Just a little aside about today’s entry. This contestant actually sent us two dating horror stories from her own hilarious blog. In the interest of fairness, we picked one for our contest, but let me tell you, they are both amazingly awful and therefore definitely worth reading. You can see the original posts, complete with delightful gifs, here (for the story below) and here (for the story we didn’t post). Happy reading!

Entry #4: Six Hour Date

Submitted for the approval of the Midnight Society, I call this story: The Tale of the Worst Date of My Existence.

Haha, sorry I had to go all 90′s Nickelodeon on you. Since my online dating life is over, I figured I’d share some of my dating nightmares with you. This one is going to be lengthy, but this date lasted 6 hours, so there’s a lot to report.

I started talking to Q* back in early May. I honestly thought he was the total package: Good looking, funny, wanted to be a Hollywood writer (THAT should have been a red flag), and our conversations seemed to flow so nicely. Out of all the guys I spoke to, he was the only one I had a good feeling about. Ugh, I was so wrong.

So finally after a few weeks of getting to know each other, Q and I had made plans to meet up the next Saturday in Boston and spend the day together. I was a little nervous about meeting him because it had only been the third guy I was going on a date with, so a few days before the date we FaceTimed. Once again, conversation went smooth. He was a little shy and quiet, but I took that as him being nervous and just brushed it off.

Fast forward to Saturday. I decided to take the train into Boston because I didn’t feel like paying for parking. FIRST MISTAKE. Side note: The train runs every THREE hours, so if you’re in a rush to get out of the city, don’t even think you’re getting out when you want to. As soon as I met Q at the train station, I had a really odd feeling in my stomach like something wasn’t right. THAT, my friends, I was right about. He was NOTHING like I thought he would be. Sure, he was still good looking, but OBNOXIOUS. So. Effing. Obnoxious. As soon as he saw me, his true personality came out.
He wanted to take me on a Duck Tour, which for those of you who don’t know what that is, it’s a trolley-type tour around Boston where they end it off with the trolley going into the water (relax, it turns into a boat) and you get to see all of the major sites in Boston. Cute idea, BAD person to try to do this with. Instead of asking where the pick-up was for the trolley, Q decided it would be the smartest idea EVER to just walk around the city for hours looking for it, which lea to eventually missing the entire tour. The entire time we were walking around the city, Q was shouting random movie quotes into the streets while holding onto me like the wind would blow me away if he let go.

“DON’T FORGET TO BRING A TOWEL,” he screams to a bunch of little children and their parents.

This went on for the entire hour. SCREAMING into the streets, sometimes at people and other times-at nobody. I was mortified. Then, as we took trolleys to all of the places he THOUGHT we were going to, he just felt the need to make me even more uncomfortable. He proceeded to keep his arm around me the ENTIRE TIME we were next to each other. He’d caress my arm and then POKE me and giggle. Like a flipping child. I’d remove his arm from me and he would PROCEEEEEEED TO CONTINUE to wrap himself around me. I was literally reciting “Our Fathers” in my head and then telling God this was NOT funny.

Finally after traveling for hours to nowhere, I thought of an exit strategy. I had to get out of this date. I told him I had to babysit my niece and had to be home by a certain time. He said it was totally fine and I thought I was home free until I checked the next train time. I had apparently JUST missed the train and the next one wasn’t for three hours. THREE HOURS. YES PEOPLE. That means I spent 6 hours on this date from the depths of Hell. So what did I request we do until my train arrived?

Get drunk.

Very, very, very VERY drunk.

So we proceeded to bar hop for a few hours. He honestly got easier to talk to as the drinks went down. The date just completely went down the shitter from the first bar we went to. He proceeded to tell me that he was bipolar and used to be suicidal and his mom left him when he was a child and stujhisdghkldfhgdioghifghofdghsioghsifdoghioshioghdsioghif.

Now, I’m not one to judge. I consider myself an equal opportunity employer. But on the FIRST DATE? Really, Q? I had such high hopes for you and they just burned to the ground. Then, he started asking everyone in the bar to take pictures of us. He said we had a great connection-something was there. I wasn’t like the others. I would interrupt him and say what great FRIENDS we made and then he would poke me, smile, and throw his damn arm back around me. Lord, have I sinned that much in my life to deserve this?

So finally, the time came when my train was about to come. We started walking to the station. Q was hiccupping because he tried to keep up with me and got wasted instead. As we walk to the train station, all of a sudden I hear something fall on the ground and make a couple of clanking noises. I thought to myself, “What was that?” So then, Q gets down on all fours and picks something up from the ground. As he stands up he smiles at me and holds his hand up. “Well, I guess it’s time to be honest,” he says as he smiles at me with his FRONT TOOTH COMPLETELY MISSING.

Yes, people. You heard it here first. He held in his hand his fake front tooth, which after a few minutes of him talking he then proceeds to put said dirty tooth back into his mouth. My heart just sank. Honestly, after the entire day I had, that was just the icing on the cake. I didn’t even flinch. That’s exactly how it was supposed to happen. After the whole day of touching, poking, and yelling, of COURSE he was going to miss a tooth. My luck.

So to wrap it up, my train came. Missing tooth boy grabbed me and tried to kiss me, but I put my hand up. YUP. Right all up in his face. After how I acted distant ALL day, how can you think it’s okay to GRAB ME AND DRAG ME IN FOR A KISS? Nah, nah boy. I don’t play like that. Sorry.

I get home and receive a text from him that read “So glad I met you today. We have such a connection. All that was missing was a romantic dance between us. Next time, Gadget. Next time.”

And that’s when I let him down gently. I told him he was sweet, but I didn’t feel a connection. He just replied, “Ok.”

DUH, DUDE. DUH.