My Awkward Dating Experiences Part 1

Story time!

I was randomly thinking about this the other day, and I decided I had to share it out. About 2 years ago, right around the time I really started dating, I had probably one of the most awkward experience with a guy. I talked a bit about what was going on at the time in my other post “How I’ve Changed in the Last 2 Years” .


To reiterate, though, around this time I had been seeing this guy named Nate. He didn’t want to be seriously involved, so I was fine with being in an unlabeled relationship – for a bit. We’d probably been right around our 3 month mark. I remember I first started to really have doubts. Honestly, I wanted more from him. All we did was hang out and have sex and maybe watch some Netflix or TV. That was our entire “relationship.”

There was one night I came over, and I remember we were sitting on the couch wrapped in a blanket. His roommates were sitting on the other one. And we were watching the newest episode of American Horror Story: Hotel. I just remember that the entire time Nate and I were sitting there, he was either tuned into the show (which was fine) or he was checking sports scores on his phone. His roommate was having more conversation with me than what Nate was. It made me feel so out of place.


When I left that night, I was talking to my best friend Dayna about it, and she had been trying to set me up with this friend of her boyfriend’s. “He’s really cute and nice, you’d like him.” So even though I was still seeing Nate, I decided there wasn’t any harm in really meeting this guy. His name was Vaughn.

The first time I met him, I agreed that he was cute – but on the younger side. I was 22, and he wasn’t even 21 yet. Pushing that aside, I decided to give him a chance. For my friend who was pushing so hard for me to be done with Nate and be in a good relationship.

That night we met, the four of us (Vaughn and I, and Dayna and her boyfriend (at the time) Joey). It was one of the reasons I agreed to go – with Dayna and Joey around it helped ease the awkwardness. Because let me tell you, Vaughn is one of the most shy guys I have ever met. While he seemed interested, he barely conversed with me. But on the ride back to dropping me off, he kept trying to grab my hand, and I went with it – because why not. We exchanged numbers and started talking.


It started off fine, but the more we talked, the more boring our conversations got. Let me explain something: I live in a town surrounded by areas we sometimes refer to as “hick town.” Because it’s basically countryside and farming and rednecks. Joey owns a big local farm around here (which was why it was so odd for Day to be with Joey, she’s such a city girl). So Joey has farmer friends. Vaughn was one of them. His family owned pigs. And he loved to talk about those pigs. Probably because it’s all he knew.

While that’s fine, underneath it all, the two of us had nothing in common at all. And my inner grammar nazi could not take him seriously when he consistently spelled “been” (like “how have you been?”) as “bin,” and “warm” (as in, “are you warm”) as “worm.” It wasn’t autocorrect because he spelled these words like that every single time. That’s not the funny part though. He had asked me if I wanted to come over and watch him work on his truck. Like a first date. Come over and watch him work on his truck... What kind of date is that? When I told Dayna about it she about tripped over. We barely know each other, and to him that’s fun? He listened to country music at that, and I can’t stomach 99% of country. First dates are more “let’s go watch a movie” or “let’s grab a bite to eat.” Not “want to come watch me work on my truck?”


We were on our third meeting (I think), and I remember we were over at Joey’s (the four of us). Vaughn barely spoke a single word to me that night. He sat on the opposite couch and talked with Joey about guns. The two of them left for about a half hour, and when they came back they both had $20 lottery tickets for us. Which I didn’t expect at all, but they both have decent money. I hit $100 that day (which was the last time I ever won anything on a scratch off). But still, Vaughn barely spoke to me. And his shyness was getting to be a bit too much. I’m shy – or well I used to be, but I will have a conversation or start one because I had awkward silences. Dayna and Joey were both talkative so that had helped. And we were drinking, so Day talked Vaughn into giving me a ride back.

Here’s where it gets awkward. The entire ride (about 30 minutes I want to say) was silent. Oh I tried. I even made attempts about mentioning the deer we saw (it was hunting season and I knew he hunted). He had country music on the radio (cringe worthy to me). But I couldn’t get him to talk. His answers were short. So we rode in silence. When we reached my house, he leaned over like he was going to hug me, and I kind of was whatever at that point, so I went to give him a hug. And he KISSED me. Like what part of that ride did he think I wanted that? I was taken aback, and I kind of rushed to end things and left. And I texted Dayna as soon as I got inside, and she was freaking out with me. He barely spoke to me that night, but kissing me was okay? I was completely confused.


Needless to say, I didn’t attempt to go out with him again. He tried a number of times to get me to go out to dinner, but it was too awkward for me. We had nothing in common, he couldn’t hold a conversation, and it was just…boring. Day kept trying to get me to give him another shot over and over, and I just couldn’t. Especially after that kiss. It through me off. So I backed off from him.

Sadly, a few months later when I was over, and Vaughn was there, he attempted to restart conversation with me. Through Snapchat. So instead of texting me “Hi, how’s it going?” he would send me a picture of his face on Snapchat and say “Hi.” After several of the same conversations he sends me a message on there saying, “So when are you going to let me take you out to dinner.” I replied back to him that I wasn’t looking for anything at the time (I had ended things with Nate about a month before). He snapped me back “K.” and that was the last I ever heard from him.


Maybe I didn’t go about this situation the best, but it was one of the most awkward dating experiences I’ve ever had. I could never be with someone I have nothing in common with. And he couldn’t hold a conversation – even when I would try and mix it up to make the conversation a little more interesting. Just was not happening at all.

4 thoughts on “My Awkward Dating Experiences Part 1”

  1. Omg, hahaha I literally laughed out loud when you said you couldn’t handle him spelling “bin” and “worm”, that would make me mad, too!

    I can’t believe he kissed you after a completely silent car ride, that’s so awkward! He just sounds so weird! I’m glad you went with your gut and just decided to back away from him, haha.

    Liked by 1 person

    1. Haha ohh it drove me crazy 😂 and he spelled it that way every time so it was intentional. I just couldn’t take him seriously when he would say “I like it better when it’s worm.”

      And right? It was incredibly awkward, and he was! I’m happy I did, too, haha. It never would have worked out

      Liked by 1 person

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