Today’s reader email comes to us from Jack, who worries that his boyfriend’s exes are really “better” than him. Jack writes:

I often feel like I’m not enough for my boyfriend. He’s had so many sexual partners, and when I look at myself, I feel like I am definitely less good looking and much less attractive than my boyfriend’s exes. I’m afraid I might turn out to be not enough. Does this have to do with retroactive jealousy?

Transcript below

Zachary Stockill: Thanks for your message Jack, and the short answer is yes. I think this is a pretty classic example of retroactive jealousy if you have a partner who’s had a rather active sex life.

There’s a lot to dig into here, but I’ll just start off by saying that this is definitely related to retroactive jealousy. And, everything I talk about on this channel, in my website, my guidebook, my online course, I mean this is pretty standard stuff.

But I want to introduce an idea today that I’m not sure I’ve talked about publicly. I get into this with private coaching clients sometimes. I get into this with students taking my course sometimes. But, I’m not sure I’ve talked about it on this channel.

The idea is when we question our partner about their past or when we look to them for reassurance. Or, when we do all of these habits, all of these really negative things that we associate with retroactive jealousy. When we act in these ways in front of our partner, the message we’re sending to our partner is:

You’re a liar. I don’t believe you. When you tell me I’m the best for you, I’m attractive, sex is great… When you tell me how much you love me…

Whenever we question your boyfriend about your boyfriend’s exes, what we’re saying to them, in essence, is “you’re a liar.”

So for anyone watching this who’s maybe done that before, and by the way I used to be the master of this.

So I certainly include myself in this category, but for anyone watching this who’s behaving this way before, ask yourself: if I was on the receiving end of that, how might that make me feel?

How might it make me feel to be constantly told by my partner that they don’t trust me? They don’t believe me when I reassure them. When I talk about how much I love them, when I do all these things for them they keep rejecting on some level. They keep questioning it or looking for more reassurance, and they don’t trust me… how might that make me feel?

I would imagine if you’re anything like me, at a certain point you come to the realization that that’s pretty unattractive behavior, and it’s insulting to feel like the person you love most in the world thinks you’re a liar.

They don’t trust you, they don’t believe you.

man looking down

So anyone watching this who’s struggling with insecurity around retroactive jealousy, constantly looking for reassurance about their boyfriend’s exes, not trusting their partner when they give you compliments, not trusting your partner when they say that you’re the best for them or all the rest… just remember that everyone has their breaking point.

I promise you I’ve got the emails to prove it.

Everyone has their breaking point, and at a certain point your partner will not be able to take being made to feel like a liar anymore.

It’s really insulting. It’s really hurtful, and at a certain point unfortunately they’re likely to just reject you and walk away, and confirm all of your worst fears and doubts about yourself simply because they’re tired of being made to feel like a liar all the time.

So when people look to me for advice on overcoming insecurity about a boyfriend’s exes, overcoming feelings of inadequacy–the thing that I tell them all the time is it has to come from within. I mean, you need to believe it for yourself.

As great as it can be to hear nice things from your partner, and for them to say all kinds of nice things about you, and provide this reassurance…. when it comes to retroactive jealousy, that isn’t enough. It really, really isn’t.

It’s a big reason why I really try to ram home the point in my online course and my guidebook that retroactive jealousy is your problem to solve, and your partner can’t solve this problem for you.

There’s a lot to be said about the art of building self-esteem.

There are a couple of really good books on this topic.

But above all, remember that every time you reject your partner’s love, every time you reject their words of reassurance, you’re telling them that they’re a liar and that’s really unattractive. It’s really unhelpful, and it’s only pushing them away from you.

Thanks for watching this video. If you’ve got any value from this, please be sure to click the like button below. Also, be sure to subscribe to my channel. I’ll talk to you again very soon.

Click here to learn more about getting past your partner’s past, and overcoming retroactive jealousy.

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.