Dating and Relationship Advice

We all know that guys in general aren’t so emotional. It takes time to make him open up to you. But what happens if you don’t know what personal questions to ask a guy? Because you don’t want to ruin the connection by asking the wrong questions.

It’s not that complicated but it’s also important to understand that not all guys are ready to open up — especially when the relationship is still young. If that’s the case, you need to be more patient and respect his decision.

Top 10 Personal Questions to Ask a Guy to Open Him Up

Here are 10 personal questions to get him to open up to you:

1. “What do you learn from your past relationships?”

Instead of asking why he broke up with his ex, ask about the lesson he learned. Many guys don’t process their emotions after a breakup and if you bring up this question, it’ll give him a chance to do just that.

2. “What are the things that bring you joy?”

This should be on the top of your personal questions list because asking this will make him feel like you care about his happiness outside the relationship.

3. “How was your childhood? Did you get the love you needed from your parents?”

Childhood trauma is real and it can impact your relationship in so many ways. Asking this question will surely strengthen the bond.

4. “Do you like your job?”

This question might sound simple but it’ll lead to some deep conversations. If he doesn’t like his job, you can ask follow-up personal questions such as, “What’s your dream job? any creative ideas you’d love to try?”

5. “What’s your lowest moment in life so far?”

Not many men want to share their lows so if you can get him open up about it then you’ll have his trust. To get it started, it’s easier if you start by sharing your experience first. and then ask, “What about you?”

6. “Do you see yourself settling down with someone in the future?”

This question is a great way to see if you both want to be together long-term. It’s also heartwarming for guys to know that you’re also interested in hearing their perspectives on marriage.

7. “What’s your ideal relationship should look like?”

Does he think compatibility matters? What are the things that he’d like to try with his future partner? Is traveling together on the list too? By asking thesWhat’s

8. “What are your current goals (money, career, and life in general)?”

These are my favorite personal questions to ask a guy. Most men are career-driven so this will make his eyes light up. It’s also a fun way to get to know more about his personality.

9. “Are you happy where you’re right now?”

This question is more like you want to check up on him to see how is he feeling overall. Guys won’t open up just because you ask them “How are you?” so this question will help them get started in being vulnerable to you.

10. “How do you usually express your feelings? How often do you do it?” 

My therapist recommended people ask these questions to deepen relationships. Knowing how he expresses his emotions is crucial. Without knowing his way of coping with problems, it’ll be harder to navigate the relationship. 

The Importance of the Right Timing

When’s the right time to ask these personal questions? Is one month too early or should you wait for another month?

On Iris Dating, for example, you need to be as engaging as possible once you find someone with a mutual attraction. So as long as you’re confident that he wants the same thing as you do, then it’s time to ask some personal questions.

Many people wait for months to do it because they don’t know how to get a guy to open up. But it doesn’t have to be that way. Fear of rejection doesn’t have to hold you back because the earlier, the better.


Those are the top personal questions to get you started on how to get a guy to open up. The thing is, many people don’t think it’s important enough to learn this skill.

But on a dating App like Iris Dating, mutual physical attraction alone isn’t enough to help you move the relationship outside the App. You still need to put effort into creating a strong emotional bond.

At the end of the day, a perfect match doesn’t come every day so if you have one right now, you might as well do your best to make it work. 

Related: 3 Ways to Overcome Shyness in Bed, According to Science

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