In today’s video, I’m going to answer a viewer question: “My girlfriend’s past is a dealbreaker. Should I try to work through this, or leave?”

Read or watch below to hear my response to a viewer who tells me “my girlfriend’s past is a dealbreaker.”

Zachary Stockill: I received an interesting and thought-provoking comment on Instagram recently that I just had to take a minute to respond to. A commenter wrote:

“My girlfriend’s past is a dealbreaker. Do you think I should try to work through this?”

And that’s exactly what I’m going to talk about in today’s video.

First off, thanks for your comment. I have a lot to respond with. 

The first thing I’ll say is you are not clear if this is a dealbreaker or not. Because if you were clear that this is a dealbreaker, you wouldn’t be messaging me, you wouldn’t be struggling. You would have moved on already. Because the whole idea of “dealbreakers” is that they’re very kind of cut and dry. They don’t require a tremendous amount of mental strain.

But the trick is, you need to know your personal boundaries, you need to know your personal values, before you can decide “my girlfriend’s past is a dealbreaker.” 

And you need to know your personal dealbreakers in the first place. So the fact that you’re asking me this question to my mind says you aren’t 100% clear if your girlfriend’s past is a dealbreaker.

Because the whole idea of a dealbreaker is it breaks the deal. It’s relatively unambiguous. And the fact you’re not clear about that says to me should give the relationship a little more time.

A better question I would pose back to you is: is it worth challenging your preconceptions? And I think the answer to that is yes. Because again, to my mind:

The word dealbreaker has a certain clarity and finality to it. It’s very cut and dry. 

And if you’re struggling with this question, you may be in a process of unraveling some of your pre-existing notions about women and sex and dating and relationships. To my mind, you’re probably a younger person if you’re going to write a question like this. And you need more time to sort through these feelings, to sort out your personal boundaries and values, before you make a decision like ending the relationship. 

Another question? Is it worth opening up your mind to new perspectives and possibilities? To my mind, the answer to that question is an absolute yes. This is a time for learning, for unlearning. This is a time to get new clarity and perspective about who you are as a man. And, what you want out of your woman living out of your dating life, out of your relationship life. It’s time for you to set relationship goals for yourself. But above all, it’s time for you to use this opportunity to get to know yourself better. 

Because once you attain the necessary self-knowledge, questions like this don’t become an issue for you anymore. It is because you know yourself so well. 

You know what you’re willing to tolerate. You know, you’re not willing to tolerate, and you’re not going to compromise on that. 

So is it worth challenging your preconceptions? Yes. Is it worth opening up your mind to new possibilities? Yes. But is it worth compromising on your deeply held, non-negotiable relationship boundaries and values? To my mind? The answer to that question is a firm no.

People who compromise their relationship boundaries are some of the most miserable people in the world.

People who compromise on who they are and what they truly want out of life and out of a relationship? These people are often the most miserable people in relationships because they’re waiting for their partner to change. They enter a relationship with the idea that “this person is great. But if I can just tweak this one thing, then they’ll be perfect… Oh, things will be perfect when x happens, I want the perfect relationship, or She’s perfect for me except for X, Y, and Z…” You get the idea. If you watch my channel for a while, you know that…

The word that I think is the most dangerous for any kind of relationship or dating is the word “perfect.”

my girlfriend's past is a dealbreaker

Perfection does not exist. However, one thing that definitely does exist is degrees of suitability. And that’s what you have to spend the time to figure out: are your feelings rational or are they not? Or does your girlfriend compromise or violate your deeply held, non-negotiable relationship boundaries and values? I can’t answer that question for you because your values are not my values, and vice versa. 

And trust me, once you do arrive at these answers, it makes your dating life so much easier. 

Because it becomes very easy to either qualify or disqualify certain people when they enter your life. It becomes clear to you, very early on, they are simply not a good fit. 

Another piece of advice I would offer to you as you work through this question about your girlfriend’s past is: whether it’s something you can live with someday, or whether it’s something you fundamentally can’t. As you work through this question, try to remember to practice empathy, kindness, and respect. 

Because the whole goal of engaging in introspection, trying to get to know yourself better, trying to discover your relationship boundaries and values, your relationship goals, and things like that…

The goal of this process is trying to determine fit. You’re not trying to determine whether your partner is a bad person. Or whether anyone else is a bad person. You’re not trying to determine whether you’re a good person. It’s not so much an exercise in trying to determine moral superiority because what’s the point of that? The point is simply about fit

You’re trying to see whether you’d be a good fit for each other. And whether you have a relationship future.

my girlfriend's past is a dealbreaker

Above all, I would say, don’t punish your girlfriend for her past. It’s a terrible move. You’ll feel guilty about it. If not now, soon in the future.

And be 100% clear that it’s a dealbreaker by your standards before you make the decision to leave. But at the same time, don’t put off your decision forever. Because you don’t want to drag this out forever and hurt your girlfriend unnecessarily. And you also don’t want to waste your time or her time.

But, if you want help sorting up this question, whether you are the comment writer watching this or anyone else watching this video…

This month, I’m celebrating the release of my all-new masterclass on overcoming retroactive jealousy. This was designed specifically for RJ sufferers who have questions about their partner’s boundaries and values, and who wonder whether their past is a dealbreaker or not. 

My new masterclass is called “The Path to Peace.” It has more than two and a half hours of all-new exclusive content, exclusive exercises you won’t find anywhere else, not my other online courses, nor on my YouTube channel.

If you are struggling with your partner’s past values, if you have serious questions about the future of your relationship, whether they share your values, I hope you’ll take a minute to check out my new masterclass “The Path to Peace”.

Zachary Stockill
Zachary Stockill

Hi! I'm a Canadian author and educator whose work has been featured in BBC News, BBC Radio 4, The Huffington Post, and many other publications. I'm the founder of, the author of Overcoming Retroactive Jealousy and The Overcoming Jealousy Workbook, and the host of Humans in Love podcast.