In today’s video, I talk about how to handle it when the “red flags” in your partner’s past (or present) indicate you’re not a good match moving forward, and you think breaking up is the right decision.

Read on or watch the video below to hear a few thoughts before you break up because of retroactive jealousy.

Zachary Stockill: One of the ideas that I think sometimes people misinterpret or misunderstand about me and my work is this notion that somehow I say that retroactive jealousy is always 100% irrational. “There is never such a thing as a red flag in anyone’s past, you should always stay with that person, and you should always try to fix the relationship…” And of course, that’s not true.

That’s a ridiculous idea. Sometimes there are glaring red flags in someone’s present or in their past that you should absolutely pay attention to, that are worthy of further interrogation. And sometimes, there are red flags that are probably indicative of a serious deal-breaker. In other words,

Sometimes there are red flags in someone’s present or past that might genuinely indicate you’re not a good match for each other moving forward.

And breaking up is the right decision. But before you make that decision, because it is a big life decision, any breakup or divorce, that’s a big deal… Before you make that decision, I think you should spend some time thinking about a few ideas. Today, that’s exactly what I’m gonna share with you.

Okay, so you’ve been thinking about breaking up with your partner for some time, this decision has been gnawing at you, you feel like you’ve done enough investigation, or you’ve asked enough questions, or you’ve gotten the sense from your partner that something is definitely off with their present or with their past. And you’ve made the decision to break up because of retroactive jealousy. The first suggestion I have for you before you actually bring up this topic with your partner, before you actually break up, is to make sure you aren’t ignoring all of the green flags, rather than focusing only on all the red flags.

In case you don’t know what it is: a green flag is basically the opposite of a red flag.

Red flags are potential warning signs of potentially problematic present or future behavior. Green signs are the opposite. Green signs say “go.”

Green signs are basically indications that this person has good values, you have compatible lifestyles, you have compatible life goals, they’re trustworthy, things like that. Things like clarity, emotional maturity, emotional stability, the ability to negotiate with this person, the ability to trust this person, love, and affection. These are all green flags. These are just examples.

My point is: be sure you aren’t focusing 100% on the red flags. It’s important to take note of any red flags that may come up. But we’ve all got red flags to a certain extent. I do. I’m sure you do as well. And it’s important to realize that:

You were attracted to this person for a reason.

BEFORE You Break Up Because of Retroactive Jealousy, Watch This

There was something that drew your heart to them, there was something that drew you to them in the first place. It’s important to keep that in mind. So make sure you aren’t only focusing on all the red flags; think about all the green flags as well.

Another suggestion: make sure you’re thinking hard about the difference between rational jealousy and what I would consider irrational jealousy. This is a big topic, I don’t have time to get into all the nuts and bolts of this. The point is, be sure to own what is somewhat irrational things you’re worried about that really aren’t a big deal, and differentiate that between rational jealousy.

Just as a classic example: let’s say the person you’re dating did a dumb thing one night and went home with someone who probably wasn’t a good idea. Okay? Now, no one in a relationship is going to love the thought of their partner being with anyone else, period. And if you’re so obsessed with that situation, if you can’t stop thinking about it all the rest, that might qualify as irrational jealousy as far as I’m concerned.

However, let’s say your partner has been lying to you about all kinds of things, and maybe they slept with their ex recently. Or maybe they’ve cheated on three of their past four boyfriends. To my mind, that is rational jealousy.

There’s a reason that you’re picking up on these signals…

That’s a serious red flag. Do you spot the difference? This is an extreme example, but the point is to think a little bit harder about what is irrational jealousy and what might be a little more rational.

Another piece of advice: if you’re a retroactive jealousy sufferer, remember that your next partner will also have a past. It might be less “colorful” than your current partner’s past, or it might be more colorful. It’s the 21st century, everyone’s swiping furiously on dating apps, or at least most people are. I’m not saying it’s good or bad. It’s simply a fact of dating and a fact of life and relationships in the 21st century. We’ve all got a past, or at least 99% of us. So make sure you realize that your next partner will have a past. And it might be more colorful than your current partner’s past. That’s certainly a possibility.

Another point that I feel very strongly about is: if you’re making this decision to break up because of retroactive jealousy, don’t give yourself an “out.” By an “out,” I mean, the guy rationalization that says, “Okay, well, I’m going to break up with her, I’ll try being single for a little while, but we can always get back together later.” It doesn’t work. On again, off again, relationships don’t work for a reason.

A relationship is like a plate: you break it once, maybe you can fix it, which is a big maybe. But it’s never going to be the same again

BEFORE You Break Up Because of Retroactive Jealousy, Watch This

If you break up and get back together, and you’re just torturing her and just making a mess of your life and all this chaos and stuff, it doesn’t serve anybody. It doesn’t serve you. It certainly doesn’t serve your soon-to-be ex-girlfriend or present girlfriend or whatever. It’s a messy thing to do.

I really think when you break up, you need to think rationally about this and think “If I break up with this woman, this is it. I’m not going to give myself that mental out of ‘oh, well, I can always get back with her.'” Because number one, you probably can’t. Women tend to handle breakups a lot better than a lot of men realize, I’m sure she’ll be moving on with her life faster than you think.

And secondly, even if you could get back together again, it’s never going to be the same. Don’t give yourself an out if you’re making this decision. And that’s the way to think about it before you actually pull the trigger and bring this conversation up with your partner. Before you actually talk about this,

I would say sleep on it. Don’t do anything rash. Sleep on it, and then sleep on it again.

In other words, give yourself a couple of days and a couple of nights to mull it over. You can talk to a perhaps a coach or a friend who you trust, get some feedback on what you’re feeling, and get some outside perspective that can be so incredibly valuable.

I hope you’ll forgive the fact that I’ll take a minute to plug my own services here… but I’ve worked with a lot of men in this position; dealing with breakups or mulling over breakups or thinking about red flags.

And “What is actually a red flag, and what is my intuition? What should I be paying attention to?”
It’s an area of work that I really enjoy, actually, we’re helping guys sort through their values and sort through these questions.

The point is, make sure you’re having some a sounding board, and you’re actually getting outside feedback on this. At least a little bit from someone you trust. And give yourself a couple of days to really sleep on it, sleep on it again, and really mull it over properly before you make some rash decision that you can never take back.

Finally: if your decision is final, if you really feel like this is what you need to do, there’s nothing wrong with that. Sometimes that’s the right choice. I’ve been there, you’ve probably been there too.

Sometimes breaking up and moving on is the right choice.

But I would say if you make this decision, practice kindness, practice empathy. My whole attitude for my dating life and my relationship life and all the rest is “I’m not going around trying to determine whether or not you are a good person. I’m trying to determine fit. And if we’re not a good fit, that’s okay.

The point is not to be cruel and say terrible things to this person and mess up their brain for their next relationship, maybe for the rest of their dating or relationship life. Practice kindness, practice empathy.

BEFORE You Break Up Because of Retroactive Jealousy, Watch This

You know, it’s the 21st century. Again, it’s a very, very complicated sexual marketplace out there. Dating is very complicated, in some ways more complicated than it ever has been before.

The point is, however you approach that conversation with your partner, practice kindness, practice empathy, they’re probably doing their best in life making mistakes along the way, the same as you.

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.