During a short-lived single period my freshman year, I committed the cardinal sin of friendship—I tried to sleep with one of my best friends.
Ray and I knew each other for over two years, and from the second we met, we had a form of solidified bond that seemed infinite—a bond only found in a best friendship. He consoled me through break-ups, told me tales of his sexual escapades, and even let me crash in his bed on nights when I was disastrously drunk. Throughout the years there were brief moments of flirtation between us, but nothing ever came of it.
Until Pride my freshman year, when I was out with Ray and his roommate—who I actually ended up dating. It was the sort of Four Loko fueled evening that pretty well encapsulates the entirety of my first semester at Rollins. As we prepared to leave the club, I decided to kiss Ray. We belligerently tried to hook up, which eventually ended with me regretfully telling him that I loved him, and the rest of the night turned into an awkward affair of emotional and physical interplay.
It didn’t end well. Not only did we end up not having sex, but also our friendship was now contaminated with my emotional admittance. I started dating Ray’s roommate a month later, and eventually the culmination of these events placed a wedge between us—our once solidified bond began to crumble. Three months later, our friendship ended with a hostile fight—the fallout of which not only destroyed our friendship, but also his friendship with his roommate, my boyfriend.
The moral of this anecdote is pretty clear to me: under no circumstance should you attempt to sleep with your best friend. But then again, I have known people who have slept with their best friend, and it has ended in a powerful romance. A past co-worker, for example, ended up marrying her best friend of almost twenty years. Navigating between friend and lover is like walking an emotional tightrope, but there is the possibility for success worth pursuing. In an attempt for clarity, here are a few tips for walking the wire.
Sobriety is key: In hindsight, I should have never advanced Ray sexually while I was under the influence of alcohol. We all know how alcohol impairs cognitive function; in this case, alcohol operates as a lubricant on the friend/lover tightrope. I’m not saying you shouldn’t drink with your best friend—just be careful not to use alcohol as the catalyst for sex with him or her.
Creating a contract: The top reason people avoid pursuing sex with a friend is fear of losing the friendship all together. In the case of Ray and I, the friendship was over the second I began to pursue him sexually. In order to mitigate this fear, it is necessary that a metaphorical contract be crafted between both parties.
The people I know who have successfully converted their best friend to a lover are those who create clear boundaries. Communicating your feelings for one another and seeking mutual agreement through this contract crafting is necessary for ensuring that no one gets hurt. Of course, feelings can change after sex is introduced in a formerly platonic relationship. You will need to continue to clearly communicate with one another throughout the entirety of your affair—in theory this should be easy, since friendship is initially formed through clear communication.
Do not involve outside parties: Deciding to sleep with a best friend is one thing. Deciding to share the news of your newfound relationship with others is a completely different thing. Going public with a relationship is never easy, especially when it could affect your entire social group’s stability.
Friends who become privy to your transitioning relationship generally react in a polarized manner: they either hate or love the idea. When it comes to shifting social structures, everyone has an opinion on the matter because it affects them too. When best-friend-gone-lover relationships fail, they have the tendency to destroy not only the relationship between you and your best friend, but also your friends’ relationships with that person.
So prior to going public, consider the ramifications and be prepared to accept responsibility for the possible changes in your social sphere by diving into a relationship with a friend.
I wish there was a clear answer to the question, “Should you pursue a sexual relationship with your best friend?” Unfortunately, only you can answer that question clearly of your own pursuit. In the case of my relationship with Ray, I am filled with regret for destroying a friendship that once seemed so strong. We ended on a note of hostility, and to make things worse, he unexpectedly passed away over a year ago. I never had the chance to apologize for destroying our friendship, but our story serves as warning for those of you deciding to walk the wire.
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