Life

The most awkward first dates I’ve ever had

By  | 

awkward first dates

So maybe you’ve been through some awkward first dates. I mean we all have, right? No one’s ever totally smooth, as much as we might wish we were. So just remember you’re not alone. All of us, including me, have had some really awkward first dates.

And in fact, I’d go so far as to say that my awkward first dates might be as awkward as they come. So today, for National Awkward Moments Day, let’s take a fun little stroll down awkward memory lane and talk about some the most awkward first dates I’ve ever had.

My Awkward First Dates

So as far as awkward first dates go, these are my personal submissions. I’ll just refer to the girl by one letter, just to avoid any possibility that they will be embarrassed by reading about me sharing my personal feelings of embarrassment.

Never date a musician

So for the first of these awkward first dates, let me set the scene a little bit. The girl, S, was a musician who was moving to town from New York in the hopes of pursuing a career as a singer/songwriter. So I took the opportunity to ask her out on a date since she was going to be new in town.

But, what I wasn’t aware of is that apparently being a musician doesn’t leave you with a lot of free time. So the only time she had to spare was after a show she was performing in some tiny bar. She invited me to come watch and meet her after.

So after ignoring what should have been the first red flag, I agreed and dutifully showed up to offer some support. But after two hours of performing and occasionally coming over to my table to sip off a hard cider and exchange some pleasantries with me, S’s show was finally drawing to a close.

“Great,” I thought. Now she’ll have some time to spend with me. But just then two people who, I think ran an internet radio station (I’m not totally sure), showed up to invite her to some secondary function. So I ended up tagging along in the car while they complained all night about the music industry and talked about spreading the gospel for some reason (I don’t think it was even a Christian radio station). This should have been the second red flag.

Finally, we got back to her place after she dropped some hints that she wanted to spend time alone with me. But I blew it by asking if she was going to have any time to keep going out. She got a little defensive and I ended up leaving. This is the basic formula that would play out over the next two months before I finally realized it wasn’t meant to be.

Oh, this wasn’t a date

As awkward as that first date was, this second one is far worse. Mostly, because it turns out it actually wasn’t even a date.

C, as we will call this girl, was someone I met in college. I asked her out and got her phone number, and she seemed genuinely excited to go out. So, looking for something a little less formal, I invited her out with my friends and I for some karaoke.

Unfortunately, my friends started drinking a little early. By the end of the second song one of them was drunkenly chatting up a group of girls and two had gone missing. C and I went looking for them and found them sitting outside the bar. One of my friends was slapping the other into tears and trying to get him to punch him.

Not the kind of thing you want a date to turn into. Finally, we got them separated. C comforted the guy who was getting slapped while my friend doing the slapping asked me repeatedly to punch him. A little irritated, I gave him a light punch on the chin and he thanked me.

The evening died down and I said goodbye to C and drove my friends home in silence. At the second light the friend I had punched suddenly punched me in the back of the head for revenge. I pointed out he had asked me to punch him but he had forgotten by now.

I sent C a text saying I was sorry for how things went and asked if she wanted to go out again. It turns out she didn’t realize it was a date and wasn’t looking for a boyfriend. Her exact words were “no offense, but if I were, I’d be looking for a black guy.”

So yeah, not a great date.

Is that a dog?

I met this girl on the internet, Tinder specifically. So we met in a coffee shop and talked for a little while. After about ten to fifteen minutes, I realized she clearly had no interest in me. After all, if my previous dating experience has taught me anything, it’s when a girl isn’t interested.

So not knowing how to end the exchange gracefully, and wanted to not take up any more of her time, I started looking for an excuse to get outside so I could end things. I suddenly looked outside and said, “Oh, I think there’s a dog out there, let’s see if we can pet it.” Not really an elegant solution but it worked.

So naturally, she followed me outside, only to see there was no dog. I apologized and said I must have been mistaken, but that it was nice meeting her and I’ll see her around.

So I walked back to my car and drove home. That night I got a text from her saying she liked meeting me and wanted to see me again.

Long story short, we’ve been dating for two years.

So it just goes to show you, sometimes an awkward first date is the best kind. So tell us all about your awkward dates in the comments. Can you top mine? What’s the most awkward first date you’ve ever had.

Wyatt is a writer and your friend. You can follow him on Twitter @WyattRedd.