Jealous Boyfriend? 3 Reasons Why He’s Hung Up On Your Sexual Past

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by Jeff Billings in Retroactive Jealousy Blog
August 16, 2016
jealous boyfriend

Being in a relationship with a jealous boyfriend can be a debilitating and confusing experience. But don’t give up hope just yet.

He may be acting irrationally with his retroactive jealousy ocd.

He may be driving you crazy by obsessing over your ex hook-up buddies or boyfriends.

But believe it or not, there’s a reason for this.

Actually there are at least three reasons, and in this post I want to let you in on what they key ones are.

Hopefully then you’ll be able to see things a bit more from his perspective and understand just why you’ve ended up with a jealous boyfriend.

Here are three main reasons why your boyfriend is jealous of your romantic or sexual past.

1. A Jealous Boyfriend Often Has A Madonna-Whore Complex

The Madonna-whore complex is sometimes known as the Madonna-whore syndrome, or simply, Madonna syndrome.

This is one of the primary reasons why he’s so upset about your sexual past.

It’s when a man divides women up in his mind to belonging to one of two categories:

1. Saints

2. Whores.

Yes, it’s not the most enlightened way of thinking, I admit, but it’s part of the reason why he’s seeing your sexual history in such a negative light.

He can’t get his head around the fact that a woman he’s close to (you) can be both someone he sees a future with and someone who’s “slept around a lot”.

It’s a complicated Freudian thing which all goes back to his mom, of course.

You don’t need to know all the details, thankfully.

Just get him to read my post on the Madonna-whore complex and he should understand more where his judgment is coming from.

2. You’ve Given Him Too Much Info

Yes, I get it…

We all have “the talk” when we meet someone new.

But sometimes guys ask things when they don’t really want to know the answer.

And sometimes women tell them things they didn’t ask to hear.

This is what happened in my case.

I stopped asking girlfriends about their sexual history back when I was a teenager.

But when I met my current girlfriend she told me all about it without me asking.

She didn’t know of course that all those stories about her former “friends-with-benefits” and one-night-stands were burning me up because I didn’t tell her they were.

I kept quiet.

And then the more she told me, the more I wanted to find out.

So I started asking her questions.

And before I knew it I’d descended into my own private retrograde jealousy hell.

Remember this:

Jealousy kills. But the ammo is information.

So try to refrain from telling him anything he doesn’t need to know.

Details about your sexual history will only add fuel to the fire of his retrospective jealousy.

Here’s a post I wrote for What To Do If Your Man Is Jealous Of Your Sexual History

This article goes into more detail on how to handle a jealous boyfriend who’s obsessed with your sexual past.


His Sexual Jealousy Has Been Hardwired Into Him By Evolution

Men often go into caveman mode when confronted by any type of threat to their sexual possession of their woman.

So his knowledge that you once had sex for the hell of it with a variety of random guys has triggered a deep caveman-like response in him.

You see, he’s been hardwired by evolution to hate any guy who once had sex with his partner.

It makes him feel insecure.

Like you might run off and have sex again with the next Ryan Reynolds lookalike who comes your way.

Which of course is nonsense.

Just because you used to enjoy casual sex, doesn’t mean you still want to enjoy it again now that you’re in a relationship.

And he knows this. Kind of.

Well, intellectually he knows it, but emotionally because of the deep hardwiring thing he can’t shake his jealousy of your sexual history.

This all relates back to questions of fatherhood and an insecurity that he might end up bouncing a baby on his knee that later turns out to belong to someone else.

Here’s a post you should get him to read called What Causes Retroactive Jealousy? Here’s the Answer which explains all this in more detail.


Get your jealous boyfriend or jealous husband to read the posts I suggest and also maybe take a look at your own behavior.

Try not to poke the bear so to speak, but talking about your past or joking about the great sex you had in the back of Mikey’s car.

Let me know in the comments section how you’re coping with having an obsessive boyfriend or jealous husband.

What strategies have you used to try and cure his retroactive jealousy?

Have you considered breaking up over it?

Let me know!

And don’t forget that you can point him toward my course “Overcoming Retroactive Jealousy 101” that will help him beat retroactive jealousy once and for all.


And give you both some peace of mind 🙂


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