My girlfriend and I broke up a month ago. We had been dating for two years when things went bad, and we decided to call it quits. I had a one-night stand during our break, but I have been communicating with my ex again, and it seems like we both want to get back together at some point. Should I tell her about my one-night stand immediately, or should I wait for her to ask about it?
— Getting Back Together
Dear Getting Back Together: I vote for keeping that information to yourself. You say that you broke up with your ex before this happened, which means that you did not break any covenant of fidelity to her. Revealing that you were intimate with someone else — even if it was only for one night — is likely to trigger all kinds of worries and emotions. That isn’t necessary.
If the two of you are seriously interested in trying to be in a relationship again, talk about what you want, and be honest about what’s important to you. Be honest about your priorities and needs. Give each other space to talk through your hopes and fears. Figure out if there seems to be a way forward for you.
In the context of these talks, if it seems natural to reveal what happened, you may do so. But it is not necessary or wise to volunteer that information at the start. Having a one-night stand or even dating for an extended period of time when you were not together is separate from your relationship.