So he cheated on his ex: Questions you have to ask him and yourself before you commit

You’re dating this guy and everything is going well, in fact, things look promising. Then that awkward moment comes: you talk about your past, and he talks about his. Unfortunately, you find out that he cheated in one (or more) of his previous relationships. Then that paranoia sets in, and you start wondering if he’s gonna cheat on you too.

And I don’t blame you, but hear me out.

I wouldn’t say that the old saying “once a cheater, always a cheater” is true, but as a precaution we have to pay attention to see who the cheater really is, why they cheated and how they reacted after the whole thing to accurately judge them. Let’s break this into pieces so we can analyze your situation better:

First of all, let’s get rid of the serial cheaters, because they are the least complex when it comes to judging whether you should give the relationship a chance or not. If the guy has cheated on every single girlfriend he’s had (and I’m assuming he didn’t have just one girlfriend before you, of course), run. Most likely, these types won’t be completely honest with their stories (nor in general), but if his list of bitter cheated exes is big, he’s not the one for you.

Now, let’s say he LOOKS decent and he doesn’t have 3, 4, or maybe 20 exes whom he has cheated on. Let’s proceed to the next screening tests:

Ask about what happened:

Was it an impulsive behavior?
The types that say that it was the heat of the moment or blame the booze are completely unreliable. Unless he was a teenager when he did it and he now deeply regrets his condemnable acts, I’d advise you to move on. The great majority of cheaters have poor self-control. They are short-sighted and will give up on long term goals for instant gratification. It’s one of the major symptoms. Yes, I called it a symptom.

Was it vengeance?
If yes, then NOPE. You do not want someone who will cheat on you because you guys had a fight. Just. Say. No.

Did the relationship die out?
Was it a long-term relationship? Did he work hard on it? Why didn’t he break up instead of cheat?
Look for signs of honest commitment during his answer.

Did his (now ex) partner find out through other sources, or did he tell the truth and admit his mistake?
Was he upfront about it right after it happened or did he try to hide it?
If he had an affair and pretended that everything was fine, looked at her face and kissed her like he was still devoted to her, I wouldn’t call him a good person. If he acted like the perfect husband/boyfriend until being caught red-handed, he’s no bueno.

Although cheating is NEVER the answer, some people stray and, afterwards, become distant from their partner because they don’t know how to get out of the situation: for example, a sexless marriage that is only being sustained for the sake of the kids/family. Again – let me reiterate this – cheating is never the answer, but the person in this example is less likely to do the same to you than a sociopathic fella who cheated on his wife for 5 years straight, while pretending to love her more than anything in the whole world. This case is the toughest to weigh in about, because while some people do have weird relationship patterns, the reality is that most people don’t like living with a partner who they can’t even look in the eye. Living with a guilty conscience is never pleasant, and most people wouldn’t want to repeat the experience.

And regarding blaming his partner, or playing the victim card, take those as red flags. It doesn’t matter what happened, there is no free pass when it comes to cheating. No excuses. If he doesn’t truly regret his deplorable actions (and yes, that includes cheating on “Satan’s spawn”) he is not boyfriend/husband material.

I hope this helps if you’re having a hard time trying to decide whether or not to invest in a partner with a dark past. Remember to analyze the situation with your brain before giving him your heart.


For questions and appointments/coaching sessions:



  1. These are all important signs to look out for. But what if the person does not want to talk about his or her past relationships? Some counsellors say we should respect that and not talk about it unless the person wants to.


    • Hi! So, I think that at least the reason for not talking about it should be discussed. Of course, some people went through abuse or other traumatic experiences and they don’t want to talk about it. That’s completely understandable (although that should be the case of talking about it in therapy) . But let’s say the person had 4 serious relationships before meeting you. Why wouldn’t they be able to talk about any of them? That’s a bit awkward, isn’t it? Talking about it at least on a superficial level is important. 🙂


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