Looking back at my past dates....

Post Reply New Topic

While I remain on a dating hiatus, I thought I would share my (quite interesting) history of the people I met through online dating. Most were onetime meet-ups, though others seemed like they had a chance of being successful. Since it wouldn't be appropriate to use names, I will describe each connection with a line that pretty much sums up the experience.

Let's begin.

The College Curiosity - Sometime in 2001/2002
This meet-up (which happened nearly a decade ago) came from my earliest experiments with online dating when I wasn't all that serious. In fact, we didn't even meet-up in a dating capacity and we only met up because we went to the same college. It didn't really lead to anything, though we did have a brief re-connection last year through POF (which also didn't lead to anything). I should also note that is the only online connection I've had prior to my asperger's diagnosis.

The Fellow Aspie - Summer 2009
This was my first proper online dating meet-up, which occurred nearly two years ago now. Our common ground was that we both had asperger's and we gave it a shot and met for coffee. I thought it went OK enough, but the combination of us living somewhat far away from each other (and the fact that she was not sure about meeting again) resulted in the end of the connection.

Raised Expectations - August/September 2009
This connection is the best example of the raised expectations that can come out through the communication phase. This girl spoke of the prospect of us dating like it was a certainty (i.e. using "when" instead of "if"). However, in the end, we only met once for coffee. We remained in contact for about a month or so until she updated her Facebook status saying she was in a relationship (with someone else) and that was that.

Twilight Fan - November 2009
I think of all my failed online connections, this was the one that angered me the most. So our first date was coffee, which went OK enough. I managed to get a second date out of her, by using her love of the Twilight series. Basically, the second date consisted of us going to New Moon together. She noticed that I was quite bored by the movie and shortly afterwards I found out she was with someone else (this is repeating trend). I was so angry afterwards (mostly because I wasted time to see a movie I didn't want to see).

The Closest I Ever Got - February-July 2010
This is simultaneously my most heartbreaking connection, as well the one that (in retrospect) I'm glad didn't result in a relationship. This connection had a promising start and I we actually had three dates within a short timespan. Afterwards things slowed down for a month before we met again to celebrate my recent birthday. In a bit of bad timing, I went on a previously booked trip to Scotland and Amsterdam with my sister in late May/early June. I tried getting together again with this girl one more time before leaving, but she didn't show up. I sent her a postcard while I was away and when I came back she congratulated me on my university graduation. We made an arrangement to get together, however she didn't respond when I later texted to confirm. Then came the "status update of death" (which I've come to dub a change in relationship status on Facebook) and I (very reluctantly) cut off connection with her.

Now for a brief explanation why (in retrospect) I'm glad this didn't work out. Essentially, I was in over my head with this connection. Not only was she a couple years older than me (not that big a deal on it's own), she also had some major issues. She was living at home alone with mother and had some financial difficulties (which was part of the reason why she didn't show up for that date before my trip). I'm sure whoever she ended up with was able to provide for her better than I could.

The WoW Geek - August 2010
This was a very brief connection which seemed too good to be true (and it turned out that it was). This girl lived fairly close to me, was also quite shy, and had similar interests to me (including being a World of Warcraft player). Before we met up for our first (and only date), we would talk on Skype while we both were playing the game. We would meet up to see a movie, which I thought went well, and we actually made plans to see another movie the next week, after I came home from the cottage for the August long weekend. I came home, and she immediately contacts me and says that she had been thinking and that she did not want to pursue a relationship. The salt in the wound was that the reason she did not want to date me was that she wanted to date someone less shy and more established in life (i.e. employed and living alone). I ended going to the movie planned for the second date alone....

The Walk - January 2011
This girl seemed to be also a good match for me. However, our one and only date consisted of getting a coffee and going for a walk. I realized this connection was over before we even said our goodbyes. She definitely seemed very skeptical of online dating and I had a feeling she was just trying anybody. When she said goodbye with a handshake instead of a hug, I knew that I was never going to see her again (which she confirmed with a message - being a little too nice about the rejection).

The Jays Fan - February 2011
As you might have noticed, instead of the "status update of death," I was now dating girls who actually cut things off. This girl was no different. The common ground we had was that we both big fans of the Toronto Blue Jays. We to see a movie, followed by a lengthy walk and coffee. A few days later (after no messages), she finally messaged me saying that she enjoyed getting together, but did not want to pursue anything with me.

Bad Luck - March/April 2011
It should be noted that all the above (except for the first) I've met through either PlentyofFish or Lavalife. This next girl (my last connection) was the only person I met so far via OKCupid. This one had so much promise and I attribute bad luck for it not really going anywhere. For our first date, we were going to go watch to St. Patrick's Day parade together. However, as luck would have it, she got sick with, what turned out to be, bronchitis and had to cancel. We kept in touch during her sickness and we probably exchanged hundreds of text messages between us. However, after a week or so, the texts began slowing down and I feared the dating window had passed. However, when we finally made arrangements to meet for brunch, my fears were diminished. We met up and (like a gentleman) I paid for the meal. I later wished I didn't pay because, aside from one reply saying that she enjoyed meeting up, I never heard from her again. She stopped replying to my texts and I eventually took the hint and cut things off. The sad thing was that this happened really close to my birthday and I sort of hoped that our second date would've involved doing something on the day. I actually waited until after my birthday had passed (and I received no messages from her) before finally pulling the plug.


It's definitely an interesting history, but at the same time it's frustrating that I've had so much failure in only two years. Hopefully, I'll eventually be able to bounce back and have some success.