How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous!

Dear How to Do It,

My wife and I have been married for 20 years.

For 19 of them, I have been having multiple affairs. My job requires a lot of travel, and as such, I have mistresses in many different states and even in other countries. They all know I’m married, and we keep our liaisons confined to when I’m in their area. As of late, I’m starting to feel a bit guilty. Should I stop seeing the other women, or just keep on keepin’ on, given that nearly two decades have passed and my wife doesn’t have a clue?

—Time to Settle Down?

Dear Time to Settle Down,

Help! My Friend Helped Me When I Was at My Lowest. Now I Want to Ghost Her. This Content is Available for Slate Plus members only My Girlfriend Wants to Break One Of My Cardinal Rules of Adulthood My Daughter Can’t Seem to Get Behind a Basic Part of Growing Up. It’s Become a Daily Battle. I’m Planning My Wedding. I Don’t Know What to Do About My Fiancé’s Brother.

I mean, OK, yes—the short answer is that yes, you should cease your affairs in as kind and clear a manner as possible. That said, if you were significantly motivated by sentiments of what’s “right” and “wrong” in this specific area, you wouldn’t have been engaging in infidelity for nearly two decades. It would be easy to say, “Stop that, because it’s wrong,” but if you were prompted to write this letter by a momentary whim, that is unlikely to occur.

I’m curious what, after 19 years of affairs, is causing you to feel this guilt. I’ll admit some of that curiosity is personal, but I do have a hunch that this information will be useful to you as you think through your situation. Did something happen that prompted you to consider your wife’s possible feelings? Or made you begin worrying about ramifications in a way that you hadn’t been concerned about until now? Some internal shift toward a different moral code?

I’m also curious, since you started these liaisons a year after entering your marriage, what the appeal and justifications were at that time. Are there now reasons to stay faithful that are more compelling to you? Do the ways you excused your actions at the time now feel less valid? Is it simply that, with age, the raw appeal of sowing your oats has decreased? Get a deeper understanding of what has changed, and let that guide your choices moving forward.

—Jessica

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