That Age-Old Question: How Much Sexual History Should I Share?


Heidi Younger

The “Dear Sugars” podcast is an advice program hosted by Steve Almond and Cheryl Strayed. The audio contains more letters; submissions are welcome at If you’re reading this on desktop, click the play button below to listen. Mobile readers can find “Dear Sugars” on the Podcasts app (iPhone and iPad) or Radio Public (Android and tablet).

Dear Sugars,

When is “not telling” lying? I’m 32 and engaged to a man I’ve been with for nearly three years. I love him more than words. Among my circle of friends, there are two men I slept with in my 20s. In each case, the sex was casual and short-lived and we went on to be nothing more than great friends. My fiancé now knows these men, too, but he doesn’t know I’ve had sex with them.

With our upcoming wedding, I feel the need to come clean. I want to be honest with him, and I also feel bad that he doesn’t know about my past with these men while several of my longtime friends do. I’m not ashamed of what I did, but if I tell my fiancé, I’m afraid he’ll be hurt that I waited so long to tell him. If I don’t tell him, I feel like I am hiding things and that’s not the way to start a healthy marriage. What should I do?

Truth Teller

Steve Almond: You’ve told us quite clearly what you need to do, Truth Teller: I feel the need to come clean. And you’ve even told us why, because hiding things is “not the way to start a healthy marriage.” You happen to be absolutely right on the latter point. It’s true that your fiancé might be upset. If that’s the case, by all means acknowledge his feelings, and express the regret you feel about not telling him sooner.

But it’s also important to keep straight in your own mind and heart where you feel you’ve erred. I hope it’s not in the fact that you had love affairs before meeting your fiancé, because most of us are in the same boat — including him, I suspect. (That’s how it works among most consenting adults.) There’s also nothing wrong with you befriending old lovers. Lots of people do. If there’s a betrayal here, in other words, it stems from the way in which you ignored your instincts. This conversation, difficult as it might be, is a chance to remedy that, and to build a greater sense of trust with this man, whom you clearly adore.

Cheryl Strayed: The reason that this question is weighing on you is that you know the answer. You aren’t so much wondering what to do as you are dreading what you know you must do. You should absolutely tell your fiancé about your history with these two friends. You told a lie by omission because at the time — early in your romance with your fiancé — omitting the truth was easier than telling it. Don’t beat yourself up about that decision; you aren’t the first person who opted to tell a lover less rather than more about your sexual history.

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