Pete Uglow | Should We Date Someone With a History of Infidelity?

Once a cheater always a cheater. I’ve previously written on the myths surrounding infidelity multiple times, as have other relationship experts, yet the saying just won’t seem to budge. It is an understandably sticky sentiment. A bit catchy and nicely alliterative, it preys on the fears and insecurities that come along with discovering a history of infidelity. 

Realizing that our partner has cheated on someone, or many people, in their past can certainly conjure up the popular myth. It is only human to worry that we will turn out to be the latest victim in a string of infidelities, but that doesn’t mean our worry will come to fruition. 

If there are two truths I have learned after years of experience counseling couples affected by infidelity it’s that everyone has the capacity for change and that the catalysts of unfaithful behavior are likely to reside with work and effort. So, with that in mind, why wouldn’t we try to extend to our partner the benefit of the doubt?

Now, that’s not to say we should bury the questions or fears we have surrounding their past behavior. If we’re worried about whether we can trust our partner again, it’s essential to have a conversation where they can tell you their story. After all, infidelity can be caused by a variety of factors, such as personal insecurities, fear of commitment, poor management of dissatisfaction in relationships, or just not being ready for a serious, monogamous relationship. Of course, those reasons don’t justify infidelity, but they could be remedied with work, time, and maturity.

When having these discussions with our partner, it’s important that we refrain from judgement. We may want to point fingers or feel inclined to resort to shame, but making them feel like we’re interrogating them will only make them more defensive. Reserving judgement until they tell their story is important to finding out the whole truth. If the conversation becomes too upsetting for us or our partner, it can be helpful to take a step back and revisit the topic at another time. 

We also shouldn’t jump to conclusions if our partner is immediately defensive or reluctant to share details of their previous infidelity. Shame and guilt are powerful emotions and can make it difficult for us to talk about the experiences that we regret. In these instances, we can use our own emotions towards the situation to explain why we want to hear their side of the story. More often than not, our partners understand that they would feel the same way if the roles were reversed. 

Though these conversations are surely challenging, they can give us the clarity we need to decide whether or not a relationship is still worth pursuing. The answers our partner gives to the questions we ask, as well as their current attitude and feelings toward their previous infidelities can tell us a lot about how they might behave moving forward. 

Originally posted on