Bound By Friendship

Dear Mistress,

I’m a single woman, 38 years old. I’ve known my best friend — let’s call him “John” — for more than 18 years. I think I fell in love with John’s smile the moment I met him all those years ago. We were both so young and carefree. It seemed like something would happen between us, but it never quite got off the ground. After a couple years, I met another man and got married. John became distant. When I got a divorce four years later, John came back into my life. Again, nothing happened. When he got a girlfriend, I couldn’t bear to see him with another woman and kept my distance for three years until they broke up.

Now, here we are, both single and inseparable again. We both date, but we don’t talk about it. I find myself comparing every man I date to him, which seems unfair to the guys I date — and yet I cannot figure out how to tell my best friend that I would gladly spend the rest of my life with him. A couple close friends are encouraging me (hounding me is more like it) to finally tell John my feelings, but I just can’t. He hasn’t said anything all these years, so why should I expect that he’ll return my feelings?

Signed,
Bound By Friendship

Dear Bound,

I liken your situation to playing the stock market. Do you want to make a safe investment to gain a modest and reliable return — or do you want to make a more risky move and possibly cash in big? Are you willing to put your friendship on the line to possibly gain the biggest love of your life?

You don’t want to lose John’s friendship, but let’s face it: It’s not a true friendship if you’re hiding deeper feelings from him. Though you might have to move out of your comfort zone, consider sharing your feelings with John. Unrequited love rarely ends well, and you don’t want your secret feelings to slowly erode your relationship.

Don’t hide behind the excuse that he hasn’t said anything all these years — you haven’t said anything, either. You have both avoided one another when lovers and spouses were in the picture, and this indicates a deeper level of intimacy. Don’t remain in a state of suspended animation. Take a chance and tell him how you feel. Sometimes you have to climb a scary tree to find life’s sweetest fruits.

Cherry pickin’,
mm