How Weird Online Dating Can Get

Today was an all new high/low of online dating weirdness. First, my history of online dating so far.

I’ve met a person enthralled with her writing. I loved talking to her about it. I enjoyed hanging out with her. She met someone else but said we could be writing buddies, and I was okay with that.

Another time I started talks with a smoking hot international model. Who was in London to look for work. But got stranded due to a ticket issue. And wouldn’t be able to go on a date until she found a ticket back to the states. And she needed $850 from me to help her because all her financial information was wiped out. I figured on this one I was either getting a date with an international model or I was getting a good story. Well either way I was getting a good story.

I’ve met funeral home workers, teachers (a lot of teachers), entrepreneurs, nannies (favorite was a Brazilian aue pair), and many other professions. But tonight took the cake, and I’m a little torn on how to go about this.

I messaged someone. She was a blue, which means perfect match. She’s attractive, creative, looked fun, so I thought, heck yes, let’s do this. I expected no response. Out of ten messages sent out, I might get one back. We have three phases of Q&A before the open discussion. I rarely get past phase one. I’ve gotten to open discussion maybe five times in around seven months. You have the option to skip to open discussion, and though I’d prefer this, people seem to like the safety of that predestined net.

(While typing, this started playing. I started writing to the rhythm, getting even more worked up. It was great.)

So this someone I messaged wanted to talk straight with me. I thought, “This is fantastic!” We skipped all the fluff and just got straight to…. And then I read what she wrote. She was my prom date junior year of high school. It was awkward. We were set up by a mutual friend just trying to make sure everyone had a date. She was cute, don’t get me wrong, but mostly we just hung out with our other friends. She was a grade older than me. Through really awkward moments later, I was entirely written off, though at the time I didn’t care. I hadn’t given her a second thought. Now here she is. A blue match. Not only a blue match, but everything about her I would consider attractive.

My mind reeled. I’m a writer. This ends like a fairy tale. My prom date over ten years ago accidentally meets me on a dating site which says we’re perfect for each other? This is a sign. This is destiny. Obviously the script has been written. We step into this slowly, estranged at first, but with time we realize what we could have had that decade ago, all these wasted years and dates, and the stars align just right! How could this possibly go wrong? I will start conversation, it will be slow, but it will lead to something…. Oh, she messaged me.

“Good luck on eHarmony.”

What!? The fates conspire! They plot against me and my heart! This was the perfect story. The manuscript could not be more perfect. The heartbreak could not be more apparent. More feigned heartbreak just to make the moment right, and more towards the fact a perfect moment was allowed to spoil like this. Or is it?

So she asked how I’m doing after pointing out we were prom dates. I told her and asked how her art was. She said well, good luck on eHarmony. Is this a dead duck? Was I shot down? Or is this playing hard to get? Do I reach out? I have no idea what to do on this. Any suggestion on women would be great. Did I shoot myself in the foot ten years ago, an immature child incapable of comprehending what he had? Maybe more unsure. I’m just being overly dramatic. Anyway, is this something to go after, or do I just move on to the other unresponsive singles?

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13 responses to “How Weird Online Dating Can Get

  1. I think you could take what happened to you in this instance as a start of a story that you can turn into anything you want whether you contact her again or not. So the story is set – you just have to write the ending.

    As for contacting her again – if you like her, why not give it a shot? I mean, at the very least, you’ve reconnected with an old acquaintance and maybe you become friends or maybe not. Worst case scenario, she shoots you down. And that’s not the end of the world, so, why not?

    • What if it is the end of the world, though? What if there’s a trigger that under these circumstances…. Never mind. It is a really brilliant story idea, though. Alright, why not indeed. I’m just cowardly.

      • Umm… we just did Tough Mudder. Cowardly is no longer an option because we’re pretty invincible. So… buck up.

        (Also – write the story… maybe it could be part of the romance you’re writing… OH, that’s how you get the jealousy factor into it – she reconnects with her old high school fling while she’s sort of not really getting involved with the main guy and then it’s that “who does she choose” and the two guys sort of get jealous, etc., and sort of fight for her… it could work… maybe.)

  2. Hmmmm, perfect, yet a little closed minded? High school was another lifetime, unless you did something really shitty…. there was a guy I went to school with that always called me “saucer eyes” on the bus… I hated him… he tried to connect with me about a year ago… DENIED.

    • No. I didn’t make fun of her or anything. I haven’t had the guts yet to even reach out, so I’m not sure. It’s just weird. That crap doesn’t happen in real life. This is a novel moment. But yeah, good call on denying him.

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