I’ve read your advice about what a woman should do when she has found her significant other cheating/sexting/lying. Now I need your help because I have done those things and she is ready to walk. I have a history of this and have even gotten the help of a psychologist in the past. A few months ago when my girlfriend and I were doing long distance—and very close to moving in together—I became depressed and lonely. I used a fling as a crutch. It didn’t lead to sex, but it was a mistake and I knew it. I had a shock to the system and realized that I love my girlfriend and want only her. We have been living together for two months now. She is the love of my life and I am so glad I made the move. However, she recently found out about my mistake and has lost all trust in me. To make matters worse, I tried to soften the blow by not disclosing everything when she asked. I figured she was already in pain and I didn’t want to hurt her even more. That was dumb; she found out everything and now it’s worse. How does she build trust in me when I have done this before? I can promise until I’m blue in the face, but how does she know I mean what I say? Or have I hurt her so much that she can’t?

He Said: So the problem here, as usual, is not your emotional/sexual infidelity. That happened, and it happened for a reason that you should work on getting to the heart of. In the big scheme of things, it is trivial. It is highly unlikely, after all, at either of you can manage to be entirely faithful, emotionally or otherwise, for your entire time together. The problem of course is dishonesty. You are unable to own up to your need for more, whether that need is healthy and credible or not. And that leads to deception, for which your girlfriend is rightfully hurt and mistrusting. I don't think you can ever promise her the kind of emotional monogamy that simply does not exist in the real world. However, you can work together to find ways of letting each other know the complexity of your desire and need for affection over time, and with a focused effort not to take such honesty as evidence of some kind of personal failure of love and loyalty, you can work things out together. The most important thing is to never pretend that everything will be fine from here on out, that you are now the perfect lover, which only sets you up for failure all over again. Gradually, over time, that kind of brutal honesty is most likely to win her trust back.

She Said: I’ve edited down your question for the sake of space, so the readers will have to trust me when I say I think you doth protest a bit too loudly. Putting myself in your girlfriend’s shoes, I would not be all that interested in your promises and exclamations of love. What would interest me more are the conclusions you came to with the psychologist over this pattern of betrayal in your relationships, why you think you once again indulged it after becoming aware of it, and—most importantly perhaps—the bottom-line question: Are you sure you want to be monogamous? Because you can’t have it both ways. Monogamy at the beginning, or when things are going great and you feel “in love,” is not exactly monogamy, or at least not the bulk of it. It’s simply part and parcel of the hypnotic fairy dust that our hormones drown us in. The essence of monogamy—both its sacrifices and its deep rewards—emerges when you are separated from your partner, lonely and depressed, disappointed in them, doubtful. When one of you is ill, or bankrupt, or has gained 40 pounds, that’s when the meaning of monogamy becomes clear. I’m not trying to scare you. I want you to think this through. Do you really want the path of monogamy? Counter conventional thought, it is not the only path, especially in San Francisco, and it is not necessarily a higher form of relationship than one that allows both partners the occasional fling, emotional or sexual.

Be honest with yourself, and with her. If, in the end, you want to keep working toward monogamy—for that is what it looks like you’re doing, and in this light your emotional fling is a step forward from the sexual ones of your past—then tell her what you learned in your therapy and that you are willing to return to it. Tell her what this latest fling has taught you about yourself. She may want to have access to your phone and emails after this; you must decide if you’re okay with that. Lastly, begin to realistically frame infidelity to your own commitments as an act that hurts not only your partner, but yourself—emotionally and spiritually. Whether or not you two break up over this, you will suffer its effects for a while to come. That's good. One of the best paths out of a habit of betrayal is to embrace the suffering you’ve brought on yourself, and let it teach you.

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