20 Questions to Ask a Guy to Get Closer post image

20 Questions to Ask a Guy to Get Closer

In this age of endless connection, we are more disconnected than ever and most relationships don’t go very far beyond the surface. Maybe it’s because we hold ourselves back or maybe it’s because we no longer have the tools to genuinely connect, like face-to-face and via conversation.

In order to build the foundation for a relationship, you need to create a meaningful connection, and this comes when you truly connect with who the other person is.

A little while back, I discovered this site called Thought Questions and I started keeping a list of some of my favorites. When my husband and I were still dating, I pulled up the list one night and suggested we play the “questions game.” We also mixed it up by seeing if we could guess what the other person would answer. It was a lot of fun, but also a very profound experience and we ended up learning so much about each other (and about ourselves!), which brought us even closer. To this day we make an effort to spend time asking each other deep, meaningful questions that go beyond ‘how was your day?’ And every time we do this, we discover new and interesting things about each other.

In his book “The Seven principles of Making a Marriage Work,” famed relationship researcher John Gottman (the dude who can predict whether a couple will get divorced with something like 95% accuracy after watching them interact for only a few minutes) cites “enhancing your love maps” as the first principle. A love map is essentially knowing all relevant information about your partner’s life, from small things like the name of their first pet to big things like significant experiences that shaped who they are. He explains that couples who have detailed love maps of each other’s worlds are much more equipped to cope with stressful events and overcome conflict.

The point is, knowledge is powerful and asking the right questions can unlock the gates for a meaningful connection and deep understanding of one another. It doesn’t matter what stage of a relationship you’re in, it could be the first date or your 10th year of marriage, people are deep and complex and always evolving so there is always something new to learn.

To help you tap into the power of knowing, here is a list of my favorite bonding questions to ask your guy in order to get even closer and more connected.

1. What’s something you’re glad you’ll never have to do again?

This questions can be very telling. Usually the experiences we never want to do again were the hardest, but also the most transformative, the ones that helped shape who we are. Usually the worst things we go through in life are the things that make us realize how strong we are.

2. What’s one thing you always procrastinate on?

This is a good question to see how grounded and efficient someone is. There’s always a reason why we procrastinate on something, but we don’t always immediately know why. People who are more floaty types will usually procrastinate on practical, day-to-day tasks while people who are more Type-A and goal-oriented will have a hard time with feeling-tasks.

3. What would you do with your life if you were suddenly awarded a billion dollars?

questions-to-ask-a-guyWe all pretty much work to live and while you might enjoy your job very much, it might not be the thing you would choose to do if you didn’t have any bills to pay. This question is telling because it shows what someone values in life and what their deepest desires are. Do they want to travel the world? Dedicate their life to charity? Teach underprivileged kids? (These are actually some of the responses I’ve gotten to this question on dates!)

4. What should a healthy relationship provide for the people in it?

Everyone has different needs in a relationship, they have things they are able to give and things they want to receive. People usually give love in the way they most feel loved, but not everyone experiences love in the same way. When you and your partner complement each other in terms of what you each want to give and get, having a loving, healthy relationship will be pretty seamless. If you have different needs, then you might need to work a little harder to each person is satisfied. Either way, this is a great question to gain an understanding of how he views relationships.

MORE: 11 Signs He Is In Love With You

5. Do you believe everything happens for a reason, or do we just find reasons after things happen?

Most people are divided into two categories, the ones that thing everything is destiny and the ones that think life is a series of random occurrences. This thought provoking question will give you insight into where he stands and is sure to rouse some very interesting conversation.

6. Is there anything you consider absolutely unforgivable?

Someone’s answer to this question will probably depend on their life experiences, for instance, if they’ve been cheated on and now consider that unforgivable. Some people can forgive anything, others are pretty tough and may have a low threshold for certain behaviors.

7. If you woke up tomorrow with no fear, what would you do first?

Now wouldn’t that be a fun thing to wake up to! Use this fun question to figure out what he really wants to do in life, and what’s holding him back from getting there.

8. In your life, what has been the biggest blessing in disguise?

We’ve all had experiences that felt like the worst possible thing that could happen at the time and ended up being one of the best things to ever happen, and it can be fun to look back and see that a lot of the time, things do work out for the best.


9. If you could pick one year of your life to do-over, which would it be and why?

People can interpret this question in different ways. Some might want to re-live a year that was really fun and amazing and others might want a re-do of a year where they made significant mistakes. Either way, it’s fun to think about.

10. What is one behavior that you never tolerate?

Everyone has their personality pet peeves, guys in particular can get very turned off (even if they’re out with a supermodel) but certain behaviors that they find completely unattractive. When you ask him this question, you’ll learn his deal breakers (hopefully) before you commit any of them!

11. Does spending time with other people energize you or drain you?

This question will tell you if he’s an introvert or extrovert. A lot of people think it’s easy to distinguish between the two but it’s not. People assume extroverts are fun and friendly and chatty while introverts are shy, withdrawn, and quiet. This mistake is the reason why I thought I was an extrovert my entire life when really, I’m an outgoing introvert! Extroverts usually feel energized by being around people while introverts need time alone in order to re-charge.

12. If you could write a note to your younger self, what would you say in only three words?

This question is both sad and sweet, because don’t we all wish we could impart some wisdom onto our younger selves? It also has the potential to talk a bit about your childhoods, which is a really significant way to get to know someone since so much of who we are was shaped in our early years.

13. What is the one thing that makes you feel alive?

We all have something. Men in particular need to feel like they are achieving their “mission” in life. Every man has one, but not all of them are actively working to achieve it. His mission is usually the closest thing to his heart, the thing that makes him feel alive. This question will give you insight into what his mission is, which will tell you a lot about who he really is.

14. What would your perfect day look like?

It doesn’t have to be a special day (although he might interpret this question that way, like my husband who answered, “our wedding day”), it can be his perfect ordinary day. What time he wakes up, what he does, who he sees, what he accomplishes. This will show you what makes him feel good and on top of the world. We all have those days where everything clicks and everything feels right and they’re the best! This is a great way to find out what his looks like.

15. Is social media bringing us closer or making everyone more isolated and alone?

This is just a great conversation starter because you can easily argue both sides. It’s not as personal as the others, but it’s a fun thing to talk about and a great ice breaker if you’re in the early dating phases.

… (continued – Click to keep reading 20 Questions to Ask a Guy to Get Closer)

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