August 31^st, 2007 was the first night I ever spent the night at my best friend Leslie’s house. Although this date has gone down in history as just that, celebrated annually as our friendship-a-versary, there was something else about this day that changed my life forever: it was the first night I met her brother.

Standing awkwardly outside of a local laundromat, I watched as this guy pulled into the parking lot to meet us. He was extremely tall, towering over me at six feet, two inches, and had that teenage bad-boy look to him. I was intimidated. I expected him to be as obnoxious and annoying as the friend he brought with him, who was making mean jokes and play-fighting with Leslie. However, he didn’t speak. He stood a distance away from us, his eyes shyly focused on his feet. Leslie dragged me inside, wanting to get away from the boys, and we sat on a bench and talked until her brother stood in front of me and put out his hand. He was holding a little teddy bear keychain that he had got from one of those candy dispensers that shell out prizes instead. He mumbled “here,” placed it in my hand, and walked off, leaving me to wonder what had just transpired between us. The conclusion I had come up with was nothing compared to the future that was in store for either of us.

That was the beginning. That was a lifetime ago. When I think about it now, a mixture of sadness and nostalgia drown my being. What I would give to go back and see if I could have avoided such a mess. To see if it would have made much of a difference if time allowed me a do-over. After our introduction, the more I would spend the night, the more he would joke about us being together. I ignored it, they were only jokes. But jokes turned to more jokes, more jokes turned to feelings, and the rest is history. There was only one problem. Apart from the blood ties that make you love your family, siblings have a tendency to despise one another. In this case, the rivalry was the equivalent of a third World War.

They would fight and of course, your friend expects you to have their back. But so does your boyfriend. Whosever side you took, you would still have to face the wrath of the other person. It was a lose-lose no matter what I did. That was one issue. Then I had to consider splitting time spent between the two. This would cause fights as well because your best friend feels like you are leaving them for the one person they can’t stand and your boyfriend thinks that his sister is taking you away from him. Basically, dating your best friend’s brother puts you right at the center of pre-existing and self-created family feuds.

Another thing to consider: you want to tell your best friend everything, right? Well, hearing about your romance with their brother is NOT something that perks up their ears. If anything, it would leave them screaming in agony, begging for the gory details to worm their way out of their brain. You want to tell your boyfriend everything? Well, that’s out of the question, too. Each has secrets they want you to keep from the other. If you didn’t know something was meant to be a secret and accidentally spill, both will get mad and you’ll be in a never-ending battle for the trust and affection of both your best friend and your boyfriend.

And let’s not forget what happens if your relationship ends, whether it be a nasty break-up or a mutual agreement. You will still have to see that person anytime you wish to see your best friend and nothing good can come of this. Either old feelings will resurface that create complications, or you’ll be so afraid to see that person that it’ll affect the time you spend with your best friend.

In the end, the wear and tear of the extensive measures you take to ensure both are happy with you and happy with each other will begin to take its toll. You will be exhausted to the point where even death doesn’t seem to be enough rest and you will begin to shut down. Because in the end, they are family and family doesn’t let outsiders get in-between them. Because in the end, it’s either you choosing one, walking away from both, or both of them walking away from you. And how can you afford to lose the two people you care about the most?

So, my advice is don’t. Don’t fall for your best friend’s brother. Don’t make either one of them feel less important than the other. Don’t cause a lifetime of drama for either of you. Don’t take sides. Don’t choose. Don’t feel like you have to walk away from some of the most important people in your life. All of this can be avoided. If you ever meet your best friend’s sibling for the first time and think, “this person is actually really attractive and charming,” just leave it as a passing thought in your head and forget that it ever happened. Trust me: it will be worth it.