In today’s video, I’m going to tell you my number one tip for how to know whether you’re struggling with irrational retroactive jealousy or a genuine clash of values in your partner’s past.

So: how do you assess your partner’s past values?

Zachary Stockill: One of the things that sometimes people seem to get wrong about me and my work is this idea that somehow I tell people that there’s no such thing as a “dealbreaker” in a partner’s past, ever. “There’s no such thing as a red flag and genuine deal-breakers.” And of course, that’s not true.

Sometimes depending on your particular goals and aspirations for the relationship

Sometimes there are absolutely massive red flags, massive deal breakers.

I get emails every day from men and women, some of whom are watching these videos right now, others who are readers of my blog,, people trying to get to the bottom of their partner’s past, trying to see whether or not they’re struggling with something irrational, or they’re dealing with a genuine red flag/ deal-breaker in their partner’s past, that could be really significant for their relationship.

Moving forward, I get absolutely heartbreaking emails all the time saying these people considering breakups. They’re considering leaving their partner because of this.

How do you deal with your partner’s past values?

One thing that happened in their partner’s past is one thing that they can’t seem to let go of and frequently, these people are kind of desperate, in a sense. There’s so much nonsense out there online about the significance or not of someone’s past. There are some people who say the past of the past, doesn’t matter at all, the present is all that matters.

And on the opposite in the spectrum, there’s all kinds of men’s rights activists and all kinds of large men who say that the past is the only thing that matters, and the present doesn’t matter at all.

You need to be a detective and find every single last detail.

There’s a lot of extreme opinions when it comes to this issue. The idea of nuance is not very popular these days, it seems like everyone has a very strong and binary opinion, doesn’t matter if they know what the hell they’re talking about.

I’m a fan of nuance, and when it comes to deciding, how much your partner’s past matters, it’s a very important question.

Nuance is appropriate and even necessary when it comes to getting an answer if your partner’s past a deal-breaker.

So my number one piece of advice for anyone, male, female, young, old, anyone struggling with this question, don’t look for perfection in someone’s past. Look for patterns.

I often tell coaching clients that an event can be an exception, but a pattern is a person. There’s this line from Aristotle and it’s a nice summary of his philosophy, “we are what we repeatedly do”.

I am not saying that people can’t change and can’t change long-standing patterns.

There are all kinds of examples. For example, the guy who’s been an addict for 20 years getting clean and staying clean. People can change and people do change.

if you’re interested in risk management, looking at someone’s track record, looking at their resume, the best way you can gauge that is to look for patterns rather than perfection.

If you approach your dating life or your relationship life looking for perfection, I would love to meet this person, because I’m quite sure they don’t exist.

We have all made mistakes, we have all slipped up. It is a completely new world out there when it comes to dating Tinder, Bumble, dating apps and swiping left and right, Instagram, casual sex, and hookup.

It is a very confusing world out there in so many ways.

We’ve all made mistakes. We’ve all made decisions that we’re probably not entirely proud of. And in the Western world, you’re going to have a difficult time finding someone with zero, or slight blemishes regarding their past dating/ relationships/ sexual history.

You will drive yourself and others crazy if you go looking for perfection. Whether it’s perfection in yourself or perfection in other people.

Look for patterns, because patterns and behavior will give you a much better sense of who that person really is.

For example, let’s say you’re looking for a person to enter a long-term relationship with. You want to date someone who has some handle on relationships that have a little bit of experience, it’s not a completely new world to them.

When you want a monogamous relationship with someone with the ability to be faithful, you uphold the idea of casual sex, you don’t like the fact that a lot of people out there are hooking up. So, you meet someone you’re dating and things are going very well. You learned that they had one or two one-night stands in their 20s. But for most of their 20s and 30s, they’ve been in long-term relationships and they’re still on good terms with these exes. Today, there was no real drama, cheating, insanity, or craziness.

So, how are you going to judge them and their suitability for a relationship with you? How do you deal with your partner’s past values?

If you were looking for perfection in your eyes, you might look at the one-nightstands totally unacceptable. Looking for perfection in this regard is not serving anyone, the person you’re dating, yourself, and your aspirations.

On the other hand, in this scenario, if you’re looking for patterns, a pattern that they’re quite capable of having happy, relatively positive, long term relationships over long periods of time, those hookups or casual relationships that they had once or twice, that doesn’t really tell you a whole lot about them. That’s more of an exception, rather than a clear indication of their goals, values, and identity.

Dealing with your partner’s past values and looking for patterns, if you meet someone, and they have cheated on four of their five past boyfriends, that is a pattern.

If you’re looking for a monogamous relationship, that is something to pay attention to. That might be a deal-breaker based on you, your values, your goals, and what you want out of your life.

You should be extremely cautious when it comes to who you bring into your life. And if someone were to view that as a pretty destructive pattern, I wouldn’t necessarily think that they were making the bad decision, because that is a pattern.

The person who cheated on their past four out of five boyfriends, that person can change. But if I’m going to invite someone into my life, and I’m interested at all in risk management, there’s a good chance that person is a higher risk in certain regards than the person who has never cheated or the person who cheated once when they’re 18.

I’m not saying we should be going in everyone’s past with a fine-tooth comb, getting to the bottom of things and judging everyone harshly and unduly.

What I’m saying is, look for patterns over perfection. This will be a better use of your time.

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.