Blog, Dating, Life

My Three Date Weekend: Introduction

Ideally, I try only to date one person at a time. There are people out there that can juggle several dates at once, but I never thought I could. Not only is it a logistic nightmare, but it also just doesn’t feel right to me. I know this is just an old hangup from some of the morals ingrained in me from childhood, but that’s how I feel. However, this weekend I didn’t just ignore this feeling, I threw it out a 12 story building, as I went out with three separate women. Here’s that story.

Recently, after the rejection of the pole dancer, I threw myself back into the online dating game. Usually, as a guy online dating, you send out 10 messages and are lucky to get 1 in return. I sent out 6 and got 6 replies. Most wouldn’t consider this a problem, but as I mentioned above, I try to only date one person at a time. What’s worse, each of these women seemed great on paper.

Over the course of a week, I got to know 3 pretty well while also rekindling conversation with a woman I had went on a date with a month ago, but who was too busy to see me at the time. The conversations all came to a head at the same point and I realized I needed to ask them out or they might lose interest.

The first girl, Kay, wanted to go out Thursday night, but cancelled the day before and wanted to reschedule to Saturday. She then wanted to shift Saturday to Friday, at which point, I was already making plans with 3 other women. Rescheduling once is okay, but rescheduling twice in 2 days is bit much. Homie don’t play like that. So I told her I was busy and that we’d figure things out later next week.

The second girl, Cee, is from out of town (an hour out from Toronto). She was going to be in the city for Fanexpo and had Friday night free, so I scheduled her for then and we decided to meet up and play it by ear. More on that date to come.

The third girl, Ming, is the one I rekindled things with. We had gone on a date a month prior (which I did not blog about) and had a really great time. We checked out this cute place called Light Cafe and shared a dessert. She was beautiful, smart, and fun, so I was really interested to see her again. She lives in the city, and was a bit of a priority in my mind, so we scheduled a Saturday brunch date at Smith Restaurant. More on that date to come.

The final girl, Ami, is also from out of town (40 minutes out from Toronto). She goes to school in Toronto and has a love for the musical Hamilton, which is an interest we share, so I scheduled grabbing some tea with her on Sunday afternoon. I had expected to have to travel to her, but she made things easy for me and came up to Toronto. Again, I’ll be making a separate post about that date too.

Each of these dates was unique, and the experience with each girl varied. I won’t get into spoilers, but the overall point to this post is that each person is likely to have a few thoughts hardwired into them from childhood lessons or beliefs. I had the belief that going on dates with multiple girls at the same time was wrong. Immoral, even. Yet I confided in each of them, without specifics, that I would be dating other people, and they were all okay with that. Sometimes going out of your comfort zone is a good thing. Sometimes you need to grow and change your opinion. With these dates, my opinion did changed, and that’s a good thing, I think.


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