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

This post was originally published on this site
The Sweet Spot

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.

Perhaps if you’d told your fiancé about your past with these men, he wouldn’t have wanted to become friends with them. Perhaps he wouldn’t have been fazed at all. You don’t know. You now have the opportunity to find out. It’ll likely be an uncomfortable conversation. Your fiancé may be angry or hurt that you didn’t tell him sooner, but neither of those things are good reasons not to be transparent about your past with a man you intend to marry. If anything, it’ll be a healthy test of your skills as a couple when it comes to resolving conflict.

SA: You held back on telling your fiancé about these ex-lovers because you feared he would be hurt or angry or both, and that he might judge you. As Cheryl suggests, that’s a very real possibility. But here’s the deal: Every long-term relationship gives rise to conflicts, small and large. The real question is whether you and your fiancé can work through these conflicts in ways that are ultimately productive, that allow you to be more honest and forgiving of each other when the next clash arises.

The longer I’ve been married, the more obvious this has become. When my wife and I dodge conflict — when we suppress feelings of disappointment or frustration — we wind up sandbagging each other. We retreat into defensive emotions such as contempt and self-pity. We stop listening to each other and instead spend our mental energy trying to win the argument rather than suing for peace. I’m not trying to scare you, Truth Teller. I’m trying to exhort you to recognize conflict as an inevitable part of the marital arrangement. The love affairs that endure and thrive are not those in which the partners always agree, but those in which the partners have learned to respect and esteem each other in the midst of disagreement.

CS: Years before I met him, my husband had a brief sexual fling with a woman who is now a friend of mine (and his). He told me about his history with her soon after I met her and, not long after that, I told her I knew she’d slept with my husband back in the day. She immediately said she’d wondered if he’d told me, and then we laughed with relief. We were both glad it was out in the open. No secrets. No drama. No harm done. Nothing had to be concealed because everything had been revealed. It’s almost always the way to go. And it’s never too late to do it, though it becomes more complicated the longer you wait.

The truth you need to tell, Truth Teller, is less about those long ago sexual dalliances that meant little to you than it is about the kind of relationship you want to build with your partner. Is it one in which you avoid the hard conversations or have them? Is it one in which you and your partner claim responsibility for mistakes or rely on passive deception in order to cover them up? Is it one that takes the easy way or the right way? You don’t need us to tell you the truth about what you should do. You know what it is. Deep breath. Steady mind. Start talking.

Related Coverage

  1. Modern Love: He Showed Me His Tiles, So I Showed Him Mine Dec 8, 2017
  2. From Ho, Ho, Ho to No, No, No! Office Parties Feel the Chill Dec 8, 2017
  3. Dear Sugars: Listen to ‘Dear Sugars’: Just Say It Dec 9, 2017
  4. The Sweet Spot: Love the Club, Hate the Cocaine (and the Lies) Dec 5, 2017