In this day and age of post-feminism and whatnot, it can be hard to figure out healthy, cross-gender friendship. Especially because almost everything attraction-oriented goes unspoken, as already discussed in The Available Sign.
Sometimes, it's easier than others. It's hopefully clear if the guy is married (though sadly this is not always the case) or if there is clearly no attraction on either side. Everything else can potentially be a sticky area...or what I'm calling the Grey Zone. I hate the Grey Zone for the exact same reasons I hate all things where we can't just be clear and upfront with what's going on. There are plenty of single cross-gender friendships that exist in the Grey Zone, and much of the time one person doesn't even know it. Sometimes both people know it, but don't know the other person knows it. And sometimes, both people know it and choose to remain in it because they have issues. I won't bother to waste much time on this dynamic - it is an unhealthy situation that two consenting adults choose to be in, which means only they choose to get out.
The Catch 22 with the Grey Zone is that when dealing with unspoken feelings, we are relying entirely on our own ability to intuitively read a situation -- which no one can do with complete accuracy, and most people can't do at all if their own feelings are involved. And with men and women being as generally clueless as they are about how the other operates (see letter of 2005), sometimes you get one big, fat mess. It's all fun and games until someone gets hurt.
So how to best approach the Grey Zone? As someone who has had more than enough Grey Zone fun for this lifetime, my plea is mostly to the same gender friends out there. If you see a Grey Zone in their life, love your friend enough to ask the awkward question, to suggest they follow more strict boundaries or even initiate a conversation with their possibly attracted friend to get clarity and either start or end something...before someone gets really invested and really hurt. Unfortunately, sometimes hurt is inevitable. But I also believe drama is avoidable.
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