Olalekan Adebumiti
He drops the grenade right in the middle of a routine phone call.
You are wandering around your kitchen, phone pressed to your ear, laughing about something trivial that happened at work. The conversation is warm. It flows. Then, out of nowhere, the line goes quiet, and he asks it.
“So, how many guys have you actually been with?”
Or perhaps: “Why did you and your ex break up, exactly?”
He asks it casually. His tone is light. He acts like he is just making conversation, like he is asking what you want for dinner. But your stomach drops. Your heart skips a beat. You know this isn’t a casual question. You know this is a trap.
If you answer literally with the raw data, the numbers, and the messy details, you risk triggering a meltdown. If you lie, you risk breaking trust. You feel cornered.
The mistake most women make is answering the words instead of the intention.
Men rarely ask about the past to get data. They ask to get reassurance. They are looking for safety, but they are using the language of interrogation. They are asking specific questions to soothe specific, primal fears.
If you want to survive this conversation without an argument, you need to learn to speak his language. You need to hear the question behind the question.
Here is your translation guide to the 6 most dangerous questions men ask, and what they are actually trying to find out.
1. He Asks: “How many men have you slept with?”
He Means: “Are you impulsive, or are you selective?”
This is the most dreaded question in modern dating. We call it “The Number.”
When he asks this, he isn’t actually interested in the arithmetic. He doesn’t want to visualise a queue of men. He is trying to perform a risk assessment.
In the male mind, a high number often signals impulsivity. It signals a lack of attachment. He worries that if you gave yourself away easily to many others, his “acquisition” of your heart isn’t as valuable.
He fears that he is just another number in a sequence that will continue long after he is gone.
He is asking: “Did you choose me, or is it just my turn?”
The Strategy: Do not give him a specific number if you can avoid it. A specific number gives him a specific visual. Instead, answer the value system.
Instead, tell him: “I don’t keep a scorecard, but I can tell you that I haven’t always made the best choices in my past. I used to look for validation in the wrong places. But I am different now. I am selective. And I selected you.”
This answers the fear (that you are impulsive) without feeding the monster (the mental image of other men).
2. He Asks: “Why did you and your last ex break up?”
He Means: “Are you the drama?”
He isn’t asking for the story of your heartbreak. He doesn’t want to hear about how toxic your ex was, or how much you cried.
He is looking for accountability.
He wants to know if you are the common denominator in your failed relationships.
- If you say, “My ex was crazy, and the guy before him was a narcissist, and the guy before him was a psycho,” he hears: “I take zero responsibility for my life. I am the problem.”
- He is terrified that in six months, he will be the “crazy ex” you are complaining about to the next guy.
He is asking: “Are you going to ruin my life as you ruined theirs?”
The Strategy:
Be brief, and own your part in it.
Say: “We just weren’t compatible. He needed someone more traditional, and I needed someone more ambitious. We grew apart. I learned a lot about what I don’t want, which is why I appreciate you so much.”
This shows maturity. It shows you can reflect on the past without being bitter. A man feels safe with a woman who owns her history; he feels unsafe with a woman who plays the victim.
3. He Asks: “Was he good in bed?”
He Means: “Am I enough?”
This is a masochistic question. He knows he shouldn’t ask it. He knows the answer might destroy him. But his ego is driving the car, and his ego needs to know where he ranks on the scoreboard.
He is terrified of the “Alpha Widow” scenario—the fear that you had mind-blowing, earth-shattering passion with a “Bad Boy” in your past, and now you have settled for him because he is “safe” and “reliable.”
He doesn’t want to be the “Safe Guy.” He wants to be the “Greatest of All Time.”
The Strategy:
Never, ever lie and say your ex was terrible if he wasn’t. But never, ever give details about how good he was.
Pivot to the connection.
Say: “He was experienced, sure. But we had zero connection. It felt like a performance. With you, it’s intense because I actually love you. The chemistry we have is completely different.”
You are telling him that he wins the category that matters: Intimacy.
4. He Asks: “Did you do that style with him?”
He Means: “Did you give him the ‘fun’ version of you?”
This is a dark one.
He asks if you did certain adventurous things with your ex. If you say “yes,” he gets upset. Why? Because if you did it with your ex but you haven’t done it with him, he feels short-changed.
He feels like the ex got the uninhibited, wild, “fun” girl, and he is getting the “wife material” version who has boundaries and rules. He feels like he is paying full price for a service others got for free (a crude analogy, but an accurate description of the feeling).
He is asking: “Why was he worth the effort, but I am not?”
The Strategy: Context is everything. If you did things in the past you don’t do now, explain the why—and make the “why” about your growth, not his lack of appeal.
Say: “I did try that, and honestly, I didn’t enjoy it. I was doing it to please him because I was insecure. I don’t do it now because I respect myself more, not because I’m boring. I want to do things that we both enjoy.”
5. He Asks: “Do you still talk to him?”
He Means: “Is the door actually shut?”
He isn’t asking about your social habits. He is asking about Territory.
Men are territorial creatures. If you are still texting an ex, meeting him for coffee, or liking his photos, your man does not see “friendship.” He sees an “Orbiter.”
He sees a man who is waiting on the sidelines for your relationship to fail so he can swoop back in. And he wonders why you are keeping the door unlocked.
He is asking: “Are you keeping a backup plan because you aren’t sure about me?”
The Strategy:
If the answer is no, say it clearly. “No. That chapter is closed.”
If the answer is yes (perhaps you share a dog, or a friend group), you need to establish extreme boundaries.
Say: “We speak occasionally about logistics, but he has no access to my inner life. You are the one I talk to. You are the one I come home to. There is no threat there.”
6. He Asks: “What was he like?”
He Means: “What is your ‘Type’?”
He wants to know the physical and personality profile of the men you desire.
If he is a quiet, intellectual accountant, and you tell him your ex was a loud, muscular firefighter, he is going to panic. He will immediately feel like he is not your “type.”
He will worry that you are forcing yourself to be with him, but you will eventually get bored and run back to the firefighter type.
He is asking: “Am I an anomaly that you will eventually correct?”
The Strategy: Focus on the upgrade.
Say: “He was very chaotic. I used to think I liked that, but it was exhausting. I realised I don’t want chaos; I want stability and intelligence. That’s why I’m so attracted to you. You are the upgrade.”
Make him feel like the evolution of your taste, not a deviation from it.
The Honest Deflection
You might read this and think, “Why do I have to manage his ego? Why can’t I just tell the truth?”
You can. You can tell him the raw, unvarnished truth. You can tell him you slept with 50 men and your ex was a god in bed. That is your right.
But you cannot control how that information lands.
Radical honesty is overrated in romance. Radical empathy is better.
When he asks these questions, he is handing you a loaded gun and asking you to check if the safety is on. He is vulnerable. He is scared. He is asking, in a thousand different ways, “Am I special to you?”
Your job is not to give him a spreadsheet of your history. Your job is to answer the hidden question.
The answer he needs is always the same:
“The past taught me what I didn’t want, so that I could recognise you when you arrived.”
