So you want to date your best friend? You have a lot in common, you both have similar interests, and your conversations are never-ending. By making the transition, not only will you have a best friend but also a romantic partner. Why shouldn’t you date?
In theory, this is not a bad idea. A part of a healthy relationship is when the two parties have good chemistry and get along well. But before one decides to transition from friends to lovers, you should consider the possibilities for your friendship if the attempt at a romantic relationship comes to an end.
If there is a breakup, how will it affect the friendship? Can the two of you transition back into a friendship as you had before?
Dating your best friend is a gamble you must consider beforehand.
Em**, and I had been friends for three years. Not only friends but the best of friends. We hung out regularly one-on-one, and we’d become familiar and comfortable with each other due to our deep conversations.
One night as we sat a bar, the topic of dating was inevitable. It only made sense for a pair of best friends to move their relationship to the next step. Here in this low-dimmed bar, we held hands and kissed for the first time.
“I knew it!” our friends exclaimed once word broke out since several of them had previously asked if we would ever date.
Things were great for a while, but after some time, this relationship came to an end. During our breakup conversation, we asked each other the famous question, “can we still be friends?”
Sure we could be friends; it wouldn’t be too hard to go back to the way things were.
At the moment, I felt as if going back to being friends was as easy as flipping on a light switch. And it was, at least for the first month, but things quickly began to shift.
We became angry and annoyed each other, so we created distance between us. Group gatherings no longer felt the same when we were both in the same room. And the one-on-one hangouts, don’t even think about it.
Fast forward a few years later, and things hadn’t gotten any better; they’ve gotten worse. We could no longer stand each other and avoided each other as much as possible. We made small talk when we found ourselves in the company of mutual friends, other than that; it was as if we didn’t exist to each other.
After much time passed, I realized a friendship was never going to be possible, but I wanted to make at least an effort to be cordial. I made efforts to intentionally invite Em out to gatherings with new friends of mine. Perhaps this would help mend some of the brokenness between us. She accepted a few invites, and she told me she enjoyed herself.
One of the invites was to attend the Broadway musical Hamilton when it was playing in Chicago. My friends and I had obtained a pair of tickets each. As every one of my friends took either a guest or a date, I considered who I could invite. No doubt, I could have asked several girls to be my date that evening, as the play was very popular, and tickets were highly sought after. I decided to extend an invite to Em, and she agreed.
I could have taken any girl I wanted to see Hamilton with me, but I chose to make an effort on restoring and mending a fractured friendship.
It didn’t help. The friendship wasn’t restored, and to this date, it still hasn’t been restored. It’s been more than a year since I last spoke with Em, I’ve come to terms with the reality that we will forever view each other as people who were once friends.
. . .
Sometimes I wish I’d asked myself this question that night we sat at the bar — what would our friendship look like if we broke up? During that moment I wasn’t thinking about the future. I was only focused on the beautiful girl sitting next to me — the girl who was my then best friend.
We broke up seven years ago, and I’ve asked myself the question several times, what if I’d not asked her out? What if we’d continued only as best friends?
A little while back, she told me that I was once her best friend, and how much she loved me at one point. She said I was a great friend but a bad boyfriend.
I believe this is where the issue lies. As friends, one is free to be who they want to be; to an extent, your life choices will only affect you, and a faithful friend will love you no matter what. However, once a person steps beyond the threshold from friendship to lovers, so do the expectations. Now what you do not only affects and reflects solely on you; it does so on your partner. Where you once were able to indulge in playful banter, your words now carry more weight. As a friend, you could have made mistakes that others could easily brush past, but in a relationship, such errors can be viewed as a red flag. As friends, you can have disagreements, and both can agree to disagree, but in a romantic relationship, inevitable arguments may have you question your desire to remain in the relationship.
People often say they wish to marry their best friend, and I believe that is a beautiful desire. Two people in such a covenant should be best friends. And I desire that for myself one day. But the question is, can best friends date? I believe they absolutely can, and perhaps the relationship may be significant, maybe even lead into a long-lasting marriage.
But what if it doesn’t? Are you willing to gamble your best friend for the experience?
Previously published on medium.com and is republished here under permission.
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