Dating After Mistakes: How to Own Your Past Without Letting It Define You
For people who’ve done deep personal work to address issues related to the past, one of the hardest parts of dating is figuring out how to talk about who you used to be.
Knowing how much to share about your past with a potential dating partner, when to share it, and how to talk about it is tricky, because it requires balancing being honest about your past while simultaneously letting yourself be seen as the person you are today.
Andrew writes:
“I’ve done a lot of personal work over the last few years and a lot of healing, thanks in large part to having a great therapist who’s helped me understand why I acted the way I did in my past relationships. I had a truly awful childhood and unfortunately, this played out with previous girlfriends as an explosive temper, manipulative behavior, and a lot of stonewalling. At times, it got very bad, so I understand why each of my girlfriends broke up with me. I’m ready to start dating again, but having to talk about why my past relationships ended scares me. Even though I want to be honest, I’m afraid of scaring off new partners by talking about things I did in the past that aren’t relevant now. How do I share these things without looking like a walking collection of red flags because of my past?”
Dear Andrew,
One of the things that I really appreciate about your letter is that it demonstrates a crucial skill you’ll need to continue to cultivate in order to share your dating history with new partners without getting pulled back into it or letting it take over the conversation.
One of the legitimate red flags that becomes apparent almost immediately in those first “getting to know you” conversations is when the topic of past relationships comes up and someone launches into a laundry list of complaints about their previous partner, explaining the ending of their last relationship by trashing their partner’s character.
That’s not to say that it’s always a red flag when someone describes the million and one ways in which their former partner was a horrible person. But it’s certainly a yellow flag that makes many people pause and proceed with caution as they get more information about what exactly went down.
That’s because when you’re first getting to know someone, they haven’t yet built the credibility and trust that’s needed to interpret their assessment of their former partners.
However, being able to talk about your own past mistakes and the harm that’s been caused, without defensiveness or blaming the other person, has the opposite effect.
Talking about your own challenges and past mistakes demonstrates the kind of self-insight and personal accountability that bode well for having a mature, healthy intimate relationship.
In other words, rather than being red flags, how you’ve described your relationship history can actually signal a green flag in the dating world.
Here’s why.
Once we are beyond the point of gaining some initial practice and experience with dating, being able to reflect on what went wrong in previous relationships, recognize and own our contribution to problems, and share this information with potential partners is really important.
That’s because it indicates the willingness to continue to do this work in future relationships. After all, given that we’re never going to become a perfect partner, self-insight and the ability to take responsibility for our own mistakes are relationship skills that we never outgrow the need for.
At the same time, I understand how intimidating it is to share difficult information about your relationship history with someone who is just getting to know you and who doesn’t yet have any context in which to put this information.
That’s why it’s so scary and why it feels like sharing your story is going to make you look like a giant red flag.
People carry this exact fear about a variety of past relationship experiences, including cheating on a previous partner, being divorced (especially more than once), struggling with addiction, being arrested, or fired from multiple jobs… the list goes on.
The reality is that the more life experience we have and the more colorful our past, the more challenging it becomes to provide a coherent and concise explanation for why things happened the way they did.
This makes sharing our history within the context of a first or second date feel high pressure. How do we give enough context for what happened without overexplaining, appearing to make excuses for past behavior, or giving too much information when someone’s just getting to know us?
Sharing painful aspects of your past, especially those that carry regret and shame, is a vulnerable experience.
And because you need to share this information with someone you don’t yet know very well, it will inevitably feel risky. You don’t have enough of a shared history to be able to predict with any accuracy how they will react when you share difficult realities about your past relationships.
The temptation to avoid disclosing unflattering details about your history is entirely understandable.
And certainly some people take this option—for example, crafting the story of a former breakup to skillfully side-step the part about how they cheated on their former partner for months before getting caught.
While this sort of approach makes it so that your past wrongdoing barely registers with the other person (if at all), it also sets up the likelihood that once the truth does come out months down the road, it will feel like a complete betrayal to the other person and call your character into question, because it will be experienced as the kind of secrecy that truly is a red flag in relationships.
The challenge in sharing serious details about past relationships with someone who doesn’t yet know you well is to balance the requirement of openness and honesty with not overwhelming yourself and your date with the excruciating shame and remorse about your past.
You need to be able to talk about what happened without becoming emotionally flooded and spiraling into self-flagellation about what happened. In essence, you have to be able to recount what happened instead of reliving it.
What is clear from your letter, Andrew, is that you are well on your way to being able to do this with a future date because, in your letter, you’ve already demonstrated your ability to talk about what happened and your insights into why it happened.
Believe it or not, being able to talk honestly about your own mistakes and hurtful behavior in past relationships is actually a sign of trustworthiness to potential new partners.
Now, being open and honest on a first or second date doesn’t translate into sharing all the worst moments from your previous relationships.
Those moments might keep you up at night and might be things you frequently revisit to work through with your therapist. These are the experiences that are most likely to trigger shame for you. They need to be held tenderly by you and anyone you share them with, which means that talking about these experiences in depth should happen only with someone who has already built trust with you.
Trust is established gradually over time through small and large interactions in which others show us who they are.
And we build trust in the same way, bit by bit, which is why it’s so important not to take a misstep early on by actively and intentionally misleading the other person about what happened in your past relationships.
Honesty is the foundation of trust.
But, as I’ve already mentioned, being open with someone new doesn’t mean that you owe them all the details of your life. It simply means that you’re able to provide, in broad strokes, the general themes of your past.
You can do this very naturally as you express your values in relationships and demonstrate your capacity for self-reflection.
You might say something like, “Since my last relationship, I’ve been doing a lot of personal work to understand how bad experiences from childhood ended up playing out in all my previous relationships. I can see now that I learned a lot of unhealthy coping skills and relationship habits that harmed my last relationship and caused hurt to my partner. When she broke up with me, it was really the wake-up call I needed to start working on these things.”
See how that kind of sharing focuses on what you’ve learned as a result of what happened, while signaling your value for personal responsibility in relationships and working to build better relationship skills? You can also see in a statement like that that it’s honest without being an exhaustive, five-hour tale of the worst moments from your past.
Calmly and confidently taking responsibility for your role in past relationship issues communicates far more about your character and relationship potential than you likely realize.
Talking about your past in broad strokes also leaves the door open for your dating partner to ask questions, gain clarity, or share similar experiences from their past relationships.
Not only is sharing openly about difficult past experiences radically different from secrecy. It’s also very different than spilling, or what’s often called trauma dumping.
Sharing requires being emotionally self-regulated, so that you can talk about what’s happened without the floodgates suddenly flying open.
Healthy self-disclosure and sharing happen in stages rather than all at once, as a relationship develops. This is intimately intertwined with the process of building trust.
You can think about it this way: Talking about your past offers a window into who you were. But it will be how you show up in the present, with your new partner, that will really tell the story of who you are now.
That’s what will really demonstrate the changes that you’ve been working so hard on in therapy.
Approaching dating with the right mindset is always important, but it’s absolutely essential when you feel sensitive and fearful of rejection because of elements of your past.
First, I want to caution that rejection is a very real risk that’s baked into the experience of dating. There’s no way of getting around it.
Developing rejection resilience is important when you’re putting yourself out there again.
And one piece of this is to not let one person’s response to you become a global prediction of how others will respond. While it’s natural to feel apprehensive about sharing your history with another person, it’s really important to work through a false belief like, “If I share this and the other person reacts badly, this means my past makes me undesirable or unlovable.”
One person’s reaction will never be a universal verdict on your worth, because we’re a tremendously diverse species… and there’s not a single thing in life that everyone agrees on.
At the same time, it’s important to leave space for honoring the past histories of your dating partners.
This means that if you are starting to date someone with a painful history that matches your own, it may not be a good fit. For example, people who’ve been deeply hurt by a partner’s cheating may not want to take a chance on someone with a history of infidelity.
Or someone who grew up with an explosive parent and who’s been in a relationship with an explosive partner may know themselves well enough to know that they’d be too anxious and fearful of upsetting you to make a relationship with you workable.
Dating involves discernment of fit for both individuals.
Lastly, let’s talk about what you can realistically expect from yourself in a new relationship, given all the personal work you’ve done. Here’s what I always tell individuals I work with.
Individual work will take you a long way, but when it comes to relationship issues and interpersonal dynamics, individual work can’t take you all the way.
There are some patterns and dynamics that we don’t get the opportunity to work on when we’re single because they never come up. Assume that you are going to confront some of your past relationship patterns again in a new relationship.
This will be your opportunity to get the practice you need to build new relationship skills.
You’ve already been developing the skill of self-insight that you’re going to need to apply when things happen in a new relationship that hook you in and cause you to replay old emotional responses. That’s absolutely okay.
When it comes to relationships after trauma, my philosophy is that it’s less important to focus on what happens than to focus on what happens after what happens.
In other words, expect that at times your trauma will get the best of you in the moment. But what do you do next? Do you brush it under the rug and hope to do better next time? Obviously no. You learn how to make a repair with your partner.
You use your practice of self-reflection to pinpoint exactly where you got triggered, you think about what you would do differently if you could do it over again, and then you share that with your partner.
This is how we get better in relationships.
This is how we heal the past and create a future that looks like what we want instead of what we know.
And Andrew, here’s my wish for you. May you approach dating this time around with the knowledge that you have never been a better potential partner than you are right now. May you have the kinds of conversations with potential partners that help you see that your past doesn’t disqualify you. And may you really, truly know that being ready to date isn’t about having an unblemished past. It’s about having a deep relationship with it.
~Angela
Ask Angela is an advice column dedicated to the topic of having fulfilling relationships after trauma. Click HERE to submit a question for Angela.
DISCLAIMER: this content is intended for informational purposes only and does not constitute professional medical or psychological advice, diagnosis, or treatment. Always seek the advice of your physician or other licensed health care provider with any questions or concerns you may have regarding a medical condition.
about angela Amias, LCSW
Angela Amias is a therapist, writer, and educator whose work focuses on healing relationship trauma and creating more meaningful, fulfilling connections. She has worked with hundreds of individuals and couples to help them understand how early experiences shape their relationships and to find a path toward deeper connection with themselves and others.
Her work is grounded in the belief that even painful experiences can become part of our growth, and that relationships can be a powerful place for healing and transformation.
Angela has been featured in publications including Today, Oprah, Cosmopolitan, Well + Good, The Independent, Salon, Inc., Forbes, Toronto Sun, Women’s Health, and Refinery29.
