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I have been dating a guy for almost three months now, and things are going great. We have a great emotional connection and physical chemistry. We’ve had a lot of deep and meaningful conversations about our pasts, as well as what we are hoping for in the future. But one thing seems to always creep in the back of my mind. In our honest conversations, he has disclosed that, in his previous long-term relationship of five years, he had cheated multiple times early on. He says they worked through it to a degree and had been faithful the last two years of the relationship. Inevitably, he thinks there were still unresolved issues from that experience which led to their inevitable breakup. He admits that he had a very immature view on relationships at the time, and that he has learned a lot about himself and how to be a better partner moving forward. He’s given me no indication that he has any intention of repeating that behavior again in our blossoming relationship but there’s still something in the back of my head that says, “Once a cheater, always a cheater.” Am I being foolish for wanting to trust him?
Hello Cheater Changer,
The back of your mind sounds an awful lot like the back of my mind. I grew up in a household where fidelity was an issue. It made me super cautious about falling in love with cheaters. If you’re a long-time reader of the column, you may recall I broke up with a young man in January when his other girlfriend made herself known on my Instagram. This young man constantly spoke about his father’s promiscuous ways and how his mother had unfairly accused him of being like his father his entire life. He brought up this topic so often that, in the back of my mind, I felt like there was more to it. But I decided to continue dating him until I had something more concrete to hold onto. He was cute and fun to be around, and it was a nice break from being single during the cold winter months. But our physical connection was weak, and he had plans to move several hours away to a city I didn’t care to visit. In other words, I didn’t feel like I was risking much by letting things play out. I wasn’t super invested in a long-term future with this fella. When I found out he was cheating, I called him up, broke up with him and moved on with my life.
At the same time, there’s a guy I was into for almost 10 years. He told me when we first met he was the cheating type. We never officially dated, but hooked up casually — whether he was in a relationship with someone else, or not. He never changed over all those years. Even when he expressed interest in settling down, it just didn’t seem like he could find a person to be satisfied with and even began to think of himself as bad at love. When opportunities presented themselves to be with this guy, despite or because of how into him I was, I could never really get myself to fully commit to giving us a chance. On some fundamental level I just couldn’t trust him, and I couldn’t deal with the massive amounts of heartbreak I’d have to face if he cheated on me.
So, what you have to decide is how much you have at stake? Depending on how invested you are in this man and your relationship, you might later learn he’s still up to his cheating ways and find it easy to walk away. But if you’re super deep into this guy, then you might find out he’s cheating and decide to give him another chance… And another chance… And another chance. You might find yourself unable to move on from a bad situation. If that’s you, then I recommend you listen to your gut now. Break it off while you still can.
But if you’re the type who has no problem letting go and seeing what better thing might be on the horizon, then I say take the risk and find out if this leopard has changed his spots or not. If it doesn’t work out, you’ll be single and ready to mingle by spring.
Hey readers, we have one more set of organic lube to give away to whoever sends me the best story or question about a lover who… slipped away. Shoot me an email at email@example.com