In today’s video, I’m going to respond to a retroactive jealousy sufferer, who’s confused about her boyfriend’s past in hookup culture. She’s wondering if she should dive in and pursue a similar kind of lifestyle in the hope that this will cure retroactive jealousy.

How to deal with your partner’s history of casual sex and retroactive jealousy?

Zachary Stockill: We currently live in the age of Tinder. Tinder, Bumble, and all these dating and hookup apps are all around us. We’re being presented with these images and narratives around hookup culture. And it seems like everyone around us is swiping left and right and having all these casual encounters.

This can be confusing to a lot of people who are not necessarily into that kind of thing.

So I received a comment on a video lately that I thought was interesting. Cat writes…

Could you make a video on struggling with retroactive jealousy, but thinking maybe we should participate in hookup culture, thinking it might cure the issue?

I’ve been in multiple relationship configurations. Over the course of my life, I’ve been in very strict monogamous relationships. I’ve been dating multiple women at the same time. I’ve had some experience. If you haven’t had any kind of casual sexual relationship, and then all of a sudden, you had some kind of casual encounter, the # 1 realization you would have is, “this isn’t a big deal at all”.

Casual Sex and Retroactive Jealousy

I don’t mean to say that it isn’t a big deal in the sense of the moral implications. But, casual sex, it’s not all it’s cracked up to be. It’s often not very satisfying. It’s kind of shallow, at least a lot of parties often feeling kind of just drained and uninspired.

There’s a huge difference between having sex in a committed relationship with someone you love and having casual sex.

So, how to properly deal with casual sex and retroactive jealousy?

I get a lot of emails from retroactive jealousy sufferers who don’t have a lot of experience with one-night stands and hookup culture, and they think that if they simply had some of that experience, this would solve their problem.

It can be a good thing for some people to have a range of experiences so they have that insight and perspective. But, if you go out, and all of a sudden start sleeping around or you go on Tinder and start swiping madly, I don’t think this is going to lead to any grand insights into sex, dating, or relationships necessarily.

This will not make an enormous difference in curing retroactive jealousy, insight, and perspective.

There are other ways to gain insight and perspective, such as talking to friends who’ve had hookups, talking to a therapist or

I don’t think you should ever push yourself to have any kind of relationship, dating, or sexual experience that doesn’t feel like it’s something you genuinely want for yourself.

Another question I get from retroactive jealousy sufferers…

Should I break up with my girlfriend and go sleep with 10 other women and then come back to her because this will solve my retroactive jealousy?

Retroactive jealousy is a very obnoxious and often illogical little issue.

And just looking for surface level solutions, like “maybe I’ll have some casual sex, or I just need to sleep with more people than my partner”. They don’t really work. They don’t satisfy that urge. They’re not going to be a long-term solution to this problem.

Casual sex and retroactive jealousy require some deeper investigation and a more varied approach and looking for a quick fix such as sleeping with someone else, or cheating on your partner is only going to make things worse.

It’s not a long-term solution.

This hookup culture that we live in right now is doing a lot more harm than good to a lot of people. I speak as one who has had some hookups and had some experiences on Tinder and all the rest.

For the most part, these experiences often leave us feeling a bit shallow and deflated.

The common consensus is, there’s really no comparison between sex and intimacy with someone you love, and a random fling. That doesn’t mean anything.

I recorded a video recently talking about comparing hookup culture and comparing flings to eating. Drunk and eat at McDonald’s at 3 am, having a couple of big macs. As compared to sex with someone you love being more like a five-course meal with candlelight and this incredible experience.

Sometimes people need both of those experiences to have some perspective.

You can take it from me and from a lot of people who’ve participated in a hookup culture that it isn’t often all it’s cracked up to be.

It can sometimes do more harm than good to people. And if your motives or intentions are to engage in hookup culture to cure retroactive jealousy, that is just jumping into bed with someone new, but it’s not going to solve your problem.

Overcoming retroactive jealousy requires a holistic, multifaceted approach and requires some deeper investigation.

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.