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[Dear Madison] I Think My Boyfriend is Cheating on Me

Dear Madison,

I have a feeling my boyfriend is cheating on me. Last week, he met up with a close girl friend from NUS for her birthday. They have known each other since secondary school, and I always get the feeling like he is into her.

I found out through a friend that he bought her a Daniel Wellington watch ($200-300), but when I confronted him, he assured me that a few other friends split the cost with him. I asked him who these friends were, but he got very defensive, and started questioning how much I trust him instead.

Another incident last week left me with doubts until today. He told me that he would be spending the night till late in school to prepare for his presentation in Week 3. But when I was scrolling through the girl’s IG story on that day, she was in her room, and I heard my boyfriend’s voice. My friends thought that it wasn’t his voice, but I know for sure that it is his voice that was in the story.

Am I just being paranoid? Or should I go with my gut and break up with him?




Dear Conflicted,

I understand these feelings of paranoia you are experiencing. Many of us have been in relationships and at times felt a tingle of doubt as to whether our partners are faithful to us.

What I’ve realized, though, from the experiences of others and my own as well, is that these feelings often point to deeper, less-obvious issues that have little to do with loyalty. I’m guessing deep down you knew that too – otherwise you wouldn’t be asking me, someone even less likely to know the truth than you, whether you’re being paranoid.

Something else about your relationship is bothering you and I hope I can help you find what it is.


One of the hardest things to achieve in a romantic relationship is the habit of open and honest communication: day-to-day conversations where both parties feel comfortable enough to share intimate feelings and details of their lives with each other.

This crucial habit takes time, effort, and a lot of trust. And so it doesn't help that we tend to instead hold ourselves back from opening up, even without realizing it. People don’t intuitively open up to strangers or new friends about their deepest feelings. The same goes with our partners. Sometimes, it’s our pride that stops us. But I believe most of the time, and in your case, it’s fear.

The fear of losing the person we love. The fear of hurting them or ourselves. Opening up leaves us vulnerable.

We let our fears get the better of us and do things we don’t actually want to do. We leave them on read, hide things to avoid arguments, interrogate them over the smallest of things… when all we really want is assurance that things are okay.

But fear can help us if we let it. If we unpack that fear, it allows us to tackle the root of the problem. For instance:

Your letter reminds me of a memory from a previous relationship. My boyfriend, fighting back tears, once said to me in almost a whisper, “Why would I share anything with you? You’re never on my side.” His eyes were furious and hurt, his words soft, yet they echoed in my head. It struck me to my core.

I pride myself on being objective and a problem-solver. I wanted to and believed I could help my boyfriend fix anything that bothered him, but never considered what he needed most. Sure, sometimes my proposed solutions were helpful. But more often than not, what he needed most was to feel heard, seen, and assured that I had his back. To really listen. What was he saying, and what was he really saying?

When he said: “I’m worried I’ll screw up my presentation tomorrow”, I heard: “What should I do to make my presentation better?”. With just a little more thought, I would’ve heard: “I’m nervous and doubting myself. You know me well. Can you remind me that I’ve got this?” In trying to do what I thought was best for him, I showed him that I had not considered his feelings, not understood him, and not shown enough empathy.

My fears of him keeping things from me and his fears of opening up pointed us in the exact direction to fix what needed to be fixed. I needed to listen, and he opened up to tell me that. After that talk and a few more, our relationship improved immensely.

You mention that you confronted your boyfriend on a certain occasion, and I wonder if potentially accusatory tones may have seeped into the way you approached him, causing him to put his guard up. People want to be understood, not maligned. Even detectives use this method when trying to extract a confession: they attempt to empathize with the suspect, convincing them that their reasons for doing what they did were, although criminal, understandable. (p.s. not implying that your boyfriend is guilty!)

This lack of healthy, open communication might be a stumbling block in your relationship with your partner. The good news is that it can be worked on. Tell him about your day. Confide in him. If or when he does open up to you about his feelings, make sure you listen, and make sure he knows that you appreciate it.

The bad news is that either one of you might not want that.

Conflicted, you allude to the fact that your gut is already telling you to move on. This is a big sign that you might not really want to work this out at all, regardless of whether you think he’s cheating on you. In matters of love and life, you would do well to heed the sentiment of your heart above the reason of your mind. Take a second to ponder, under the assumption that he isn’t being unfaithful, if your partner is someone you want to continue seeing romantically. If the answer is no, then you know what to do.

If the answer is yes, I’d suggest starting with smoothing out the foundations of your relationship by displaying trust, empathy, and understanding in your actions and in everyday conversations. Share more. Listen more. Trust more. Show your desire for a healthy relationship by treating him the way he wants to be treated (see: golden rule). Not only would you be showing him how you feel, you would also be giving him a chance to reciprocate these feelings and mend the relationship with you.

Nevertheless, pay attention to the feelings of insecurity you alluded to early on. Feeling suspicious of your partner’s friends might be a symptom of jealousy, an accurate premonition that something is wrong, or maybe both.

There is no simple solution, especially because you’ll never really know the truth. Holding your partner back from his personal friendships isn’t healthy (it’s toxic, I’d argue), as is spending your Friday nights worrying about him being unfaithful. Ultimately, the best way forward is to communicate with each other. Truly communicate with each other. Not in a “I’m-telling-you-this-so-I-hope-you-get-the-hint” kind of way. The point is to give your partner the opportunity to give you assurance, and for you the opportunity to trust him.

A large part of being in a committed relationship is learning how to navigate these choppy waters together. Not all relationships last, but what endures are the experiences we gain. We become wiser, more mature, and more self-aware of what we are looking for. And that’s really the point to most things, isn’t it?

Thanks for sharing with me; you’ve really made me think. I hope I’ve helped you think through this too.




Dear Madison is for general informational and entertainment purposes only, and does not constitute or substitute medical, legal or professional advice. Always seek the advice of a professional with any questions you may have regarding a medical condition or any situation that would so require such advice.

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