Dear Kiki: I think my friend’s husband is trying to start an affair

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Dear Kiki,

One of my best friends was recently married to a wonderful man who I think is a perfect fit for her. Although he’s very shy, after the wedding he began reaching out to me via Facebook Messenger in order to — as I first assumed — get to know me better. However, the conversation on his end soon shifted from typical banter to topics that make me feel uncomfortable, such as statements about his “endowment,” questions about my sexual history and requests for advice regarding his personal sex life. Many of these messages arrive out of the blue while he’s at work or after his wife has gone to bed.

I have no feelings for him other than those of a friend. I’ve always tried to be nice and understanding, while subtly shifting the conversation back to his wife or on to other topics. He has explicitly asked that I keep our chats confidential — including from his new wife — which has also begun to worry me. I’m afraid that she wouldn’t approve.

Is he trying to start an affair? I want to believe that it’s nothing, or that he’s simply lacking a guy friend to ask those types of questions. I’m afraid that revealing our conversations might jeopardize both our friendship and their marriage. What should I do?

Un-Marriaged Counselor

Dear Counselor,

Let’s forget for a second that this man is your good friend’s husband.

He is initiating conversations that make you feel uncomfortable, and he is asking you not to tell anyone about them. That is not OK. In-and-of itself, that is unacceptable behavior.

If he is indeed simply turning to you in the absence of any other friend to turn to, that would require that he considers you a friend — in which case the last thing he should want is to make you uncomfortable. Call his bluff: Make your discomfort known to him, unequivocally. If he persists, then he is not being an awkward friend, he is being emotionally abusive and manipulative.

I know your instinct is to protect your friend and her marriage, but this is a case where you need to put your own oxygen mask on first. Forget what he may or may not be “trying” to do. Forget any desire to be nice to him; be forthright instead. You deserve to have your mental and emotional space honored.

Enact clear boundaries that any good friend would willingly respect — and in case he is just friendless and awkward, have the names and numbers of a couple of good therapists on hand, so you can suggest an alternative to his choice of turning to you with questions.


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And Counselor? I’m sorry to say this, but keep the chat transcripts, for a while, anyway. Until you see how this pans out. Because there is a worst-case scenario here, and that’s him taking your healthy boundaries as rejection, reacting with anger and attempting to come between you and your friend as retaliation.

In that instance, you have my full permission to go nuclear. Tell your friend the whole story, show her your evidence, be prepared that she might not believe you — and then step back and wait to catch her when she falls away from him, whether that be in a night, a month, a year or a decade.

xoxo, Kiki

This article was originally published in Little Village issue 268.

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