Dating your best friend. Pitfalls and high points

Many people through time have dated their best friends. For some it happens organically where they go fluidly from the friend zone to the significant other zone. For some it’s more of a deliberate move where they look around, see no worthy mates in a sea of potential mates, finally spot their best friend and realize that they’re better than almost all significant others they’ve had in the past.

No relationship is perfect. Expecting perfection in any relationship is like expecting your underwear size to remain the same your entire life. It doesn’t remain the same. Even when it may start at a perfect spot. It doesn’t remain the same. Over time there are things that even the best of friendship-turned-love relationships go through that change the way they look and function.

Overall it’s a nice and comfortable thought to end up with someone whom you have known so closely and platonically. Someone whose shortcomings and strengths are so known to you. Someone you have seen in other relationships while you were their friend.

My suspicion is that may be some spontaneity might be missing from such relationships. I mean if you’re someone who likes spontaneity then you might be perturbed by that. If you are just another low-key relationship adventurer then the lack of spontaneity may even be welcome by you.

Also, there could be a lot of comparison drawn by you between this person’s relationship with you and with other people in the past. You might sense that your boyfriend isn’t as romantic with you as he was with that other girl he was dating. You’ve just been privy to a lot of relationships that he has had before. It’s hard for you to not compare his passion for his relationship with you with some of the past, steamier ones that he has had. It’s tough to know so much about someone’s history and not feel like a part of it. Even if your part was usually that of the shoulder to cry on after breakups, the advisor, the moral support.

Best friends becoming lovers is also fraught with another complication. People like to claim that they always saw the chemistry. That they always predicted this would happen. While you’re trying to create something by treading into the love zone carefully there are people who are already discussing what your kids would look like. In a world of failed relationships, people find two friends dating weird but don’t say it. They try to make peace with the concept by subtly and openly hinting that they always suspected something was going on. It’s exhausting to correct these people. It can easily wear on a relationship too.

Another pitfall that I personally see with dating a best friend is the fact that there are no surprises. I’m thankful that there aren’t any bad surprises but even the good ones aren’t there. When you’ve known someone for many years in the capacity of a best friend there is little that you don’t know about them. True that some women have said that their best friend was a completely different person when he became a boyfriend but how many people become “completely different”? I feel like it’s a way to make ourselves believe that we are dating someone different from our best friend. Like we have a real boyfriend. It’s a mind thing. It’s hard to “unfriend zone” our former BFF who is now our BF. Do I perceive it as sad? Sometimes. Sometimes when I see people reveling in knowing their best friend in a modified capacity I feel like there’s so much potential for these matches.

But there must be good sides to it also, right? I mean are these relationships only fraught with desperation, lifelong struggles with navigation as romantic relationships, and the constant figuring out of how to take it to the next level?

I guess one good side is the amount of camaraderie that these relationships share. How easily such people can laugh with each other and how little they have to guess about their significant other’s favorite restaurant.

Another good side could be the friends’ circle that would practically remain the same. No one has to know new people and pretend to like them. It’s all already set. Everyone is really friends with each other. Yes people have started acting a little awkward around the two of you but who cares? They’ll come around.

I think the one pitfall of this relationship isn’t while it’s thriving and jiving. It’s when it ends unfortunately. If this relationship ends you don’t just lose a SO, you really lose your best friend. That’s a huge loss. That’s why it’s generally not recommended. That’s why so many people stay away from it. That’s why all the chemistry, all the convenience, all the camaraderie in the world hasn’t been enough to make a favorable argument for this concept in my head.


  1. May I share in a couple of sentences what I think is the key to success for sustaining any relationship. One should just focus on one’s obligations without ever expecting anything in return, and of course this should be done in a loving manner. In one word, act like a true human and enjoy the beauty of life.

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  2. Must say that you have analyzed all aspects of this relationship beautifully. The way you write makes one believe as if you have gone through every aspect of that. That is wonderful. I have noticed your examples are usually very funny, but convey the point in a compelling manner. I am referring to “Expecting perfection in any relationship is like expecting your underwear size to remain the same your entire life”.

    Liked by 1 person

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