Her Story: What I Learned From Trying to Date My Best Friend

It’s happened to almost everyone. I’m sure a lot of people can say they have fallen for at least one of their friends in their life. For me, this happens almost too often and almost never works out. But, there was one friend of mine, “Cal,” that things had actually worked out for me -- for a bit.

Cal and I hadn’t always been friends, but after meeting each other in the school play my junior year, we clicked instantly and became close. There had never been any feelings to begin with, because both of us were involved with other people at the time. Eventually both of those other people were out of our lives, but still we were just friends and nothing had ever been thought differently.

Then, senior year, there was a different feeling in the air. I was involved with someone else, but things had fallen apart with him one night and I was upset. So of course, I texted Cal. We talked for hours that night about serious topics, something that had never been a thing for us because we were always joking around. I was still hung up on the other guy, but at that moment, things didn’t seem as horrible as they did before I talked to Cal. We then started texting all the time, and eventually I began sneaking him out of his house…

It was a Friday night. I had gotten home late from a football game and I was extremely hungry. Because I’m like every other person in the world, I tweeted about it. Cal had answered me, saying I should pick him up and we could go out to eat somewhere. Of course, I tried and it failed. We then planned to properly sneak out the next night, and we did. It became our thing without either of us actually realizing it was a thing.

A few weeks later, Cal and I were having a conversation about movies, except this conversation had seemed flirtier than previous ones. At one point he had told me he wanted to see a movie, and then proceeded to say that he and I should go to one. Because Cal and I were best friends, I thought nothing of it and told him I would love to see a movie with him. It wasn’t until later he told me that he had been asking me out on a date, which caused me to freak out. I had never actually been on a date before (the other boys I had been involved with had never properly taken me out anywhere), and I didn’t know what to do. When the date finally came along though, we were fine and laughed at each other all day.

We went on a few more dates, and Cal had defined our relationship as that we were dating, without the titles of boyfriend and girlfriend. I got plenty of texts from Cal saying how beautiful I was, how smart I was, and many other things that boys had never told me before. We were planning how we were going to spend Christmas break and everything was great. I wondered why if this was how it was to date your best friend, why weren’t more people doing it?

My question was answered a week before Christmas when I knew something wasn’t right. Cal began cancelling dates and not being able to hang out as much. I didn’t push him about it, not wanting to be the kind of girl that obsesses over the smallest thing. Instead, I expressed my concern to a mutual friend, not actually expecting her to run to Cal and confront him. It led to him telling her he wasn’t sure if he actually liked me beyond friendship, and everything came crashing down.

 I was starting to ponder how much of a waste the last few months had been, and there was nothing I could do about it. I waited for the inevitable text I was going to receive that night from Cal, saying exactly what I had heard earlier and making the words a reality. I read texts upon texts of him apologizing and saying that he had known for weeks, but was just trying to slowly cut me off instead of just telling me the truth. He still wanted us to be friends, but I was heartbroken. My time with him was was one of my first experiences of actually dating someone. I even met his parents! I just didn’t understand how someone who was supposed to be my best friend could hurt me. 

I went into the relationship very naïve and unexperienced, but I also learned from it. I learned that you have to watch who you trust and you who let into your heart. Just because someone’s your best friend doesn’t mean they’ll never hurt you. The whole experience has altered how I am around boys and with relationships. Now, I have stronger walls and am more cautious in relationships, because all I can think about is what if they’re just joking around and unsure about everything, just like Cal.

Now, the whole experience won’t deter me from dating any other friends I have in the future. In fact, I eventually became friends with Cal again after the whole experience, although it didn’t last long. It wasn’t the same as it used to be. I sometimes find myself lingering on what was, but I don’t regret a moment of what happened. It taught me something important, something no book, TV show, or adult could teach me properly. I have so much left to experience at college, and all Cal reminds me of is high school. I need to stop lingering on the idea of him and think of the future. High school was something I was done with the moment I graduated, and have no desire to ever return anytime soon.

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