Discoveries Through Dating – Online and Otherwise

I have attempted to rewrite this article about my experiences with online dating a couple of times. The first draft sounded like a how-to, which felt dishonest because I haven’t been particularly successful in online dating or dating in general. The second draft was an attempt to be comical because of the plethora of ridiculous experiences I have had. However, this draft started to sound bitter. Noticing the difference between what I attempted to write and the actual tone of the writing allowed me to step back and evaluate.

I couldn’t ignore the feeling that I was avoiding something bigger and truer about my experiences. Did I feel bitter? As I came to realize the reality of my circumstances, I felt my back slump and I could only acknowledge what I had been fighting for so long- I was bitter, and felt defeated. I know this sounds dramatic, but I’ve dated a lot, with a relentless effort to find someone significant. Test-tasting everyone’s advice about dating and rarely turning off my search for the next potential partner was exhausting, and I came to realize that the bitterness stemmed from two areas.

First, was that all my efforts, worries, and work to have a symbol that I was lovable through having someone else in my life came to nothing. Second, was that I dealt with a lot of issues from the men I dated. Issues that weren’t mine to deal with, and so boundaries were often fuzzy. However, another feeling rose to the surface- thankfulness.

The Wonder Years

You see, I was that girl who had a crush on one guy or another throughout high school. When I was over with one crush I would intentionally search for another. It wasn’t so much that I liked a ton of guys at the same time. I was monogamous with even my crushes. I didn’t even like these guys’ characters or want to date them, but I was obsessed with liking guys (like most teenage girls are). Obsessed, I suspect, because I was bored in a small town. I had almost crushed on every guy in my year by the time I graduated high school.

It wasn’t the cute crushing either, where the girl blushes and tries to get the guys attention by smiling all the time. It was the perpetually embarrassing kind. I would blurt out inappropriate things or tell everyone how I had held my crushes hand during community prayer. Like everyone else, I was eternally grateful when high school was over. My crushes during my high school years never developed into anything. I avoided actually dating because it was a world I didn’t fully understand. And my weirdness around guys didn’t really help things.


It wasn’t until I was 21 years old that I had my first date. I know, a full three years later and still no date. To be fair, as much as I was weird, I was also a little petrified. A deer caught in the headlights to only bolt at the last second- which happened a few too many times- until my date on a train with a guy named Dave. The only reason this even happened was because I never thought that the people I would meet during this ride were going to be anything significant. And the train was moving, it’s not like I could have gone anywhere. He made his interest known and I went a little crazy. But just a little. Not psycho or anything, just borderline obsessive. I thought: this is my chance. He’s educated, good-looking, has strong values, and he rides horses like a cowboy! It had to work. But the relationship didn’t and couldn’t have worked. He lived in Montreal and I lived in Winnipeg. Yet, I couldn’t get past the fact that someone that awesome would like me, and thought I need to seize this opportunity the best I could.

That first date led to more dates with other guys- a lot of other guys. I was living in Winnipeg at the time, a place where (unlike Vancouver or Victoria) men actually ask random girls out on dates. I didn’t need online dating. Almost every weekend I was on a new date with a new guy. I had plenty of guy friends who could have been potentials. It was overwhelming, but I soaked in the attention. It was something I had never had in my life, not because I wasn’t beautiful before, but because I had “I’m too insecure to date” written on my forehead. I ended up dating a guy for three weeks knowing after the first date that he wasn’t a keeper. There was something comforting about knowing it wasn’t going to last with him. I finished things when it got a little too drama-filled. After the breakup, it was the first time I was unmotivated to date or even have a crush. I didn’t think about dating for three months and was quite relaxed about it all. But of course, things change…

The Beginning of Online Dating


On a chill night like any other, I was messaging a friend on Facebook and she asked if I would join an online dating site with her called PlentyOfFish. I had a couple of beers and was feeling good about dating again, so I said yes. Well, the first guy I talked to ended up turning into my first boyfriend, John.

Before this though, I was toying with the idea of moving from Winnipeg and heading west to BC. Then I met John and I thought my plans could change because of this really great guy. We had a lot in common and it was going really well. However, after three weeks of dating, he felt like things were moving too fast (and to be fair, it was). We had already started going to family functions only after two weeks of dating. This brought up the conversation of how to define the relationship, which we did very differently. When things ended, I decided I would move on and head west. Oh, but before I could leave he had to confess that he was sorry and that he didn’t know how to make it right. Remember, I was smitten with this guy. I really didn’t know what to do. I was accepted to UVic and the U-Haul was booked. So I moved on the contingency that if it went well long distance I would move back to date him – of course, unrealistically romantic. After his visit to Vancouver I ended things, realizing it was too hard.

Lesson: Sometimes timing, living authentically and a person’s life journey just doesn’t allow for something to begin for two people.

I Can Laugh About It Now…

There was a brief time when life was crazy after this. Not only did I feel the loss of a relationship, but the move to the west was harder than I thought. I had a family made of friends in Winnipeg and I left that community behind. The West Coast can be incredibly lonely. It’s almost as though people know how to have strong deep relationships here, but they don’t know how to meet people. Or simply don’t want to. I know someone who has a tattoo that says, “I can laugh about it now, but at the time it was terrible,” that truly sums up my life during this time. And yes, I know it’s from a Smiths song.

Um, You Have Something on Your Face

After the time of crazy, I spent an entire year with “f%#* off” written in 72-point bold font in German graphics on my forehead.


I couldn’t rub it off and I didn’t want to. I didn’t get asked out or even hit on. I spent that time either with friends or alone. I loved being by myself and finding out what I liked and who I was. I decided to start eating popcorn with a spoon and reading more. I didn’t watch sports, because I didn’t pretend to like sports like I had with previous boyfriends. It was nice not pretending to be interested in something I wasn’t. I didn’t dress sexy to get attention. I dressed comfortably and confidently. I went to the cafe to read and drink coffee by myself. When a friend couldn’t come to the movies with me, I went by myself. I loved it.

Back in the Game!

By the end of the year I felt like it was time to put my type-A pants on again and make a plan to meet new guys. This time though I was going to be careful, wise, and picky. I would talk to guys longer on the Internet before meeting them. If a connection was made but then I lost interest, I would give them enough respect to let them know I was no longer interested. I named the things I wanted in a relationship and the deal breakers. There are some things I just know I would totally lose trust in a relationship over, even though I wouldn’t judge a friend going and doing the same thing. I’m not sure why this paradox happens, but for some reason the things you look for in a partner are not the same as for what you look for in a friend.

Sunny and the Other Stars

Then came Sunny – who lived far away in another city. He fit nicely and, realizing how much I liked being single, I wasn’t obsessive. I liked the balance. At this point I still wasn’t used to being in a relationship. I was knowledgeable about the chase, but not the collaboration part. He ended things and I was taken back. I want to say I was devastated but I really wasn’t. The year of having “f’ off” on my forehead taught me that I was happy to be single, too. What I was feeling was confusion about why he broke it off. The relationship was going so well and even though it was hard, it felt good. To this day, I still don’t fully understand and I used to get incredibly frustrated with this until I remember what it was like falling for a guy I couldn’t regularly hug or see because it was hard for him to travel.

Lesson: Sometimes, the best fitting guys just don’t live close enough. If we had lived close enough I’m not sure if things would have worked out, but I’m choosing not to play that mind game.

After Sunny, I casually dated a few guys just because they made for an interesting story. One story was about a Christian girl who dated a liberal Muslim man. Another, was a logical woman dating an idealistic poet. This may make me sound shallow, but I promise you that these guys did grab my attention in meaningful ways. The Muslim guy, let’s name him Bob, had similar views on religion to mine. And the poet, lets name him Francois, was downright adorable with crisp blue eyes and a feminist heart of gold. But these men fell to the sides of my path as they moved on to the center of their own paths.

The Biggest Lesson of Them All

Last summer, I moved to Vancouver from Victoria and felt alone once again. I had moved to Vancouver to find a job and a boyfriend. I knew I moved to Vancouver to find a job, but I hadn’t acknowledged how much the move was about actually finding someone. Victoria is filled with women and I’m just not a lesbian. As much as I am ultimately happy being single, two facts still exist. One, I do still want someone in my life. Two, I’m type A and am focused on my goals. So once again, I went on a lot of dates.

And this is just how type A I am; before I moved to Vancouver I had multiple dates lined up. I met a Christian guy who was conflicted between the man he was and the man he thought he was suppose to be. I met another guy who lied about his height. My vertically challenged date proceeded to jump beside me as he measured how tall I was in comparison, while asking me if I wear heels often. There were also other dates I had with men that would only disgrace the gender, which I don’t think it deserves.  

From the time I moved to Vancouver in June to the end of July I became bitter and exhausted. This just so happened to be around the time I was asked to write about my experiences with online dating. I wanted to scream in life’s face and tell it that I was single but not for a lack of trying. I was sick of meeting men that lied on their online profiles (# 1 lie I’ve encountered is about height). I was fed-up with men thinking I wanted sex on the first date or not caring about what I wanted. And though I know it’s hard to make conversation with a complete stranger, I was tired of making the conversation move along by myself. I was done with all of it. Every relationship that I spoke about here, along with the other ones I didn’t mention, felt up against my back or right up in my face. I felt suffocated and angry. But I wouldn’t take any of it back. I wouldn’t take back the attempts or the breakups.


As I’m writing this now, I can feel the tension between the frustration and thankfulness for what has brought me to this place in my life – to this place in me. I like how the journey has shaped me and given me distinction.

Another tension remains in me and it’s between wanting someone of significance and realizing that a lot of how my story goes is out of my hands. I know as my life continues it will be harder to begin a family. This saddens me and at times makes me want my type A dating pants on again. And yet, I find myself living one day at a time, enjoying life too much to bustle. Thinking that it will come if it comes.

Recently though, I did meet someone. He’s been really nice and thoughtful. There’ve been eight dates so far, even though I know he thinks there has been more (JD, passing you on the street or driving me to the ferry doesn’t count as a date). But even if this relationship fades to the side of my path because we are following the centre of our own paths, I have learned to be cautious. With scars and burns I learned to cover my heart and take stock. To reflect and take time to contemplate why I am in this or that relationship. JD may be humanly wonderful, but he is not worth losing my mind over.

Lesson: Romantic relationships are important, but they are not worth insanity.


The bitterness lead me to independence – the feeling of knowing where I end and they begin. Well, actually bitterness and counselling have given me this. But this point of the story is about the good coming from the bad. I believe what Brene Brown says about vulnerability and shame, and the influence those have in our relationships. It’s incredibly scary to be single and wonder if life will always be this way – lonely and missing that significant other. But whether you use online dating or the regular kind, it’s simply another mode to learn about yourself. Any relationship, but more so romantic relationships, tell us deep things about ourselves. To discover something we didn’t know about ourselves.


Looking over this article I realize I have described some difficult areas of my life and old ways I’m not entirely proud to have grown from. I decided there was value in telling you where I came from (i.e. obsessed with guys) to show that inner motives can change. And to show that progress isn’t seen in getting the guy or girl. It’s not about reaching the goal of a relationship, but how the relationships in our lives reflect where we have come from, where we are now and direct us to where we need to go. Whether people share our path for a little while or a long while, there is gratitude that they walked with us for a time.

To sum up my experience with online dating: it works sometimes, but most of the times it doesn’t – kind of like regular dating.

The writer of this post has chosen to remain ANONYMOUS.

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