12/06/2025
"8 Deep Questions to Ask a Guy You Like — Without Sounding Desperate or Thirsty"
“Because wisdom listens. Flirting can wait.”
✨ 1. “What shaped your view of love growing up?”
This doesn’t sound flirty. It’s just real.
It opens the door to his past, his beliefs, and his emotional upbringing.
Does he have unresolved wounds? Does he even think about these things?
🧠 2. “What’s something you’re still trying to unlearn about relationships?”
Now this one sounds introspective, not romantic.
And it’s a great way to see his level of emotional maturity without making it about you.
Bonus: You’ll quickly see if he’s defensive, playful, or honest.
🪞 3. “What do you think most people misunderstand about you?”
Boom. This question touches both vulnerability and identity — without sounding like a “Do you like me?” trap.
Quietly observe: Does he have self-awareness? Does he feel safe being known?
🙏🏽 4. “Who calls you out when you’re slipping spiritually or emotionally?”
Girl, if a man has no accountability, he’s a walking red flag with cologne.
This question sounds innocent, but it checks for discipleship, correction, and character.
🔥 5. “When was the last time you felt really convicted about something?”
You’re not asking this to play Holy Spirit, but to understand his capacity for repentance.
No need to react too much—just take mental notes.
🎯 6. “Do you believe men and women can truly be friends without ulterior motives?”
Whew. Now this one is spicy — but it’s disguised as a conversation starter.
His answer will tell you what he really thinks about boundaries, temptation, and self-control.
💼 7. “What’s something you’re building that you don’t want to fail at?”
This taps into purpose and drive — and shows what he’s committed to long-term.
If his answers are shallow, the man might just be living for the moment.
❤️🩹 8. “What’s something you’ve healed from that people don’t even know about?”
This hits deep but softly.
It’s not “trauma-digging,” but it’s an invite to be seen — without forcing it.
📖 Takeaway:
You don’t need to flirt to know if he’s worth your “yes.”
You just need to listen with discernment, not desperation.
As Proverbs 20:5 says, “The purposes of a person’s heart are deep waters, but one who has insight draws them out.”
Let your questions be like a well — not a spotlight.
Draw him out. Don’t try to define him too quickly.
✍🏾 Okoye Precious | Your Relationship and Godly Living Coach.
