Updated: Apr 19
Want a look into my past dating disasters? Read about the three longest dates of my life in what I like to call The Relationshit Show.
At twenty-seven years old, I haven’t been on too many dates. I had a long-term boyfriend in high school, dating him from freshman year until senior year. We took a tiny break while I tried to date my best friend . . . that story alone could fill an entire book . . . and then we got back together for another year and a half.
After him, I was in a relationshit (that’s not a typo, people) with another guy for three years. He cheated on me for two out of those three years and after we broke up, I’ve been single like a pringle for close to six years. Unless you count the two months I thought I was somebody’s girlfriend, but then after he decided to become a zombie after he ghosted, he said something along the lines of ‘you know when we were trying to be exclusive?’ If I could enter a straight face emoji into this text, I would. And if it is possible, I don’t know how.
So, yeah, my dating life hasn’t been all that great. I always tended to be in a relationship or the all too familiar situation of ‘talking’ to someone, but no real dates. The dates I have managed to snag definitely were not award-winning. I once went on a date with someone who doesn’t like cheese for goodness sake. I mean, that’s a nightmare in and of itself.
There was also this other time where the guy I was on a date with loved cheese, but the way he ate queso was a sin. He took the chip, dipped it in the bowl of queso we were sharing, and sucked the cheese off the chip. He then proceeded to dip that same chip back into the bowl of queso. I asked him why he did that and he told me, ‘I like the cheese. I don’t like the chip.” At least he liked cheese.
The first long date I can think of was with that high school best friend I tried to date the summer between high school and college. He was also the same one who ghosted and then came back to life like nothing happened. I’ll call him zombie here because I’m kind of nice and kind of don’t want to get sued.
Anyway, we went to dinner at Chili’s. The date itself went pretty well. We always had a good time and were comfortable with each other. Complete goofballs. I’d known Zombie for about ten years at this point in our lives. We weren’t official yet, but we were headed in that direction.
The food had been taken away from the table and the bill had been paid. Zombie said he needed to use the restroom before we left, so he got up from the table and I played a game of Snake on my flip phone until he returned. I already told you how old I was. I’m not that old, I swear. Technology has just progressed . . . a lot.
I had played probably three games of Snake, when I realized Zombie still wasn’t back. I started to look around the room and couldn’t find him. The wait staff kept passing by our table, I guess wondering why I hadn’t left yet; my date was clearly gone. I figured they thought he had either ditched me or I was waiting on date number two for the evening.
I thought maybe the food had upset his stomach and he needed some time in the restroom, so I played another game on my phone. Afterwards, when Zombie still hadn’t returned, I started to get worried. I grabbed onto the arm of one of the waiters and told him my date had gone to the restroom and hadn’t come back
“Can you please go check on him and make sure nothing happened?”
The waiter looked at me as if I had just asked the most outrageous question in the world. I mean maybe a grown man going to check on another grown man was a weird thing to do, but I didn’t care.
“What’s he look like?” he asked.
“He’s tall, dark, and handsome.” I smiled at the waiter.
He just stared back at me without saying a word.
Trying to do better in my description, I continued, “I’m serious. He’s 6’7. He’s black. And he’s good-looking. Can’t miss him.”
The waiter shook his head. “Sure. I’ll be right back,” he said.
A few moments later, the waiter returned, but there was no giant trailing behind him. “I’m sorry, ma’am. There was no one in there.”
The corner of my lip lifted slightly. “Okay, thanks for checking.”
Before he walked off, the waiter looked at me with sad eyes. Those eyes that said ‘Damn. That asshole must have climbed out of the bathroom window and left this poor girl all alone.’
Honestly, that’s what I thought. I mean, how could I have missed a gangly teenager who’s six foot seven go out the front door?
With my pride barely hanging on and tears being forced to stay out of my eyes, I walked out of Chili’s and toward my car.
Remember how I wished I could insert a straight face emoji into the text? Yeah. I need one here too.
When I walked to my car, who was leaning against the passenger side? Zombie. I just stared at him without saying a word. He put his phone in his pocket and looked back at me.
“What?” he asked with a goofy grin on his face.
“Where did you go? It’s been thirty minutes. I was worried about you.”
“I couldn’t find you.”
“I was literally at the table we ate at.” I crossed my arms.
“I couldn’t find the table.”
Straight face emoji. Right here.
The second longest date I’ve been on was one I went on with a guy from Plenty of Fish. It was some time after I graduated from college and after the relationshit I was in ended. I’ll call this guy Fish.
I had joined Plenty of Fish a few months after I became single. I was ready to mingle. Bet you haven’t heard that one before. This was before Tinder was a thing. Like I’ve promised you, I’m not that old.
After speaking with a few guys on POF, I came in contact with Fish. He was attractive and he had a great smile. His skin was dark chocolatey and smooth and he was so nice. We talked on the phone a number of times. He made me laugh and I got those little butterflies in my stomach every time his name popped up on my phone.
One day, he finally asked if he could take me on a date and meet me in person. I told him I would love that and we planned to go to a restaurant that was in between both of our homes. He had an apartment in Austell and I was living in Dallas.
My sister and her boyfriend at the time insisted on driving me. They said they would be close by in case anything happened and that way I could have a drink or two to loosen me up if things were awkward.
Fish and I agreed on a time and after taking hours to put on the perfect outfit and get my makeup just right, I hopped in my sister’s car. It took us about twenty minutes to get there and when we arrived, I sent Fish a text to let him know I was there. I didn’t know what kind of car he drove, so I couldn’t point him out.
He text back not too long after and said he was running late. I can’t remember exactly what the reasoning on his tardiness was because something more awful happened once he finally arrived and we got inside.
Fish finally showed up after I waited for at least half an hour. The whole sitting around for thirty minutes thing seems to be a pattern for me. Anyway, we walked inside and were seated at a booth. Fish was even more attractive in person. I’ve got a thing for teeth and his were perfect. They were straight and pearly white and thinking about his smile still gets me. You can add a word to the end of that sentence if you want to. Insert shoulder shrug emoji.
The date itself went well. We laughed and had a lot to talk about. It was my first time meeting him, but there wasn’t an awkward moment at all. That is, until we finished eating. That awful thing I mentioned? That thing worse than making me wait for half an hour? It’s about to happen.
“I want to come sit next to you,” he said with that gorgeous grin plastered on his face.
“Oh no.” I laughed.
“What you mean, ‘oh no’?”
“I can’t stand when people sit on the same side in a booth.”
“Really?” he asked. “Why?”
I shrugged my shoulders. “I don’t know. I just think it’s weird. Every time I’ve seen it, it just creeps me out.”
Fish just stared at me from across the booth where he should have been, still smiling.
“Besides,” I continued, “I can’t look at you while we talk if you’re sitting next to me.”
“Oh, come on. Let me come over there.”
We were both smiling real hard at this point. Seriously, just having a staring contest. I don’t know if he thought I was joking or not, but Fish got up and walked over to my side of booth. And then he sat down. The next thirty minutes of the date were awkward as hell and I definitely ordered that second drink. It was the longest thirty minutes of my life. Even longer than the thirty minutes I sat waiting on Fish and the thirty minutes I spent wondering how a six foot seven male fell in the toilet.
The last longest date of my life happened about a year ago. I’ve only been on three other dates since then. I lurv one of the guys, but it hasn’t gone anywhere yet. One of them was the chip, dip, suck, repeat. The other was a guy I met on some dating site that ended with an awkward picture at the end of an escape room. None of those dates were really that bad or too long or going to be a part of this story.
So, this other date . . . I met him on Tinder. See, now I’m more hip and relatable. I’m twenty-seven. I swear. We texted back and forth for weeks before we finally decided to meet up. Now, I told you I’m a stickler for teeth. In his Tinder profile pictures, his teeth looked pretty good. Not anything like Fish’s, but not terrible at all. However, there was something about them that just didn’t seem right. And this is just purely my own opinion.
Anyway, we eventually began following each other on Instagram. I finally got a better look at his teeth. Definitely, not perfect, but they were white and he, like Fish, had a great personality. We got along great and never seemed to run out of topics to text back and forth about.
After the few weeks of texting, we decided to meet. We both liked beer and chose a local brewery to meet up. As I was getting ready . . . oh shoot, I haven’t named this one. I’ll call him Cook. He told me he was a cook at a nice local restaurant, so that makes sense . . . Cook called me. We had never actually talked on the phone, only texted, so this was the first time I was hearing his voice. It was nice.
“Hey,” he said.
“Hey, what’s up?”
“What are you doing?” he asked.
“Just getting ready. I’ll probably be a few minutes late. I hope that’s okay.”
“Oh yeah, that’s totally fine. I told you I didn’t have a car, right?”
I would have definitely remembered that. I’ve dated way too many people without cars. It seems to always happen to me. I thought I had broken that habit, so if someone had told me they didn’t have a car, it would have stuck.
“Nope. You didn’t.”
There was a long silence. I guess he was waiting for me to tell him I’d come pick him up and take him to our date. He was going to have to keep waiting because it wasn’t going to happen. I’d never met him before. There was no way he was getting in my car before then.
“Oh. Okay. Well I’m gonna take the bus and the next one that gets here will make me about ten minutes late.”
“Okay, that works. I’ll see you in a bit.”
After I got ready, I got in my car and drove to the brewery. Between my house and the place, I got a text message and a phone call asking where I was. I wasn’t later than we had already discussed and it was raining outside, so slower drivers . . . there were red flags all over this date and it hadn’t even started.
When I arrived at the brewery, Cook was sitting at one of the high top bars that faced outside. I walked up to him and gave him a hug. That’s when I noticed his teeth. They were white, but they were also brown and green. He was nice though, remember. And I’m nice enough where I’m not going to just walk out of the date because of someone’s teeth. Or the fact that he didn’t have a car and expected me to pick him up mere minutes before our date was supposed to start. Or the fact that he appeared to be slightly impatient. But I digress.
We walked over to the bar where brews were being served. Cook already had a beer, but walked over with me. I ordered a flight and then handed my card over to the bartender. Now, I’m not expecting my stuff to be paid for, I can afford my own shit, but on a first date, at least argue with me about who’s paying. It also wouldn’t have been a problem at all if when we sat down, Cook didn’t take one of those beers off of my flight and start drinking it. Put that damn straight face emoji right here.
The conversation was pretty good. It wasn’t as great as I thought it would have been after our texting conversations, but this was real life. And I was pretty salty as I watched him take sips of that beer in between words.
The date was dwindling down after what felt like forever. I got up off of the stool and started to put my raincoat on. Cook stood up too and stared at me. I knew what was coming next and I interjected before he could give me a sob story about having to wait for the bus in the dark and in the rain.
“Do you need a ride?” I muttered.
The guy seemed pretty harmless and I was over ninety percent sure I could take him if he tried some shit. And I’m nice, remember?
His eyes lit up. “Yeah. That would be great.”
As we were driving to his place, he asked if I could stop at the grocery store. You know what needs to be inserted here.
“I just need to grab a couple of things.”
I sighed. “Okay.”
We stopped at the grocery store and he grabbed what he needed to cook dinner. All the while, trying to hold my hand and put his arm around my waist.
After he paid for the food, we got back in the car and he directed me to his apartment. He tried to kiss me goodbye and I couldn’t do it. I just couldn’t do it. I could not take one for the team. I could not fake it. I was exhausted. The date had drained me. So, I lied. I leaned away and I lied.
“I don’t kiss on the first date.”
I’ve done a lot more than kiss on a first date, cause we grown. That was a play on something Drake once said. Name that song.
I got home and took off my boots and collapsed on the floor. My mind began wondering how my dating life had become so bad. When did it become such a joke? Hey, you ever heard that one about the zombie, the fish, and the cook who walk into a bar?
originally published by the author (Shay Shay) on the blog, Solely Living