Josh Sway is an American dating coach, and author of the e-book Sway Seduction: Master Online Dating.

On his website you’ll find a wide range of articles on topics ranging from sex, to online dating, to weightlifting, and much more. After getting to know Josh a bit via email, I became curious about his take on retroactive jealousy. It turns out that even dating coaches struggle with RJ from time to time…

Below you’ll find my interview with Josh in which we discuss retroactive jealousy, self-improvement, and general relationship advice. I hope you’ll enjoy.

Me: Have you ever been jealous of a girlfriend’s past? If so, how did you deal with it?

Josh Sway: I most definitely have. I have learned my lesson and now try to go out of my way to avoid learning about women I dates’ past. Nothing good will really come out of it. With that said, I still had situations where I learned things I did not like.

My advice is probably the opposite of what most experts would say, and it is to simply try my best not to think about it. I stopped bringing it up, and anytime any conversation about the past (especially sexual things) came up I would very openly say I don’t want to talk about it.

Another thing I have found has helped me is to be more open with sexual experimentation and in particular being more dominant in the bedroom. Usually, jealousy factors related to a girlfriend’s past involve feeling inadequate or not as physically attractive as other men from her past. Being in charge in the bedroom and your girlfriend enjoying it is a good way to help alleviate those concerns.   

What is the number one tip you have for guys who want to improve their relationships with women?

In terms of being in a relationship, I find one of the most important things is for there to be a balance of power. One person can’t be driving everything in the relationship as this is simply unsustainable. Be open about what is important to you and at the same time, don’t dominate the entire relationship.

Many of my readers are in long-term relationships that have been badly damaged by retroactive jealousy. What advice would you give them if they want to rebuild their relationship, and be a better boyfriend or husband?

The best advice I can give in this situation is two fold. For the future, be open about your concerns regarding the future but at the same time pick your battles. In terms of overcoming the past, I have done my best by simply avoiding any conversation about the topic and trying my best to just not think about it. Some stones are best left unturned. Remember, at the end of the day, she potentially didn’t even know you when the events that bother you happened.

A lot of my readers set out to work on their insecurity after they read my guidebook. What advice would you give them if they want to improve their self-esteem? How do you build confidence?

I build my confidence by focusing on the present and the future as opposed to the past and by going out there and being a “doer” as cheesy as it sounds. When it comes to my mental mindset, I look at how far I have come and focus on that trajectory as opposed to harping over any past failures.

However, the truth is, my confidence and self-esteem have always been tied hand to hand with my accomplishments and the friends, relationships, and social connections I have built. I have never had much success looking at myself in the mirror telling myself I am a high value individual, giving myself pep-talks, seeing a therapist, or being introspective.

I have had the biggest boosts in self esteem by going out there and making tangible changes in my life, such as going to the gym, going out and meeting women, working on changing the nature of my relationships if I wasn’t happy about them, pursuing changes in my career, making friends, and more. And, I found forcing myself to do these things even if I didn’t feel like it has had by far the biggest positive effect on my self-esteem and confidence.


Click here to visit Josh’s website.

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.