Tag Archives: Andrew

File No. 1: Wows and Woes of the Flirtatious Friendship

9 Nov

So I have this friend who is a boy.

Our friendship is brilliant–substantial and interesting, casual and intimate. We’ve never kissed,  never have been any more intimate than a hug, an occasional hand-holding and an inadvertent snuggle in his bed once, when I was having a really shit day. Our friendship means the world to me, it always has, but there was a while when it was touch-and-go. Not because we had fallen out, but because we had both secretly fallen for each other.

To use a dated analogy, he was Luke to my Lorelai. He was always there, always coming around to help me out with things. We’d even go on casual dates and it was clear that we were both harboring feelings for one another, although those words never escaped either of our lips. We flirted, mostly, and confessed that we loved one another without qualifying if we meant “in that way” or not. But, there were things holding us back. He’s celibate. I’m not. He wants to wait until he’s married and at the time when he and I were at the apex of flirtship, we were both doing undergraduate degrees. Marriage was nowhere in the cards. Still, the flirting persisted, to this day, although I’m in a stable, live-in relationship and completely content, we maintain an element of our flirtship. Of course, it’s not as heavy as it once was, but it’s still there.

These types of situations, for me, are the worst. You’ve found someone whom you completely click with. Whom you love being around, and who makes you a better person. There are the wows.

The woes? That age-old fear that initiating something more than a friendship will ruin what you have. There’s nothing worse than losing a friend to the pincers of failed love. Of course, there’s nothing to say that the two of you won’t have a happy relationship. There’s nothing to say you will, either.

It’s the worst type of catch twenty-two there is. What do you risk? If anything?

I’m not going to lie, our friendship is different. The dynamics have changed, as they should have. This guy, Andrew, and I have been friends since I was a freshmen in college. That’s five years ago. Two years into our friendship, it became a flirtship and about three years in, we were on the brink of needing to have “The Talk”. Except, I moved out of the country for a spell and during my stint away fell in love with my current partner. When I came back,  mine and Andrew’s flirtship was nearly dehydrated. He was so cautious about breaching my current love. He put up walls and was difficult and I knew and all my girlfriends knew why.

Things maybe would have been different if either of us had gotten the kahunas to say, “I love you, you idiot” and see what developed. But, for whatever reason, we didn’t. Are we better off? I’m not sure. I’m content, I’m ecstatic about my love life and I couldn’t imagine loving anyone else and I would never trade Michael for anyone. Still, one of the biggest woes is the nagging thought I have from time to time: What would have happened if … ?