The Brutal Truth About Trying (And Failing) To Date Your Best Friend

They always say date your best friend. You already know you are compatible as friends. A relationship will just make all of those best friend feelings explode into romantic goodness right? Well, the answer is sometimes. Only sometimes. I was disillusioned by the idea that dating my best friend would work. Here is what I learned:

Sometimes he just isn’t that into you, or simply you just aren’t that into him

Loving someone as a best friend and loving them romantically can be quite different. The problem is at first, this love sometimes feels the same. Take time to actually understand your feelings towards one another and openly communicate your thoughts and intentions. If you realize you aren’t into them or they aren’t into you, TALK about it. Moving from best friends to more-than-friends can be a big step, make sure you treat it as such.

Constantly worrying about ruining the friendship can ruin the relationship

A consistent worry across the board is ruining the friendship. While this is a valid concern, it is also an excuse. If you both really want to be together it is worth the risk. It’s only if you don’t truly anticipate a future does this excuse start to dampen the mood. It is important to try to find the balance between protecting the friendship, while also making sure not to use this excuse as a crutch.

Knowing who they have been with can really psych you out

In the past it was always funny to give them shit about hooking up with “X” or cheer them on as they flirted with “Y,” but now that you are romantically involved it is a whole different ball game. You remember story after story of their hook ups with “Z” and how it was good/bad, so naturally it’s easy to worry how they will think of you in comparison. Short answer: don’t compare. Letting your mind worry about the past will only sabotage your happiness in the present. However, this is easier said than done. Knowing who they have been with, especially if it is mutual friends, can be messy. So proceed with caution. If it totally wonks you out, maybe the timing is off and it would be healthier to wait until the dust settles a bit more. The important thing is to focus on what makes YOU happy and what makes YOU comfortable.

Sometimes it is easier to talk about your feelings as best friends than as a couple

As best friends it feels like you can talk about anything. You can have snot dripping from your nose while you cry and you don’t feel the slightest bit of embarrassment. However, at the beginning, it’s easy to feel more reserved when you try to transition to more-than-friends. While you will get that closeness back, transitioning to new territory can temporarily make you forget the camaraderie you once had. It’s important to respect the process here and trust that you will be able to manage this change, while also still maintaining that togetherness. If you don’t start to warm up to each other as more-than-friends, that is OKAY. It is important to stay realistic and recognize if you simply just mesh better as friends.

The thrill of courting each other will fade

Oh, that sweet honeymoon phase. You kiss for the first time and BAM that sexual tension is finally broken. In the moment it feels like that high could last forever. The brutal truth is that it doesn’t. It’s exciting to start something new, especially with someone you already know so well. In this honeymoon phase it feels like you are getting to know them all over again. However, once this fades you should still be left with the same trust and respect you had when you were friends. As a whole, enjoy this new part of your relationship, but don’t set it as your expectation. If you do set it as your expectation and things go south, you will fall far on your ass and boy will it hurt.

You can’t maintain friends with benefits without someone getting hurt, so you rush to define the relationship

The unusual curse of trying to date your best friend is that you can never really be casual about it. Take any friends with benefits-esque movie, someone catches feelings, someone gets hurt, ect. ect. Being long term casual hookup buddies with your best friend has about the same success rate as a Cinderella keeping both of her shoes. Therefore, it is easy to rush defining what you are so no one gets hurt. Instead, don’t be afraid to press the breaks every now and then. Don’t rush to hook up and try to actually better understand what it would be like to date that person. Go on dates or do cute things for each other. It’s not a race to get in bed with each other and instead focus on how you feel emotionally. If the emotional stuff doesn’t seem to settle, then you will be happy you didn’t try to rush.

Don’t force it, it should come naturally

This one seems obvious, but it is really quite important. If that person wants to be with you, they will make the effort. If you want to be with them, you will make the effort. It is as simple as that. It is easy to build up a relationship in your head because you rely on the hope that things will change as you get farther into it. It is especially important when you try dating your best friend. You know how well you clicked as friends, so obviously it will click as easily once you are more than friends right? Be honest with yourself and recognize if they seem checked out or uninterested. Do not make excuses for their indecisiveness and don’t try to force something that maybe isn’t meant to be.

Don’t expect intimacy to magically come together right away

You two are not puzzle pieces, things won’t magically fit together overnight. Much of intimacy is learning from each other and communicating what you like and what you don’t like. As best friends, you know each other well, but will certainly learn a thing or two as you continue to develop your relationship. Be patient with this process and don’t expect fireworks to just happen in one night. By setting unrealistic expectations for your sex life, you in turn don’t give yourself a fair chance to learn about your best friend.

Communication is key, but make sure you don’t just hear what you want to hear

Right so communication is key, we all know that. BUT, it is also important to not just hear what you want to hear. They say that they “like you, but…” Listen to what they say after the “but!” While it is easier to hear the positive and rely on hope to solve your problems, you need to hear each other out all the way through. Communicate, communicate, communicate, but also listen to what they are truly saying, even if it is not what you want to hear.

Don’t put each other on a pedestal

It’s your best friend, right? You have been there for each other so many times. It’s easy to believe that in a relationship they will be the best boyfriend/girlfriend you have EVER had. So if expectation doesn’t match reality it ends up feeling like a huge disappointment. The biggest piece of advice is just to base your thoughts on their actions and not on your preconceived expectations. Learn about them as you go, instead of imagining them as perfect from the start.

Know your self worth

Yes they are your best friend, but YOU are also your own best friend too! If they aren’t treating you right, it doesn’t matter that they are your best friend. Being your best friend doesn’t excuse them from being an asshole. Love yourself and know yourself enough to confidently demand respect at all times. They don’t get a hall pass for being your best friend, rude is rude and you should always prioritize your happiness and self worth.

Remember that at the end of the day, this person is STILL your best friend

Without placing expectations on each other, remember that your friendship comes first. You are best friends and hurting them will only really end up hurting you too. Communicate if things aren’t working, don’t merely toss them aside and ignore them. Treat each other how you would want to be treated and don’t play games with each other. Some of the best relationships can be the product of dating and falling in love with your best friend. However, falling for your best friend is way more complicated than it seems. In all, don’t lose sight of your friendship, prioritize your own self worth, and recognize when it may be time to let go. TC mark

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