When it comes to affairs of the heart, we are all beginners. Some of us, however, at least speak with authority. Introducing Shon Faye, author of The Transgender Issue (2021) and the forthcoming Love in Exile (2025), whose advice caught our eye. Contact her at DearShonVogue@gmail.com for your own chance at enlightenment.
Dear Shon,
I’ve been seeing a guy for about a month and it’s been going really well. We get on great, he treats me well, and he’s serious about building something long term. I’m really enjoying getting to know him and was just starting to get excited about the prospect of a relationship with him.
However, recently he confessed that he’d cheated on his ex. He’s been very open about it and his story matches with information that a mutual friend (of his ex’s) has told me.
He said he’s learnt from his mistakes and would never do it again. But the relationship was only two years ago, and they have been in each other’s lives since. They even slept together a few times recently. I believe that it’s over with her, but I don’t know if I should continue seeing him now that I know what he’s done in the past.
I want to believe that people shouldn’t necessarily be judged on past actions, as everyone makes mistakes, and he says the cheating took place after the relationship had pretty much broken down. But the circumstances were premeditated and callous—not a drunken one-night stand, which I feel is more forgivable.
I thought I’d finally found a good guy. He’s really keen to continue seeing me, but understands that I need time to figure things out. Should I see where it goes or cut him off now to protect myself from something that might happen in future?
At a Crossroads
Dear At a Crossroads,
You’re in turmoil because you’re afraid that if you stay with this man, he could repeat his past behavior and hurt you. But if you do not give him the benefit of the doubt, you could be missing out on a shot with a great guy. The first thing I want you to keep in mind is your own worth. This man should have to demonstrate why he is a valuable partner beyond initial chemistry. When considering what to do next, try not to let social pressure that tells you this relationship is a wonderful opportunity slipping through your fingers create a sense of panic.
It’s important to remember that most men are great in the beginning. It is very easy to be charming in the first few months of dating. Naturally, how we are treated by someone in this time is necessary to build attraction. But for a relationship, we should always look for signs of someone’s character. Character isn’t something we can make out by observing someone’s words, looks, early romantic gestures, flattery, how good they are in bed, or how cool their job will sound when we describe them to our friends. It’s evidenced by their behavior toward others, especially when they think no one (or no one significant) is watching. Disparity between someone’s words and their actions in dating should always be a cause for concern.
In this case, there are two issues at hand. Firstly, the past infidelity, and secondly, the fact that this man had sex with the same ex very recently. (I’ll return to this point shortly.) The cheating was callous and premeditated, but it was in the past. Can’t people change? Yes, I absolutely believe they can. All I can share here is what I would look for if I was seeking evidence that this guy had really changed. The fact he told you about the cheating might be a desire to be transparent, or it could simply be reputation management. On its own, it’s not good enough, nor are vague sentiments of regret. Everyone knows cheating reflects badly on unfaithful partners, and he will have known it may affect your attraction to him. Some contrition is to be expected.
What I would be looking for beyond a simple acknowledgement of making a mistake is a true understanding from this man that his behavior was premeditated and cruel. Infidelity is, above all else, cruelty. When you cheat, you make someone else’s entire life a lie. You continue to take advantage of the emotional support of having a partner on false pretenses. You are conning them out of time and energy. If discovered, you will rob them of their peace of mind and damage their ability to trust—not only you, but most likely future partners as well. Recklessness with another person’s heart is a serious matter. It’s something that should weigh on him. “The relationship was basically over anyway” is a cop out: The respectful way to end a relationship is to compassionately communicate that you are ending it. I would want to see evidence that he understands this and that he has done some inner work to learn what motivated him to behave in such a terrible way. Ideally, this should come from him, unprompted, as women often spoon-feed men what we want them to say in these situations. It can be a way to delude ourselves about the other person’s emotional intelligence. Look out for who he is, not who you want him to be.
I think you also need to consider the fact he was also hooking up with his ex very recently before meeting you. It suggests to me that there is still an emotional (and sexual) intensity to their dynamic where I would personally hope for a degree of calm and detachment. He says he cheated because the relationship was essentially over anyway and yet he’s continued to be intimate with her. Again, the only judge of whether these concerns can be quashed satisfactorily is you. Personally, I think he has a lot to work on and what you relay in your letter does not show sufficient evidence he has embarked upon that work. Maybe in person he will convince you. Either way, trust your gut and what it’s telling you.
