How to not ask your best friend out

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I asked my best friend out while we stood on a dock overlooking Lake Washington on a beautiful sunny day in Seattle. I had planned this moment for a couple of weeks and finally sprung the question on him at the last second (before I lost my nerve). I had thought it might be “our dock” but instead, it’s just the dock where I displayed tremendous courage and felt immensely stupid for it. So, it’s my dock in a way.

And he said no. But first, I had to clarify what I meant because, apparently, he had not even thought of this and seemed shocked to hear me even asking. Or if he had, he had made his decision a long time ago. Ironically, many months later (after we had both recovered) he told me he had always found curly brown hair attractive and I laughed at this, said “Not always!” to which he sputtered some lame defense (like, “oh, no it has to be darker.” but in his defense, I had red curly hair when I met him).

So, if you know that your best (guy) friend (who, by the way, is not gay) is not that into you but you think you can change his mind and make him love you, don’t ask him out – no matter how ridiculously perfect the setting or how much you love the guy.

In my case, it turns out my best guy friend did love me – just not in the way I had hoped for. I’ve come to realize that it’s a better thing – to have that – than to get what I wanted.

Created: Nov 22, 2010

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