Differences: Casual Hookup With a Stranger or Your Best Friend

casual sex with friendThe opinion on whether to engage in casual hookups varies amongst different people. Some think it is a waste of time; others feel it fits their lifestyle very well. I, on the other hand, have always enjoyed casual hookups. I’ve never been shy about meeting a stranger and hopefully if I like them, I will go the distance, but only for that one night. Sometimes I may have several hookups with the same stranger over time. It is important to know that emotions should never be involved and that it is only at that particular time. Some of my friends worry that I am becoming a bit of a slut and that I should spend that time looking for a meaningful relationship. This assumption does not worry me at all. Casual hookups simply work best for me as I never have time to date. My work involves a lot of unscheduled traveling and hotel boarding. There’s just no room for me to be a loyal girlfriend to any one boyfriend. But when it comes to friends, I have plenty of friends. I am loyal to my friends. Especially my best friend, Kevin.


Kevin and I met in college almost 16 years ago. I was easily drawn to him for his humor and humility. He came from a well to do family and I, on the other hand, was barely struggling to get by. We were never romantically inclined to one another and would always share opinions on the people we were dating. Throughout my career, we have always found ways of keeping in touch even when we can’t physically see each other for long periods of time. Whenever we get a chance to meet, it’s always a fun time. Kevin is the one true friend that has never judged me for my casual dating style. If I’m not choosing my casual date online, Kevin almost always helps me pick out the most suitable guy at the counter. We are each other’s best friend. One night, as we always do whenever I am in town, we met up for some drinks to catch up. The night went on as usual. A few shots here, some pool playing and long talks. He tried to show me a couple of guys I would like, and I picked out a few females he would like, but somehow that night, none of us scored. One thing led to another, and we ended up waking up in my bed! I must say, it was one of the weirdest casual hookups I’ve ever been engaged in. This was my best friend. We, however, decided it was just that one time and vowed to continue keeping in touch, as friends, just like we always have. That didn’t go as planned.


The calling and texting dwindled, and whenever I was in town, I was too afraid to call him up. The difference is whenever I hook up with a stranger, and I want to link up with them again, I have no problem looking them up anytime I am in their vicinity. I think it boils down to the fact that with a man I barely know, I am not hoping for a relationship, it’s simply casual. No strings attached. The makeup of casual hookups depends on finding the person with the exact understanding of why we are both there, and no one feels used or cheap. There are times when you find that one person who will want to go further than just the casual hookup and addresses the desire to have a relationship. For me, it is easy to stay unattached because my schedule just doesn’t allow it. I will usually explain this to the other party, be as honest as I can about my situation and quickly end it.


casual hookup with best friendWith Kevin, I ended up being the one who wanted more than that casual thing. I couldn’t get myself to see any other guy. I found myself thinking about him constantly, and not just as a friend. I gathered up the courage to call him one day when I was in town so we could meet. He agreed. We met up at our favorite pub, but this time, I got dressed up … Something I usually never do when am meeting Kevin. I was nervous and to say the least; the conversation was awkward. After a few shots, we put all that behind us and started having fun like we always did. Strangely, he never pointed to a guy he thought would suit me for the night. That night ended up with us waking up in his house in the morning. We did it again! It is at this point that I usually have the am not able to commit’ discussion that I always have with all my other casual hookups. But I couldn’t with Kevin. I left without saying a word. I wanted this to go on. So again we hooked up all that week until I had to travel again. Kevin offered to take me to the airport. As I was ready to get in, he looked at me and said, “You know this was just casual, right?” I cannot tell you how many times I’ve used that same line to strangers before. Hearing it from my best friend was crushing. I immediately realized I had become attached to him. But he, on the other hand, was only having a good time. I decided I will not let that sway me. I know Kevin very well. He is going to come around. I will continue with the hookups and pretend I have no feelings for him. So after a treacherous three weeks away, I came back to town and asked if we could meet. He was more than excited to meet up as, like he said, had someone he wanted to introduce me to. It was a girl, a very beautiful one I might add. He has been dating her and wanted my opinion on her.


Here’s the thing, casual hookups are a great way to get what you need for that time. As long as both parties are well aware that no emotions are involved, it can turn out great. With strangers, it is so much easier because you have no prior feelings towards the person and might take time to get to know them. When it is your best friend, the casual hookup may come as a surprise, but it may take a turn for the worse because this is someone you already love. And when the hookup is great, the emotions may overflow even without realizing it for either one of you. Chances of your friendship ending are high if someone is hurt in the process. Kevin did eventually marry the girl; I still go on as I am with no regrets and our friendship is even stronger.

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