I like to think that Adventures in Dating is a pretty realistic series. Cat and I both do our best to be as real as possible and highlight not only the hilarious dating adventures we have experienced, but also the tougher ones.

Although most readers have come to love our series for the laughs it provides, we get the most response from our raw and real posts.

I was reflecting on what to write about today and what direction I wanted to take the post in. I began reflecting on my online dating adventures and was reminded of an experience that I had never touched on. It was the closest thing I had to a real relationship while navigating the online dating scene (other than finding my husband) and I think that’s why I never wrote about it. It was so close to being something and then it wasn’t.

It is that statement that describes what can be so soul crushing and heartbreaking about online dating. The online dating world operates in its own bubble where sometimes judgement can get clouded a little easier, hopes get higher a little quicker and events that wouldn’t normally get to us can be devastating.


Let me tell you about my heartbreaking online dating story: Graham was tall, cute, kind of shy and a hockey player. After a lot of chatting online we decided to meet for a date. Our first date was one of the best dates I ever had. We went for drinks and sat at the bar watching a hockey game. We ended up cheering for opposite teams and poked fun at each other the entire time. It felt like I knew him forever. We laughed so hard, until we cried, and drank way too much. After the date as we were walking to the subway station to go our separate ways he grabbed my hand. We stopped outside to say goodbye and he surprised me by kissing me. We kissed for a while (hey, I said we drank a lot, okay?). This was the first time I ever kissed on a first date. I left feeling excited and really hopeful.

After I found out his last name, I creeped him on Facebook and found out that he was mutual friends with Cat’s cousin. As it turns out, she knew of him and had even met him once.

Graham treated me like one of the guys (this should have been the first indicator things weren’t going to last). He called me knuckle head and other nicknames I thought were cute. On our fourth date he took me to his house and we ate dinner and watched a movie. During the movie, I tried to cuddle up to him, but he was distant. I tried kissing him and could tell he wasn’t into it. I asked him what was wrong and he admitted he wasn’t over his ex-girlfriend. They had broken up two weeks before we started dating. He admitted it wasn’t even him that created his online profile but one of his friends who was trying to help him move on.

I should have ended things there and I should have told Graham he needed time to work through his feelings, but I didn’t. I had finally found someone I liked and I decided that I would fix him myself. I had finally found a good guy  and I was not giving him up, even if he was caught up thinking about his ex.

We went on a few more dates and although they were fun, the spark was gone. However, it was the longest stretch of time I had spent with a guy since I started online dating. I didn’t want to give up that security blanket. I was living alone, away from family and friends, and he was virtually the only constant in my life other than my job. I held on when I should have left go.

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After seven dates, and three months, he dumped me. He said he wasn’t over his ex. He cried and explained to me that he was trying to replace her with me but it wasn’t working. I explained to him that I was trying to fill a void in my life with him. We were using each other to cope and to try and find some hope in a sometimes hopeless place (aka the online dating world).

I was heartbroken over something that was never really anything to begin with, but because it had the potential to be something it hurt. This was a hard lesson to learn but an experience that showed me how easy it is to get swept into the bubble of online dating. This is a world where I held onto something that I knew was going nowhere. I held onto it so tightly because it was all that separated me from being alone again. I knew things were hardly even good, but at least it was something. I spent my time with a guy who was thinking about another girl, but at least I was with someone. This is why online dating can be heartbreaking. Some of you may read this and not understand at all, and some of you are nodding your head so hard you look like a bobble head.

Last year, just around the time of my own wedding, Cat found out Graham had gotten married too. My heart was so full hearing this. It meant that we had both worked through what we needed to and we were both happy. Genuinely happy. Graham was one of the only guys I dated online that I look back on with happy feelings, even though it was such a dark time. In a way, we were there for each other and although we weren’t supposed to be together forever we were there for each other for that short time.

Have you ever stayed with someone even though you knew it wasn’t going to last?

Written by Tracey