Requiting the unrequited

Few things are capable of producing more sublime joy or more exquisite grief than the prospect of taking friendship to the next level.

It’s a familiar scenario: Two people have been friends for years, get along amazingly, and genuinely enjoy each other’s company. And then one member of the dynamic duo starts to feel the soul-rending twinge of Cupid’s arrow.

At this point, the relationship’s status quo teeters on the edge of a precipice: On one side, the same comfortable, but ultimately predictable friendship languishes; on the other, a misty, uncharted realm harbours unseen perils and pleasures.

For a lot of people, this tenuous point is as far as they reach. Nerves, cowardice, or a general unwillingness to plunge into that great unknown has resulted in many a potentially beautiful romance withering on the vine.

But for those brave few who do decide to jump, two possibilities await: Either your friend reciprocates your affections, and the magic of transitioning from friends to lovers begins; or the same friend invokes the “let’s stay friends” clause.

The second outcome is obviously less than ideal, and the fear of ruining a perfectly good friendship is a rational one.

But as someone who’s succeeded in taking a dear friendship to the next level (and maintaining it, in spite of all my shenanigans), I’m a big exponent of jumping in head first.

That’s not to say you should jump in without a fairly good inkling that your feelings might be mirrored in your friend.

Once you identify the pangs of longing, it helps to soothe them with a generous dose of realism: Are you in your friend’s league, physically speaking? Are you certain they don’t have eyes for someone else (hint: usually they’ll tell you)? Can you conceivably picture the both of you having sex?

If you, after a good measure of self-scrutiny, can answer the preceding questions with a resounding “you betcha,” making a play for your friend probably the next step. As I see it, if you’ve reached this stage, you have more to lose by not telling your friend how you feel. After all, time heals all awkwardnesses.

It’s better to put it all out there and risk a few months of weirdness if (yikes) your intuition was clouded by wishful thinking. The rewards of success are totally worth it.

If, when you confess your aching love to your pal, they immediately throw themselves upon you and all the pent-up sexual tension between you both outs itself in a supernova of flailing limbs (or, you know, a lesser degree of happy realization), there are a few things to prepare yourself for.

First, there’s going to be a huge rush of emotion associated with suddenly getting everything you wanted (especially if your infatuation has been building over a period of months or longer).

While this cloudburst of emotion signifies a wonderful thing, it’ll be an unruly beast, potentially running the gamut from feelings of disbelief and self-doubt to random bouts of crying.

This emotional spike will gradually subside, easing into the tug-of-war of feelings that makes up any loving relationship.

The second thing to prepare for is how truly awkward your first few times in the sack will be. Oh yes, they’ll be awkward.

While one of the greatest things about turning a friend into a lover is that you’ve already leapt all the getting-to-know-you hurdles, getting to know your friend sexually might be all new.

There’s a lot of pressure during the first few times you have sex, pressure not to do it badly in order to justify the jump from friends to lovers.

If it doesn’t go well the first few times, just chill: Keep in mind sex with any partner at all generally doesn’t get good until you figure out all of your partner’s sexual idiosyncrasies. It’s easy to lose sight of this fact, given what you both have at stake.

A final thought on the subject – I’m not a big fan of writing an opt-out “let’s pull the plug if things don’t work” clause into the burgeoning relationship.

If you’ve gotten as far as you have, you might as well have a bit of faith that you guys will work out. You don’t want to set yourselves up to fail. If things do fall apart, you can be certain that, in time, you’ll rediscover what bonded you as friends in the first place.