Should I Date My Best Friend?

One of the biggest challenges that any relationship can face is transition. While all relationships change with time, it’s rare that one undergoes a complete change in context and tone. Here we address Andy’s concerns about dating his best friend.

Andy from Boston, MA writes:
“Recently I’ve been experiencing a change in my feelings toward my best friend, Whitney. We’ve been best friends for years now; we met in high school, attended college together, and now we’ve graduated and stayed in the same city. I’m completely comfortable with our relationship as it is—it’s perfect. But I find myself feeling romantically toward her and I’m not sure how to express this or if I even should. I know it sounds stereotypical, but will I ruin our perfect friendship if I try to date my best friend?”

“Hi, Andy. There’s no simple yes or no answer to a question like this, since every friendship is different and built on different things. Whether you should date your best friend or not is going to come down to how you both handle change, whether this is an unspoken boundary or not, how you both experience attraction, and more.

For some people, dating a best friend is the best decision in the world. Without true friendship at its core, no romantic relationship will survive for very long. Friendship denotes the mutual respect, love, and trust which is central to any other relationship. That means dating your best friend could, potentially, result in an ideal romantic relationship as well.

For other people, dating a best friend is the worst decision possible. Sometimes you end up mistakenly crossing unspoken boundaries which have always been present—and foundational—in a friendship. You may not know whether those boundaries even exist, but your best friend may feel they do. If you don’t get any obvious vibes from her that she’s romantically inclined toward you, you may want to proceed cautiously so as not to make her uncomfortable. Does that mean you shouldn’t try? Not necessarily; the only way to know is to ask. Keep in mind that a lot of people feel attraction immediately or not at all—while other people feel no attraction in the beginning and only form that kind of bond later on. This can result in confusion in situations like these.

Another reason dating a best friend might not work is that in romantic relationships people often pay attention to different things and have different needs than they do in their platonic friendships. You and your best friend may be perfectly compatible platonically but have completely different expectations from a romantic partner. It isn’t uncommon for two people who get along great to suddenly drive each other crazy if they start dating.

On the other hand, you may find your romantic ideals match up just as your platonic ideals do, in which case it could be a great situation. Hopefully this gives you a starting point and some things to think about before you decide whether to approach your best friend about the idea of dating.

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2 Comments

  1. damir says:

    Hey,
    Well hard one to answer. I would say no but my love of my life was my best friend.
    It is my best relationship so far and I don’t see it ending any time in future.
    Hard one to answer.
    Cheers,

  2. Jon says:

    I found myself in the same situation. I dated a girl my freshman year of high school who eventually became my best friend. We ended up going to prom together as friends. We began hanging out daily once we went to college, once again my feelings for her began to grow. I struggled for a while as to whether or not I should attempt to date her. After a while I decided to tell her how I felt and talk to her. We talked and decided to wait it out and see how everything works out. About five months later we began dating. To make a long story short we are now engaged and I am happier than I ever could have been. The advise I would like to give is talk to her, let her know how you feel if you have the friendship you feel you have then she will understand. Yes it will be a challenge, honesty is the best thing in a friendship. Best of luck hope this helps. I know what the situation is like.

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