Deep questions to ask a guy: connect and strengthen your relationship

Wondering why you should know a few deep questions to ask a guy? Communication is the key to any successful relationship. While small talk is all well and good, there comes a point past which you need to ditch the superficial stuff. This is where deep questions to ask a guy you like come in.

In this article, we’ll explain how asking deep questions can help strengthen your connection with the person you’re dating, and offer you several different lists of deep questions to ask a guy depending on the situation and the topic.

Tips for asking deep questions

Studies show that good communication is the heart of any successful relationship¹, which is why it’s so important to make sure you’re clear and upfront with any potential dating partners right from the start. Additionally, asking each other deep questions can help you figure out if you and your date are a good match. Some tips for getting the most out of deep questions to ask a guy:

1. Be respectful: Your partner is opening up to you, and it’s important to treat that with the care it deserves.
2. Listen actively: Be sure to pay attention to what he’s saying, and respond when appropriate.
3. Choose a good time to have the conversation: These deep questions to ask a guy require time to think, so it’s best to find an occasion when neither of you are busy or stressed.
4. Consider asking via text: Asking via text gives your partner time to craft thought-out responses.
5. Let yourself be vulnerable: Going deep means being honest, so don’t be afraid to do so.

Deep personal questions to ask a guy

While you should probably not ask these on the first date, it’s always good to have a list of deep personal questions to ask a guy.

1. How do you handle differences in communication styles?
2. What was the best thing about how your parents raised you?
3. If there was a slogan for your life, what would it be?
4. What do most people overestimate or underestimate about you?
5. What is something you probably should do, but will never do?
6. Do you want kids? Why or why not?
7. If you could share a meal with any four individuals, living or dead, who would they be?
8. If you were given immortality, but there was one condition, is there anything that would stop you from accepting it? What is it?
9. What do you most look forward to about getting old?
10. What are you most grateful for?

Deep meaningful questions to ask a guy

Asking real questions helps you connect. Here are ten deep meaningful questions to ask a guy:

1. Is there anything you’ve been wanting to tell a friend, but don’t know how to?
2. If you could dedicate your life to solving one problem, what problem would you choose?
3. What’s the best advice you’ve ever gotten?
4. What do you really wish you knew when you were younger?
5. Are you trying to “break the cycle” of any family dynamics?
6. What’s your biggest fear in life, and why?
7. How do you define loyalty in friendships and relationships?
8. If you could have a conversation with your younger self, what would you say? Is there anything you’d warn them not to do, or encourage them to do?
9. What’s a philosophical question that keeps you up at night?
10. What’s a piece of technology you think the world would be better without?

Deep life questions to ask a guy

Everyone has different experiences that give them a unique perspective on the world around them. Here are ten deep life questions to ask a guy so you can find out how his life has affected his point of view.

1. Are you still friends with anyone from high school?
2. What’s something you’ve always wanted to try but haven’t yet?
3. How do you balance your time between friends, family, and personal life?
4. What’s a cultural or life experience you’d like to share with friends?
5. Is what you’re doing now what you always wanted to do growing up?
6. What’s been your biggest mistake so far in life and what did you learn from it?
7. What’s your philosophy in life?
8. What was the biggest adrenaline rush you ever felt?
9. If you could trade lives with anyone in the world, who would it be?
10. What’s your story?

It’s true that guys in the past weren’t really raised to talk about their emotions; luckily, that’s changing. Here are ten deep emotional questions to ask a guy to get you started.

1. What makes you happy?
2. Do you believe in love languages? What’s yours?
3. Do I make you feel heard and valued in our relationship?
4. What’s something you didn’t do that you regret?
5. Is there something your parents did with you that you don’t want to repeat with your own kids? What about the reverse?
6. What’s your guilty pleasure?
7. What’s something you wish I knew about you?
8. What do you think is more important for a relationship to succeed, a physical connection or an emotional one?
9. What do you think your best attribute as a boyfriend is? What about your worst one?
10. What’s your biggest regret?

Deep love questions to ask a guy

Different stages of dating require their own kinds of deep questions. This list of deep love questions to ask a guy is great for when you’ve been dating a while.

1. If you could plan a date for us anywhere in the world, where would we go and what would we do?
2. How important is maintaining individual friendships in a relationship?
3. How do you show support for your partner?
4. Do you think it’s important to get married eventually?
5. What is your opinion on sharing finances in a relationship?
6. How do you plan to deal with any conflicts I may have with your family?
7. Do you think living together before marriage is important?
8. What is your biggest fear about falling in love?
9. What’s your approach to dealing with relationship baggage?
10. What’s your stance on individual needs in relationships? What about compromise?

Deep spiritual questions to ask a guy

While belief in organized religion is on the decline, some kind of spirituality does play a role in many people’s lives. Here are ten deep spiritual questions to ask a guy:

1. Do you believe in God?
2. Do you have any spiritual practices that are very meaningful to you?
3. If you believe in God, is regularly attending religious services of some kind important to you?
4. Are there any religious or spiritual texts that have had a major impact on you?
5. What are your favorite ways to connect with your spirituality?
6. What do you do when what your faith tells you and what your conscience says are in conflict?
7. What is your stance on faith-based charity?
8. How do you feel about raising children in our religious or spiritual beliefs?
9. What role does faith play in your decision-making process?
10. Do you believe it’s important to have friends who don’t believe the same things you do?

Deep intimate questions to ask a guy

Intimacy doesn’t necessarily mean bedroom activities; it’s anything that involves a close connection with your partner. Here are ten deep intimate questions to ask a guy you’re seeing:

1. What was the first thing you noticed about me?
2. What were you afraid of as a kid? Are you still afraid of it?
3. Do you believe in soulmates?
4. What do you think is more important for a relationship to succeed, passion or hard work?
5. What are some non-sexual ways we can connect with each other?
6. Do you have any role models, couple-wise? Are there things you’d like to emulate?
7. Do you ever worry about us breaking up?
8. What is your stance on personal space in a relationship?
9. Do you think we’re communicating well enough? Are there ways we can improve?
10. What’s your opinion of scheduling regular times to ask each other deep questions?

Deep sexual questions to ask a guy

While the other kind of questions definitely have a place, this list of deep sexual questions to ask a guy is designed to make sure your experience together healthy as well as good.

1. Are there any absolute no-nos for you when it comes to sex?
2. What is consent, as you understand it?
3. How long do you think a couple should wait before having sex?
4. What is your stance on casual sex? If it’s different for men and women, why?
5. Have you experienced kink before? Is it something you want to explore?
6. Would you like to go through a kink checklist together?
7. What’s a sexual fantasy you’d like to try?
8. Is it important to you that both partners get tested before any activity?
9. Whose responsibility is birth control? Should both partners share the cost?
10. How can we make sex better for each other?

Deep flirty questions to ask a guy

While there’s nothing wrong with keeping it casual, some guys like it when you’re more serious. For when you’re feeling more playful, here is a list of ten deep flirty questions to ask a guy:

1. What’s something that not many people know about you?
2. Have you ever fallen in love at first sight?
3. If you could describe me in five words, what would they be?
4. If you had to choose between getting rich and doing something important, what would you pick?
5. What do you think your teenage self would think about who you ended up with?
6. What’s a personal goal you have for our relationship?
7. Is there any thing you’d like us to do more of in our relationship?
8. What’s one good thing you’ve learned from me? What about one bad habit?
9. If you could relive a single moment of our relationship, which one would you choose?

Deep fun questions to ask a guy

Sometimes, you just need a good laugh. Keep things light-hearted with this list of ten deep fun questions to ask a guy:

1. If you could be any superhero, which one would it be and why?
2. What’s the best pizza topping? The worst?
3. What’s a niche subject you wish more people knew or cared about?
4. If you could only ever listen to one artist for the rest of your life, who would it be?
5. If you could have any animal as a pet, what would it be?
6. Would you rather vacation somewhere hot or somewhere cold?
7. What’s something illegal you think should be legal? Vice versa?
8. What would be your last meal if you were on death row?
9. What’s your dream Halloween costume? The best one you’ve ever seen?
10. What’s your favorite so bad it’s good movie?

Some conversations are easier to have when they’re not face-to-face. Here are ten deep questions to ask a guy over text:

1. What’s the most embarrassing thing you’ve ever said or done in front of someone you liked?
2. What’s the weirdest thing that’s ever happened to you?
3. What is the most thoughtful gift you’ve ever received?
4. If you could live anywhere in the world, where would you live?
5. Would you rather live in a studio apartment in a big city or in a big house somewhere rural?
6. Who do you think the luckiest person in the world is?
7. What’s your favorite movie quote of all time?
8. You can bring any dead person from any time in history back to life. Who do you pick and why?
9. What sites did you spend the most time on as a teen?
10. Which is your favorite season? Why?

How to ask deep questions the right way

The thing with deep questions is that they’re not easy to answer by design. This is why it’s important to be thoughtful about how you bring the topic up – choose a time when you’re both relaxed, and neither of you is any rush to get anywhere. Say you want to ask some deep emotional questions, then it’s a good idea to ease into the topic by asking some easier questions first, then bringing up the deeper questions you want to ask once you’re both comfortable.

On the other hand, if you want to ask a sexual question, don’t do it in the heat of the moment. Instead, talking about bedroom activities with a clear head will mean you’ll both be better at communicating what you need and want, making for a better experience once things heat up.

Asking questions is the right answer for a happy relationship

No relationship can survive long-term without good communication, and the key to good communication? Getting to know each other well. That’s why this list of deep first date questions to ask a guy is so useful – it gives you jumping-off points for the kinds of conversations that really strengthen a relationship.

Don’t have anyone to direct these deep questions to? That’s where eharmony comes in. Our unique Compatibility Matching System helps you find partners who share your values and wants in a relationship. Sign up for eharmony and start looking for real love today.