horrendous apps, so this time period is when I matched with most of my suitors. Some I spoke to for a while, some were a quick conversation, some never. This may seem like useless information, but it plays into the story.

Jump to March. I am proud to say I am rarely on these apps anymore, except for when I’m bored and most likely sitting on the toilet. I went to a Demi Lovato concert and took some bomb selfies and figured “eh, let me change my pictures a bit”. I had to, I looked great. Selfie posted below. Feel free to admire my beauty. And the slight Snapchat filter that comes with it. But mostly My beauty. And makeup. Like, god damn that eyeliner.


Tinder apparently got this new feature where you could look at a feed. This feed shows you any new matches or when one of your matches added a new picture. So as you can only imagine, I received some messages after I posted it. Like, come on. I’m a dime.


**Disclaimer: If you think I am this self centered you clearly have not read my previous posts and do not understand my sarcasm. That being said, please read on.


I received one message from the boy that is the star of our story that read “Those eyes” with a bunch of the heart eye emojis. I simply responded with a smiley face and decided to call it a day. He did not. He continued the conversation asking me how I am and all that jazz. And just like that, the Masshole came into play.

As I continued to talk to this boy, I had wondered when him and I even matched. He looked familiar, but I couldn’t pin point it. He happened to be one of the dozens of boys I matched with in that dark period of mine at the end of the year. Our conversation at the time was short and sweet, and it looked like I was the one who ended it by not answering.

I noticed one other thing. It said he was 150 miles away. Where on EARTH was this dude? He told me that he lived in Massachusetts (understand his name now?), and was on Long Island for work when him and I matched. Like any normal person, I yelled at him for swiping on Tinder while he was away when he knew nothing would come of it. Normal is my specialty.

There was something different about this one. We exchanged numbers and he texted me almost every day. Not the creepy Tinder guy messages one would expect, but sweet and sincere messages. He would ask me how my day is and we would have small talk. He seemed like he cared.

We kept talking and talking. Even FaceTiming sometimes. I don’t FaceTime so this was a big deal. This seemed a lot different from the other shit show’s I had gotten myself into, and it was nice. The only problem was, he’s 150 miles away.

Whenever I brought up the distance, he would shut me up and tell me that it didn’t matter to him. Telling me that he wanted to come visit me. Telling me that he never expected to have a connection with me the way he did. And I agreed. I liked this guy, and he liked me.

This went on for about a month. One day, I hadn’t heard from him all day, and that was very odd. That night he had texted me a whole long paragraph apologizing, saying that he had a bad day at work and would normally just turn his phone off, but he cared about me and didn’t want me to think he was ignoring me. I can’t make this up.

I knew what this looked like, and I didn’t tell anyone about this really either, because again, I knew how this looked. “He lives in a different state, Taylor. This is never going to work.” I knew that, but there was something about him that felt different, and I have this weird mentality that if I talk about a potential guy in my life with anyone, then it’ll jinx it. I know, I’m weird.

That all abruptly changed, which is why and how he got the nickname he so deserves. (I am clearly playing on the “asshole” part of the name). Within a week, the texts started to dwindle. I hadn’t heard from him in a few days, and when I texted him asking if everything was okay, he told me that he had some family issues. I understood and gave him space.

I was going on a trip that week, and the last I heard from him he was texting me different sites and activities to do where I was going telling me things like “Please do this and take pictures for me” and “Maybe next time I can do it with you.” Key words, this was the last time I heard from him.

I was sitting in the airport waiting for my flight after a whole day of hearing nothing from him. I texted him telling him I was boarding and would text him when I landed. I landed, and had no texts. Not even to wish me a safe flight. Nothing.

Days went by, my whole trip went by, and nothing. I began to think something terrible had happened with his family. But he was still all over Snapchat and social media, and I can tell you this, if there was something serious going on, he made it pretty damn convincing that it was all fine and dandy.

I was hurt, and I let him know I was hurt. At this point, I didn’t care. He never answered my last text telling him how hurt I was. I never heard from him again. It was like the last month never had happened. This guy went from telling me everyday how much he cares about me, how much he wants to come and see me, and even called me “babe”. Truly perplexed people, perplexed.

This wouldn’t have worked for many, many reasons and I obviously know that, but it was nice to talk to someone that the first words out of their mouth wasn’t something disgustingly sexual or obnoxious.

I always wonder if my man-spirations read these. So I’m starting something new where I leave a little message for them if they’re lurking. So for you Masshole, I’ll say this. You did a good job of convincing me that you were different, so at least you have that. And you made it onto my blog, that’s something to be proud of. Congratulations my man.

1 thought on “The Dating Game- Chapter 4: The Masshole

  1. You will, one day soon, learn how to dance in time.


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