When you’re dating to marry, or even if you’re just trying to think about whether or not this could really work, it’s important to have deep, meaningful conversations with your partner. So here’s a list of 21 serious questions to ask your boyfriend. It’s easy to get caught up in the excitement of being in love, but a lasting relationship requires more than just feelings; it requires intentionality and communication. These questions can help you both think deeper. And they’ll give you practical ideas as you envision your future together.
This list is meant to guide those serious conversations, especially if you’re considering taking the next step toward marriage at some point. Don’t simply ask these questions looking for an answer or looking for the “right” answer. Think about how the answers apply to you.
21 Serious Questions To Ask Your Boyfriend:
1. What is your love language? How do you feel most loved?
Understanding how your partner gives and receives love is critical in any relationship. There are five love languages—words of affirmation, acts of service, receiving gifts, quality time, and physical touch. These are the most known ways people feel most loved. This is an important question to ask because it tells you how to meet your partner’s emotional needs more effectively.
Here are examples of the 5 Love Languages and how they might show up in relationships:
Words of Affirmation
- Saying “I love you” frequently.
- Complimenting your partner on their appearance, work ethic, or how they make you feel.
- Writing love notes or sending sweet texts throughout the day.
- Offering verbal encouragement when they are going through something tough.
Acts of Service
- Doing the dishes or household chores without being asked.
- Running errands for them when they’re busy or tired.
- Cooking their favorite meal or packing their lunch.
- Helping them with tasks they’ve been dreading, like yard work or fixing something.
Receiving Gifts
- Bringing home a small, thoughtful gift “just because” even if it’s just coffee or a candy bar.
- Giving personalized gifts that show you know their tastes (e.g., a book by their favorite author).
- Surprising them with something meaningful on special occasions or milestones.
- Making something handmade, like a photo album or a piece of art.
Quality Time
- Planning a date night where you can connect with no distractions.
- Putting away phones and other devices to give undivided attention.
- Taking long walks together, talking, and sharing experiences.
- Scheduling time for meaningful conversations or shared activities.
Physical Touch
- Holding hands while walking together.
- Hugging, cuddling, or sitting close during a movie.
- Giving a back rub, a massage, or simply resting your hand on their shoulder.
- Offering physical comfort, like a kiss on the forehead or a reassuring touch, especially during stressful moments.
Each person has a different way of feeling most loved, and knowing your partner’s love language can help you express your love in a way that is clear to them.
2. Do I make you feel heard?
Communication is essential. It’s not just about talking but making sure your partner feels understood. Empathy plays a big role in that.
Ask your boyfriend if he feels like you’re truly listening and hearing him out. Ask about ways to improve. This question opens the door for discussing how both of you can improve communication and be better listeners.
3. What’s something I did that you didn’t like but never told me?
Little things tend to build up over time when they’re not addressed. And discovering things about the other person that kinda tick you off is a normal part of the human experience. There might be little things that have bothered him that haven’t come up yet. Getting the answer to this question can help you get an idea of what it’s like to be in his shoes.
Maybe they felt insignificant at the time, but over time, these little things can pile up. This question gives him the chance to bring up any concerns, and it shows you’re open to working on them.
This isn’t supposed to be a question that inspires a personality change. It’s simply a question that empowers you to be considerate. It allows you to get active feedback on things you might be able to improve. You’ll get an idea of how he thinks and learn about things that might contribute to his attitude in his daily life.
4. Have you ever felt like our relationship was one-sided? If so, when?
In any relationship, there are moments when things might feel a bit out of balance. We can’t always give 100%. It’s important to know if your partner has ever felt like they were putting in more effort than you, or if they’ve felt neglected. Was this a one-time thing? Or would he describe it as a part of the culture of the relationship? By addressing this, you can make sure the relationship stays healthy and balanced.
5. Is there something you’ve been holding back from telling me, but think I should know?
Honesty is everything. Sometimes, there are things your partner might hold back, either to protect your feelings or because they’re not sure how to bring it up. Ask this question to clear the air and so you know there’s nothing hidden between you two.
SERIOUS QUESTIONS TO ASK YOUR BOYFRIEND
6. Do you think there’s an aspect of my personality that pushes you away?
This is a vulnerable question to ask, but it’s important if you’re committed to growing together. Nobody’s perfect, and if there’s a part of your personality that he struggles with, this is the time to talk about it and figure out how to navigate it together.
Sometimes people tend to get frustrated in relationships simply because one person thinks very differently than the other. People thinking differently is normal. That’s why values matter. Two people can agree on the foundation of a topic but just disagree on the logic leading to the conclusion or the way to solve the problem. This is an example of something that can be worked through as a team.
It might point to an area of incompatibility though. So be ready. If his answer has to do with an area of your life that you’re aware of and actively working on, then it can be a good question to get feedback.
But if he mentions something about who you are intrinsically, I’d be skeptical. Is he overlooking something you deeply care for? Is he minimizing a concern? Is he unaware of a main priority in your life?
7. Have you ever been hurt by something I said or did, but we never discussed it?
Unspoken hurts can linger and damage a relationship. Especially over time. This question makes room for the other person to speak up for themselves and get something off their chest. It’s important to address any unresolved feelings and make room for healing. If he’s been hurt by something you’ve said or done, now is the time to talk about it openly and work toward a resolution.
There’s this saying: “You don’t know what you don’t know until you know it.“
The answer to this question can allow you to look back on the situation with both perspectives. It helps you to see how they acted in a moment when they were dealing with offense. And it also helps you reflect on ways you can be more considerate of your partner in the future.
8. Is there any part of your life you feel I don’t understand or acknowledge?
Sometimes, we can get so caught up in our own lives that we miss parts of our partner’s world. Asking this question shows that you care about his experiences and want to better understand him. He might bring up something like family obligations or hobbies. Be ready for anything.
Your life and your world is a reflection of all the things you love, all the things you value, and all the things you hope for. The same is likely true for him.
9. Do you feel I support your dreams and ambitions as much as I could?
Your partner’s dreams are important, and being a supportive partner is essential for a healthy relationship. Ask him if there’s more you could do to encourage him in his career, personal goals, or passions.
Sometimes men need verbal encouragement, practical help and support, and sometimes they just need space. In this conversation, think about if you have genuinely expressed a belief in his abilities, if you’ve offered words of encouragement when he’s doubting himself, and whether or not you have celebrated his milestones.
Have you attended events, practices, or meetings related to his interests? Have you offered to help with tasks that align with his goals? Sometimes it’s simply about supporting in one area while he takes care of another.
Check to see if he feels like you have given him space enough to focus on his goals without distractions and feels encouraged to spend the time to do what he’s interested in.
10. Have you ever felt judged by me? If so, about what?
Judgment can create walls in a relationship. If he’s ever felt judged by you, even unintentionally, it’s important to address it and make sure he feels safe being himself. Asking this question gives him the chance to be open about those moments.
When you ask if he’s felt judged, it shows vulnerability on your part and a willingness to listen. His response can also show how safe he feels with you. This is a good conversation starter when it comes to understanding the difference between perception and intention in this specific relationship dynamic.
There could be moments when something you said or did was perceived as judgment, even if that wasn’t your intention. By hearing his perspective, you can gain insight into how your words or actions affect him emotionally. That can help you with your approach in the future.
If he has felt judged, it may also point to insecurities or vulnerabilities he’s dealing with. That’s a good chance to offer reassurance and understanding. His answer can show you areas where he needs more empathy or support.
11. Is there a moment when you felt I wasn’t there for you when you needed me the most?
Life gets busy, and sometimes we might miss a moment when our partner needs us. There may have been a moment when your partner felt unsupported or overlooked. You may not have realized something was important to him. This question opens the door to discussing any missed opportunities to support each other and how to be more present moving forward.
This question can help create emotional awareness, improve communication, and allow you to show up more effectively. Learning about these moments helps you avoid repeating the same mistakes in the future and be more tuned into his needs.
It’s a good space to ask what emotional support looks like for him as a man.
Hearing about his perspective can deepen your empathy and understanding of his emotional needs, especially during tough or vulnerable times. You might realize that he processes stress or hardship differently, and this can teach you how to offer better emotional support when needed: whether that’s by listening more attentively, being physically present, or offering encouragement in a way that resonates with him.
This question can show a commitment to personal growth, willingness to learn, and humility, especially if you genuinely care about the relationship and want to be a better partner. The conversation can also lead to deeper bonds if you’re both able to reflect on things that make you feel cared for in tough times.
SERIOUS QUESTIONS TO ASK YOUR BOYFRIEND
12. Do you feel there’s a part of yourself you can’t express around me?
Relationships thrive on authenticity. If there’s a part of him he feels like he has to hide, it’s important to create a space where he can be fully himself without fear of judgment.
Both partners in relationships need to feel safe and comfortable being themselves. His response here could highlight things he thinks you may not accept. If he does feel like he can’t express certain things, it could be a sign that there are barriers to growing more connected.
There’s also a chance his answer may come from some past experience, maybe the way you handled something in the past. Make sure that you don’t get defensive and really try to hear him out.
13. What are your long-term goals in life? What is your vision for the future?
Knowing your partner’s long-term goals helps you determine if your visions align. Do his goals and your goals match? Whether it’s career aspirations, financial goals, family planning, or personal growth, it’s important to know what he’s working toward and how that fits in with your own plans. Asking this question can also help give you an idea of his intentions, if he has any. Intention is a lot like having an end goal. His outlook for the future should be determining a lot of the steps he takes and the decisions he makes.
I’d be cautious about someone who doesn’t know how to answer this question. That would tell me that they’re not moving in any particular direction. They’re not thinking about what they want.
14. How do you handle stress and difficult situations?
Everyone handles stress differently. Understanding how your partner deals with challenging times gives you insight into how you’ll face struggles together as a couple.
If possible, I would even press to ask if he can describe certain stressful situations that have come up in his life before he met you. What was the most challenging thing he went through? How did he handle it? How long did he have to manage the problem until it came to an end? (That would give an idea about his level of endurance.) What was his mentality like? Did he have a support system? (Men need people they can count on, whether they know it or not?)
When he was in the middle of it all, was he able to talk about it? These questions are going to inform you about his stress tolerance, how he behaves, and if communicates under pressure. It can give you an idea about how to be there for him, especially if he’s a private person.
15. How do you envision our relationship evolving in the future?
This question allows him to share how he sees your relationship growing. Does he see marriage, kids, or other milestones?
Apart from all the life changes, this question also kind of forces you both to have an accurate and realistic vision of the present in each other’s eyes. How are you describing the relationship now? What are the things you guys are just now learning about each other and expect to be more used to as time goes on? Do you think as time goes on you two will be better suited to each other in your relationship dynamic to handle conflict more effortlessly? Speaking of conflict…
16. How do you deal with conflict in a relationship?
Conflict is inevitable, but how you handle it makes all the difference. Knowing his normal approach to conflict resolution can be a really powerful tool. It’ll give you an idea of his mentality when he’s working with a partner to solve a problem. If the conversation goes deep enough, you might also be able to gain an understanding of the types of problems that usually come up for him. You’ll see if there are any patterns. And you’ll be able to be forward-thinking with how you might approach him if and when something comes up.
SERIOUS QUESTIONS TO ASK YOUR BOYFRIEND
17. What are your non-negotiables in a relationship?
Everyone has dealbreakers. Knowing what his non-negotiables are can help you understand where his boundaries lie and whether you’re compatible in those areas. When it comes to relationships, having non-negotiables is key to maintaining your sense of self and ensuring that the relationship aligns with your core values.
Here are some examples to get you thinking ahead:
- Respect: This is foundational. If there’s no mutual respect, it’s hard for any relationship to thrive. Respecting your mind, your body, your heart, your opinions, your quirks; can all be things to talk about.
- Honesty: You need to be able to rely on your partner to be truthful with you. Transparency in communication is essential.
- Shared faith or values: For many people, because it shapes so much of their worldview, having the same religious beliefs or values is important.
- Commitment to growth: This one does not come up very often. But whether individually or as a couple, if one person is striving to improve and the other is stagnant, it creates an imbalance.
- Loyalty: Faithfulness is a big one. Knowing that your partner is committed to you and only you is a non-negotiable for most people.
- Emotional availability: Being in a relationship with someone who is emotionally unavailable can be draining. You deserve someone who is present and willing to engage on a deeper level.
- Clear communication: Partners should be committed to being open and clear with each other, especially in tough times.
18. How do you prioritize work, family, and relationships?
Life is all about balance. Ask him how he manages his priorities and where your relationship fits in. This can also help you figure out how to support each other in achieving balance.
If this isn’t entirely a thing that applies right now, talk about it in a future sense.
Ask him: if we were married and had kids, we’re both working (in this or that capacity), and wanted to make sure we were seeing our extended family and friends, what would that look like in a week, a month, a year?
Do you have family out of state? How often would you like to see them? How often would you try to do date nights ideally? Would you guys do family days or family dinners? Do your current work schedules conflict with what you might envision for the future?
19. What are your views on managing finances as a couple?
Money can be a major source of conflict in relationships. Discussing how you’ll handle finances before marriage can help set you both up for success. Think about paychecks and budgets, investment accounts, retirement accounts, savings accounts. How would you go about spending for hobbies or other extra things? Would you want to have a joint account or separate accounts or both? Are you willing to be transparent with transactions in both cases?
Do you anticipate any spending habits changing as you have kids? Do you care more about having an emergency fund in that case? What about investing when you have kids? Do you care more about managing and calculating risk when you have kids?
This would be a good time to brainstorm and sort out those details.
SERIOUS QUESTIONS TO ASK YOUR BOYFRIEND
21. How do you handle feelings of jealousy or insecurity in a relationship?
Jealousy and insecurity in a relationship should not be the norm; it should be the exception. But there are some times when those feelings come up.
People typically assume jealousy means that someone is jealous of their partner spending time with the opposite sex, or they’re jealous that another person is showing overt interest in their partner.
People assume that insecurity is due to low self-esteem. I want to challenge you to think more broadly.
Your partner may at some point feel jealous for your time. They may feel jealous of your enthusiasm toward something. They may feel jealous for your trust and want you to feel like they are your go-to person to talk to.
Generally speaking, partners should feel confident in their partners loyalty and confident of their own emotional safety in the relationship. Insecurity can come up for a variety of reasons. It can be due to attachment styles. It can come up if someone makes a comment that makes the other question the stability of the relationship.
It can be insightful to know the types of things that might make you or your partner jealous or insecure. This is a good opportunity to talk through how to wrestle with those feelings, how you react or respond, how to bring your feelings to your partner, how to think differently, or how to keep it from happening again.
I’d say more often than not, if you and your partner typically have great communication patterns and are relatively transparent and usually able to talk through difficult conversation productively, if these feelings come up and your normal methods are not working to bring resolve, there may be something deeper going on and those feelings might be coming up from a past trauma. So if you get to that point, you can still be pragmatic (sensible and practical) but also focus on being empathetic and gentle with the other person.
BONUS: Here’s a list of extra questions I would ask.
- Since I’m a single mom, how do you envision your role in a blended family? Are you clear on my boundaries when it comes to my child and will you respect them?
- Do you feel like you are able to communicate your thoughts and feelings? If I ask for more communication in certain areas, would you be willing to work on that?
- What’s your approach to doing something that you don’t want to do but know you should do? (Apart from work)
- If we were married, would you be willing to go to marriage counseling every once in a while?
- What are some things you would need or look for when it comes to a spouse?
- How often do you talk to God about the details of your life? (If at all)
- Do you look for opportunities to grow in your relationships? Is that something you’ve ever consciously done before?
- What do you think it takes to build a strong, lasting relationship?
- How do you feel about sharing/dividing responsibilities (e.g., household chores, parenting, grocery shopping)?
- If we were married, and you got to a point where you felt you didn’t want to be married anymore, what would you do?
- Do you feel like you have an accurate understanding of what I’m looking for long-term? If yes, tell me.
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