Whoops -- I did it with my best friend's boyfriend

She went away for the summer and one thing led to another.

By Cary Tennis
August 15, 2005 8:15PM (UTC)
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Dear Cary,

I am in a panic tonight.

About a month and a half ago I basically slept with (in the Clinton sense) my good friend's boyfriend. My friend and I are law students. We'll call her Jane. Jane is out of town for the summer and she left her boyfriend (whom we'll call Sam) here after begging him to come live with her. I adore Sam, but we both knew it was best not to fool around anymore. So, we've done a good job of just remaining friends. I've done my best to deal with the guilt and moral implications and I've decided for the good of everyone I wasn't going to tell Jane what happened. I didn't want to be the one to break up a five-year relationship.


My new problem is this: I told a friend of mine, Ben, what happened during a drunken conversation the night after it all happened. He promised not to tell a soul. Today he told (kind of by accident). And he told a mutual friend of ours. Carolyn is young. She is 22 while I am 29. She called me tonight and told me what she knew. She then proceeded to tell me that she thought I did a horrible thing, that I should tell Jane and that she didn't think she could trust me now. I am scared that she is also going to tell Jane.

I don't want to defend my actions because I know they were wrong, but I want to tell her to stay out of my business. There is no good that could come of her interfering. I feel in danger of losing a bunch of friends here and I'm pissed off, but I feel selfish for being pissed off. I felt like Carolyn was my friend and that she could deal with a revelation that I wasn't perfect. But she couldn't, and I just want to tell her that I think she is too self-righteous and moralizing and someday when she grows up a bit, she might understand. But I don't want to lose her as a friend and I don't want her to tell Jane. So, do I just keep quiet? Is it best to come clean to everyone even though it might really mess with some lives? Is it any of her business? I feel like my world (and maybe that of a few others) is about to come crashing down.

Usually a Good Girl


Dear Usually a Good Girl,

I remember getting your first e-mail a few months back, before this actually happened, in which you told me the situation and where it seemed to be heading. I remember a feeling of vast inevitability and accompanying hopelessness. One feels the pull of something one both wants and doesn't want. One knows it will have a cost both for others and oneself. Your friend leaves her boyfriend with you for the summer and you're drinking together and things happen no matter what.

Nevertheless, in my isolated little laboratory of human behavior, exercising my fictive privilege of doubtful prose, sitting in my heated den of divorce from reality, I imagined you squaring your shoulders and confessing your conflicted desire, telling him that you had feelings for him but principle prevented you from acting. I imagined you telling him that if, at some future date, he happened to be free of his commitment to your very dear friend, that then perhaps he should know that you would be willing, and waiting, and interested.


It was all so Victorian. How silly. How far from reality had I come? Did I think that a little speech given in the clarity of an afternoon could ward off all the demons of a night of drinking, loneliness and desire? I felt like the whole thing was pretty dumb and so, in my laziness and sloth, my distractedness and depression, my great self-loathing and consuming forgetfulness I sketched my ideas but never formed them into a column. I just sent you telepathic messages.

It would have been better had I written immediately to say hold off, don't do it, not yet! Grasp the reins of the moment and steer it away from the cliff!


Regret is heavy on me now -- not that I could have prevented what happened, nor that what happened is of great moment. It's just this awful habit of standing back and hesitating that pains me! As if watching a building burn, waiting to see if the upper story falls (as I feel quite certain it will!), I wait for more information.

So now what have I got to offer? Well, having acted against principle, you have a chance to take one principled act, which perhaps will square you with the fates. You can tell your friend immediately and let the chips fall where they may. You know you did a bad thing. It's likely that word will get out anyway. So do yourself a favor and sit down with your friend and tell her yourself before she hears it from someone else. It's simple: You screwed up. You have to deal with the consequences. So deal.

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