Best And Worst Dates I’ve Been On

I think it’s safe for me to say, that the best dates I’ve been on have all been with Ray. Even our very first date was one of the best dates I’ve been on. We matched on tinder, talked, and he said we should go out for drinks. When I told him I was all for it, but I lived an hour away, he was still game. He drove up to see me, and he took me out for dinner and a couple drinks. And it was just… nice. We just talked and there was no expectations.

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I didn’t do this on purpose, but I remember I went to the restroom and when I came back out he had already taken care of the bill. And when I saw he left a decent tip for the waitress, too, I was impressed. It was rainy that day, but we got a reprieve when we left the restaurant, so we walked around for a bit, and I took him through campus. We were walking towards it when an old lady and her husband drove up to us and asked us for directions. I’m terrible with  directions, and Ray isn’t familiar with the area, so we were no help, and I felt bad. But they were starting to get cars behind them.

At the end of the date, we were walking back to his car, and he kissed me. And said that he wanted to make it work. That to him, he wanted to see where this could go. It was raining so he drove me home. But, it was probably one of the best dates I’ve ever been on. Because it was getting to know each other in all that awkwardness, but somehow it wasn’t too awkward. And, almost 6 months later, we’re still making it work. To me that means everything. There’s this fine line where I’m not sure what counts as a date and what doesn’t. Because we went on a trip together, but does that mean those two days were one date? Or just when we went out to eat? When I come to visit and we hang out, it’s not really a date. Otherwise I’d say it’s only gone up from the first date! I don’t think our shopping trips to Aldi counts as a date either.

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Now, my worst date. There is one that really sticks out to me, and it was also someone I met online through an app. I was trying out Plenty Of Fish, because I’d seen it recommended and I was needing a break from Tinder. I’d tried OkCupid first, but the choices were really limited and I deleted the app. So I matched with a lot of guys on POF, to the point it was actually overbearing. I was getting messages every minute at one point, and it was just too much. But I did talk to a couple of guys off of there, and one of them was this guy, let’s call him Bry. He seemed nice, also in Pittsburgh, but he worked in I.T. and seemed to have his shit together.  I remember, he asked if I wanted to meet up, and I agreed to it. 

I think it may have been sometime in February. He drove up to see me, and we had plans to go to dinner. Let me start with, on POF there’s a section where you can input your height and status and stuff like that. I completely overlooked the fact that this guy is 6’5″. I’m 5’0″, so when I saw him in person, I felt super small and overshadowed. My head didn’t even reach his chest. That was how this date started.

We went out to eat uptown – he was a little familiar with my area due to having local friends. Well, it was a Saturday night, sometime around 6 or 7. So… it was busy. And the place we went to, it was noisy. Not very good for a first date at all. I mean, we talked, but it was really awkward. The entire time I just felt so out of place. Honestly, I was happy when we went to leave, but again, as soon as we stood up, I was very aware of the height difference between us. 

Don’t get me wrong, this guy was nice. He really was. But, it just wasn’t there. It was all wrong, and way too awkward. We talked for a little while after the date, but it didn’t lead anywhere and we never met up again. Eventually, we just stopped talking completely. I wanna say this was towards the beginning of 2016, so it was almost two years ago. 

I’ve definitely had a few good dates, and some really awkward ones. This one was definitely the most awkward, and stood out the most. I’m definitely not one to judge based on appearance (I mean, I have to find you somewhat attractive, but my tastes are different than my friends), but I came to the conclusion after that date, that there is, indeed, such a thing as too tall for a short girl. At least for me. 6’0″ is tall to me, and 6’5″ was just gigantic next to me. There’s a tall girl out there who’d love that, I really think so. 

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November Writing Challenge #14

17 thoughts on “Best And Worst Dates I’ve Been On”

  1. Aha I can totally imagine how weird it could feel to date someone way taller than you – how do you hug? How on earth am I going to kiss you like I cant carry around a ladder all the time. That said, I LOVE tall guys – they just also have to be somewhat strong so they can lift me up to their level xx

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    1. It was so awkward! And I had those same thoughts! Like even on my top toes I wouldn’t have been able to reach his face 😅 I love tall guys! Just… there’s a thing as too tall for me hahaha. But yes I agree!!


  2. Aww your first date with Ray is so cute!!!
    Haha having too much of a height difference is a thing. My parents have it and it is a big joke in our family especially cause my sister and I went on my dad thankfully and are a lot taller than mum

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  3. We are the same height! I wouldn’t want to date a super tall guy either because it would just feel so off-balance to me. I’ve never used any dating apps because I know that would eventually lead to them wanting to meet and my anxiety always causes me to bail out. I’ve had guys through facebook chat with me and want to meet. I am considering meeting one of them, but I keep putting it off because of my anxiety. This is why I’ve been single for four years. lol

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    1. Ohh nice! 🙂 and that’s exactly how I felt when I went on that date. I used to have a lot of anxiety about meeting guys – I bailed on so many, or met someone once but made excuses not to meet again. I went through a cycle of that before finally being okay with it. And I still get nerves meeting someone for the first time! The best part is to talk to someone for awhile before meeting, but a lot of guys don’t seem to want to talk for awhile, they talk better in person. I would say it’s good to push your boundaries – go on a date! Make it at a public place if you’re uncomfortable meeting someone you don’t know. I’ve never met anyone randomly through Facebook – although some have tried lol. I wouldn’t do anything you’re not comfortable with! Anxiety can be so hard!

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  4. I went on a super awkward date once, I was just super uncomfortable the whole time. We didn’t really even connect at all but he didn’t stop texting me for months. At least the tall guy got the hint lol! I’m so happy for you and Ray! What a sweet first date. ❤

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    1. Ohh gosh that’s the worst! He must’ve been into you but didn’t get the hint, that’s even worse! Bad enough the date didn’t go well lol. And true! He was nice but it just was never going to go anywhere. He didn’t try to meet up with me again either, so he may have felt the same lol! And awww thanks, it was ☺️

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  5. Aww, Ray sounds like a great guy with the bill and tip story!! I’m impressed as well. I always see to it how someone treats a waiter, waitress, janitor, et al whenever I’m getting to know them because I feel like it speaks volumes.

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