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Dating Diaries: I Came, I Casually Dated, I Didn’t Conquer

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It turns out my strategy for emotionally safe casual dating does not work. Try to look surprised.

I was thinking about how I never text or call the guy, or make any of the plans or really ever pay for anything, and I just felt like a jerk. If I were him, I would probably feel pretty bad and full of doubt. Even though he announced that he didn’t want anything serious right before our first kiss, which is basically just giving himself permission to treat me however he wants because I’ve been given fair warning, that doesn’t excuse me from doing the same.

In a way, it’s really easy to “play it cool.” You just do absolutely nothing. But since it isn’t natural for me, it’s a lot of hard work and I don’t feel like I’m being true to myself. I should treat the person I’m dating like I want to be treated, even if that is it’s own reward. And despite having me sign on the dotted line to guarantee we’d never be BF and GF, this guy isn’t treating me badly at all. I don’t think it’s inherently wrong for people to not want commitment, and it’s not like they can be expected to be celibate, but when you figure out how to date that way without hurting someone please let me know.

My first act as a reformed casual dater was to try to cheer him up after he told me he’d had a bad week at work. I plotted out an evening where I’d take him to my favorite BYOB Vietnamese restaurant then to this nearby dive bar with Jello shots and Everclear soaked pineapple. Jello shots are my favorite cure to a bad week. I even baked him a chocolate cake because I had said that I would after he insisted on paying for my towing fee after the first time we hung out (long, kind of romantic story).

Then I accidentally got into a feminist rant about something someone said to me on Facebook (Um, Annoying Things Millennial Girls Do on Dates for $500, Alex).

As the night drew near, I started having doubts about the cake, though. I love to bake for people, and I wanted to be good to him, but maybe it’d be too nice. Then, he got stuck at work and didn’t pick me up until 9pm, which was totally fine except that the restaurant was closed and my plan had to be scrapped. The first thing he told me when I got into the car was that he decided to stop eating gluten. I did not mention the cake waiting in my kitchen.

I should have had a plan B, but I didn’t, so we drove around the neighborhood for a while trying to think of somewhere to eat. To pass the time, for some reason he told me a story about a bartender we both know who used to have an aggressive crush on him. Okay. Why would he say that to me? We ended up in a restaurant across town and our conversation was stalled and awkward. I accidentally got into a feminist rant about something someone said to me on Facebook (Um, Annoying Things Millennial Girls Do on Dates for $500, Alex) and then I just felt tired.

Related: Be a Better Dater: Why Having a Plan is So, So Important

Back in the car, we went ahead and drove to the Jello shot bar. Things improved over a friendly game of shuffleboard but so far there had been no touching. Usually he grabs my hip or touches my arm or even kisses me before that point in a date. Naturally, I started wondering if he was going to break up with me the same day I had baked him a cake he couldn’t eat. He didn’t, and we went home together, but the whole time I felt like I had to try hard to engage him. So much for my new Golden Rule of dating. I still felt scared all the time.

Obviously, the reason the date went poorly wasn’t because I finally decided to pull my weight. I don’t know why it was so depressing. But I know that two people going through the motions of dating despite an imminent breakup is probably never going to work for me. I’ve broken at least 3 of my New Year dating resolutions with this guy alone.

Related: 10 Bad Habits Girls Have on First Dates

The reality is that I’m just not a casual dating kind of girl. It’s not that I need an engagement offer on the table before the month is up, but I do need the opportunity for things to grow. Of course things should be  low commitment in the beginning, but heartbreak is way too painful for me to risk it with someone who has no intention of seeing things through.

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