Olalekan Adebumiti
You already know how to turn heads.
You know the power of a red lip, the right perfume, and that look you give across a crowded room.
You know how to be desired.
Until you are bored with just being desired!
You are tired of men who stare at your body but glaze over when you talk about your passions.
You are tired of the same three questions: “What do you do?”, “Where are you from?”, and “Do you come here often?”
You want a man who falls in love with the way you think.
You want to be the woman who lingers in his mind long after you have left the table.
To do that, you have to stop answering his boring questions and start asking dangerous ones.
You have to invite him into the maze of your mind and see if he can find his way out.
Here are 10 questions to ask when you want to bypass the small talk and touch his soul.
1. “What is the one thing you have failed at that you are most proud of?”
Start with a curveball like this one.
Most women ask about success. They want to see the trophies.
By asking about failure, you are telling him two things: First, you aren’t afraid of imperfection. Second, you value resilience over luck.
Watch his eyes light up. He rarely gets to brag about the battles he lost but survived.
This makes you safe, and you can thank me for it when it works.
2. “If you could witness any event in history, just as an observer, where would you go?”
This is a values test, not a history quiz.
Does he want to see a gladiator fight? He craves adrenaline.
Does he want to see the moon landing? It means he loves progress.
Does he want to see Woodstock? He’s a free spirit.
This question unlocks his imagination and makes him associate you with his biggest dreams.
Don’t be lost yet… The biggest dream here isn’t your fantasy.
3. “What is a controversially held opinion you have that you can actually defend?”
We have a playful one here that doubles as a challenge.
You are asking him to be bold. You are telling him, “I can handle your sharp edges.”
Whether he thinks pineapple belongs on pizza or has a theory about politics, this question creates instant friction, and the good kind, for that matter.
It turns a polite date into a debate. Passion lives in the debate, this debate.
4. “When was the last time you cried?”
Use this one carefully. It is a scalpel.
Most men are taught to hide their emotions.
By asking this casually, perhaps over a glass of wine, you are stripping away that toxic armour.
If he answers honestly, he has just trusted you with his vulnerability.
That is the glue of intimacy, and you’re free to get stuck in the thrill of it from here on.
5. “What is the best piece of advice you’ve ever received, but ignored?”
We all have that one warning we didn’t listen to.
This question makes him laugh at his younger, stupider self.
It allows you both to bond over the mistakes of youth without the heaviness of regret.
It shows you have a sense of humour about life’s messiness.
The best social tactician that ever lived, take your crown!
6. “If you had to teach a class on one thing tomorrow, what would it be?”
This one here makes him the expert, as men love to feel competent.
Maybe he’s a secret expert on 1980s synthesisers, or perhaps he knows everything about cooking the perfect steak.
You are giving him the stage to shine, and you get to watch him speak with authority and passion.
Passion is contagious, and you are the conduit, dear.
7. “Who in your life do you most want to impress?”
Is it his father? His boss? His future self?
Knowing who he performs for tells you everything about his drive and his insecurities.
It shows you are interested in the why of his life, not just the what.
8. “What is the one luxury you would never give up, even if you were broke?”
Is it good coffee? High-speed internet? A gym membership?
This is a fun, light-hearted question that reveals his non-negotiables.
It tells you about his lifestyle without asking “how much money do you make?”
It paints a picture of what a Sunday morning with him would look like.
You have given the empty canvas, let his imagination wander!
9. “What is a compliment you hear often that you actually hate?”
I expect this to catch him off guard, as we assume all compliments are good.
Maybe he hates being called “nice” because he thinks it means “boring.”
Maybe he hates being called “strong” because he’s tired of carrying everything.
This question shows you see the complexity in him that others miss.
You are the mystery solver, let’s pay you the homage.
10. “If we dropped everything and drove to the airport right now, where would we go?”
Notice the “we.”
This is the closer. It’s a fantasy question.
It puts the two of you in a scenario of adventure and spontaneity.
It plants a seed in his brain: You and me. Together. Escaping.
Even if you never leave the bar, for a moment, you have already travelled the world together.
The “Deep Breath” Moment
You see?
You don’t need to play dumb to make a man feel smart.
You don’t need to be quiet to let him lead.
The most attractive thing you can wear is your curiosity.
When you ask questions like these, you aren’t just making conversation. You are building a world.
You are showing him that you are not just another pretty face to look at. You are a fascinating mystery to be solved.
And darling, the right man will never want to stop solving you.
Clap for yourself.
