Dear Anna,
I’m a 34-year-old woman who’s been in a relationship with my boyfriend for almost four years. We’re serious—and lately are talking more and more about marriage. But something from my past has been weighing on me, and I’m struggling with whether or not I should tell him.
About five years ago, in a previous relationship, I cheated on my then-boyfriend. It was a rough time in my life; I was unhappy, and the relationship was already falling apart. While I deeply regret what happened, I’ve grown a lot since then, and I’ve never even come close to doing anything like that with my current boyfriend.
We’ve built something solid, and I’m scared that if I tell him about my past infidelity, it might change the way he sees me. But at the same time, I don’t want to keep secrets from him, especially as we’re talking about such a serious future together. I want to be open and honest, but I also don’t want to bring unnecessary pain into our relationship if it’s not relevant anymore. Is it something I should tell him? Or should I leave the past in the past and focus on the relationship we have now?—Torn About Transparency
Dear TAT,
You clearly care deeply about your boyfriend and your relationship, and that’s the most important place to start. The fact that you’re grappling with whether or not to share something from your past that you’re not proud of shows that you value honesty and transparency.
And it’s also understandable that you’re afraid of the potential fallout. The fear of being judged for past mistakes is real, especially when those mistakes involve infidelity—a topic that stirs up a lot of emotions for people.
The real heart of your dilemma is this: Does bringing up your past infidelity help or harm your relationship now? That’s not an easy question—and, indeed, it might be both! But I think it’s worth unpacking a few things.
First, the truth is never simple, but it’s also never inherently destructive. Context matters, and so do our intentions. According to some research, our intentions are more important than the truth in question. The most harmful lies are usually the ones told to serve our own interests while disregarding the well-being of others.
In your case, you don’t appear to be motivated by selfish interests—you’re not trying to absolve your guilt or get back at him for something. You want to tell your boyfriend because you want him to know who you are, even the less flattering bits.
Plus, it sounds like your past infidelity was a product of a very different time in your life. You’ve reflected on it, learned from it, and grown into a different person since then. That’s important. You’re not just confessing a mistake—you’re offering your boyfriend a fuller picture of who you are, including the things that shaped you into the person he loves today.
What if telling him about this mistake shifts how he sees you? What if he can’t let go of it, even though it’s in the past? These are valid concerns. However, when we withhold parts of ourselves from the people we love, even with the best intentions, it creates a subtle barrier. Your boyfriend deserves the chance to know all of you, including the person who made mistakes and learned from them. And the reverse is also true: You deserve to be fully known.
That said, timing and delivery are key. This conversation shouldn’t come out of nowhere or during an argument. Approach it with vulnerability, and make it clear why you’re sharing this now—not to stir up old wounds, but because you want to build your future on a foundation of honesty. You can say something like, “There’s something from my past that I’ve been reflecting on, and I feel it’s important to tell you about it. I’ve grown a lot since then, and I’m committed to our relationship, but I don’t want to keep any secrets from you.”
Your boyfriend may need time to process this. He may have questions, or he may surprise you by recognizing that your past doesn’t define your present.
Ultimately, the goal here is not to focus on past mistakes but to allow space for both of you to see each other fully—flaws and all—and continue growing together.
Wishing you clarity and connection.
Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter, or check out her books!
This column originally appeared on The Chicago Tribune.
