No matter what you claim are the “must-haves” of a good boyfriend, no relationship can survive without effective communication. Two people trying to build a life together will face multiple hurdles. From navigating cultural differences to deciding who wants how many children (if any), there are plenty of reasons why having “the talk” in a romantic relationship is essential.
This doesn’t mean you have to sit down with your beau and interrogate them like you’re a PI trying to solve a whodunnit. But at different stages in your relationship, you’ll want to check in and ensure you’re both still aligned. If you aren’t, maybe you can course correct. Or, maybe it’s a sign that the relationship’s run its course and it’s time for you two to split amicably. Check out these top questions that are designed to help you gauge compatibility, better understand your partner, and also dig deeper into what you need in a relationship so that you feel fulfilled.
What to Remember When Posing Questions to Ask Your Boyfriend
No one wants to feel interrogated, so try to pose these questions in low-stress scenarios. When you’re 10 minutes into an argument, that’s not the time to suddenly start rattling off a list of questions. You’ll come off as judgmental and usually, this method will backfire. Leave your judgment at the door and use these questions as a simple way to get feedback. You want this exercise to be a safe space for him to be open and honest with you.
But pay attention to more than just what your boyfriend says. Also consider how they respond, if they get uncomfortable when you ask certain questions, or even if their body language suddenly changes. Do they become closed off when you dig into certain topics? Do they evade by creating a word salad response that never actually answers the question or shifts the conversation to a different subject?
17 Compatibility Questions to Ask Your Boyfriend
These days, people don’t always have the formal “let’s be official” conversation where two casually dating people suddenly become a full-blown couple. It’s very easy for a situationship to magically become something more simply because neither party bothered to define the relationship while months turned into years. If you’re in that scenario, and a friends with benefits has suddenly become more, you better start asking questions before you’re three years in and realize that he’s not the one because of diametrically opposed beliefs.
Do you believe in monogamous relationships?
Polyamory and open marriages are growing in popularity. But buyer beware. Some people often feel pressured to agree to this when it’s not what they want. If you’re genuinely okay with an open relationship, then this can be a fun new world to explore that enriches your relationship. You still need to set boundaries and expectations for what constitutes acceptable exploration.
But if you’re a one-man woman, don’t lie and say you’re cool with a poly or open relationship if it leaves you feeling empty or like you’re not enough. Stand up for yourself and recognize that this might be a deal breaker. Similarly, don’t forget to follow this question up with “and what if I want to explore having other partners?” Somehow, the polyamory and open marriage conversation is all fun and games until it’s the woman tasting the rainbow.
Other Compatibility Questions to Ask Your Boyfriend
- What do you think are your best qualities?
- How do you feel about me regularly going out with my girlfriends?
- How do you feel about me having male friends?
- Do you believe in marriage?
- Do you want children? If so, how many?
- Are you financially responsible?
- Do you have long-standing unpaid debt?
- How is your credit?
- Do you want to buy a house?
- Do you like dogs/cats/pets?
- Do you like living here? Would you ever relocate?
- Do you actively practice a religion?
- Could you be in a relationship with someone who was either an atheist or practiced a completely different religion?
- What are some beliefs you grew up with that you no longer hold?
- How do you feel about investing?
- Do you feel generational wealth building is important?
16 Relationship History Questions to Ask Your Boyfriend
Yes, the past is the past. But beware the man who claims that all his past relationships failed because of the ex. Everyone has to take responsibility for the role they play when a romance sours. A man who is always the victim and can’t own their hand in why a relationship failed is a walking red flag. If your boo refuses to ever be honest about what happened in past relationships, or always claims that their hands are entirely clean, run. Incidentally, the same applies to you.
Are you still friends with your ex(es)?
This is a question that is just as much about you as how your boyfriend replies. Some people believe that exes belong in the past and they don’t want to keep in touch. Others act like they’re Thanos with a gauntlet of exes. This doesn’t always mean that someone is up to no good, but check in with yourself if you have an ex that doesn’t cut ties. Sure, they might be the type who can be really good platonic friends with a former love. Or, it could be them always wanting to leave the door open. More importantly, how do you feel knowing that former flames may regularly pop up in casual conversations or at get togethers?
Other Relationship History Questions to Ask Your Boyfriend
- Why did you break up with your ex (or your longest relationship partner)?
- What’s the longest relationship you’ve been in?
- Have you ever been married (or engaged)?
- Who was your first love and why did it end?
- Do you have a type?
- What did your past relationships teach you about love?
- Have you ever cheated on a partner?
- Have you ever had your heart broken? If so, what happened?
- Do your friends hold you accountable in a relationship?
- What is something you did in a past relationship that you regret?
- Would you want your sisters or female relatives to have a partner like you?
- What are the key traits you want in a romantic partner?
- Do you think that people can change?
- Do you have a defining relationship that made you change how you act as a boyfriend?
- What was the worst first or blind date you ever went on?
16 Deep Questions to Ask Your Boyfriend
Compatibility is about more than simply wanting 2.5 children, a four-bedroom house, and two dogs. It’s also about seeing eye to eye on different cultural or life issues. From politics to religion, these are the questions to ask to make sure that you’re not dating an atheist if you’re a devout Christian or with a raging mysogynist when you’re fighting for women’s rights.
Do you believe in equality regardless of gender and sexual orientation?
Yup, this is a loaded question. But in our community, equality is intersectional. And given current political sentiments, this is a question that might have surprising answers. We’ve all seen TikTok videos describing people who claim to be liberal but are dating incredibly conservative people and it feels like a disconnect.
Does your partner think that an independent woman who earns her own money is a good thing? Or is it a threat to their masculinity? Meanwhile, do they think that LGBTQIA+ members deserve equal protection under the law? It’s hard to be in a relationship with someone who’s views are so polar opposite to your own.
Other Deep Questions to Ask Your Boyfriend
- If you could do any other job than the one you’re currently in, what would it be and why?
- What are your five-year or 10-year plans for yourself?
- How do you want to be remembered?
- What causes are most important to you?
- Do you believe in therapy?
- How do you measure success?
- If money wasn’t an issue, what would you do with your life?
- Do you believe in giving to charitable causes?
- Who is the person that’s your go-to individual when you need help (besides me)?
- What are your fears?
- What’s something you can’t live without?
- Who is your best friend and why?
- How have you grown in the past five years?
- If you could tell your childhood self anything, what would it be and why?
- Have you ever lost a friend because of a disagreement? How did it make you feel?
14 Important Questions to Ask Your Boyfriend
Relationships aren’t just about sex, they’re also about building and growing together. Yes, good sexual chemistry will get you through the honeymoon phase. But if you don’t have a solid foundation, when those stars and roses start to wear off, neither of you is going to look all that appealing to the other for long. Real intimacy means feeling comfortable with each other and being willing to face conflict knowing that you’ll get through — and be stronger for it.
Do you feel you can talk to me, even when we disagree?
Communication is critical for any relationship. Of course, there are times when you two might fight and need a little space to cool off. But can your boyfriend go days without speaking to you? Or, do they push for you two to resolve whatever went down earlier? Do they avoid confrontation at all cost (spoiler alert, this is not a good thing)? Or are they willing to have uncomfortable conversations if it means finding common ground?
Other Important Questions to Ask Your Boyfriend
- What are things I do that really turn you on?
- Why do you think people cheat?
- What do I do that annoys you?
- What are your annoying habits?
- Do you think that we fight fair?
- Do you think I listen to you when you’re trying to explain your feelings?
- What’s your idea of a healthy romantic relationship?
- What is your idea of commitment within a relationship?
- Is there anyone besides your parents who you think have a great relationship that you think is #goals?
- What do I mean to you?
- What do you think can make our relationship stronger?
- How can I love you better?
- When do you know you’re ready to say I love you?
14 Spicy Questions to Ask Your Boyfriend
Every relationship needs a little spice, and this is even more important when the honeymoon phase is behind you and you’re in the trenches. If you can’t keep the fires burning and the heart racing, it’s going to be tough going for the two of you. While a lot of attention is paid to how men can turn a woman on, don’t forget that he’s human and has hormones too. Not all men are alike sexually, and he deserves a customized approach to pique his libido too.
What’s something I can do to turn you on?
This can be an open-ended question because you want your boyfriend to be as honest as possible about what gets them going. Maybe they have a kink. Maybe they like to role play. Or, maybe they want you to be dominant. Just remember that this is a judgement-free zone. So, no shaming, and no harping on a particular kink that might not appeal to you. Remember, you don’t have to do everything right away. But make a mental note of the topics that get him excited.
Other Spicy Questions to Ask Your Boyfriend
- Do you want me to initiate sex more?
- What are some unexpected hot spots?
- Do you want to be more adventurous in the bedroom?
- How do you feel about sex in public?
- What’s your favorite p*rn category?
- What’s your ultimate soundtrack for having sex?
- How do you feel about sex toys? If you’re open to them, which kinds do you want to bring into the bedroom?
- What’s the most sexual act you love that’s not actually sex or foreplay?
- Do you like dirty talk?
- What do you think about sexting?
- How do you feel about being filmed while having sex?
- Do you ever send nudes?
- Is there anything that immediately would turn you off from having sex?
13 Family Questions to Ask Your Boyfriend
Your family unit and the relationship you have with various members in that group is so important. These are the first people you learned to connect with, and they also shape your worldview. For example, a man who has a difficult relationship with his mother might struggle with intimate relationships with women. Meanwhile, a man who’s a little too attached to his mom and turns to her over you might not be independent — meaning you can have an overbearing future mother-in-law on your hand.
What is your relationship like with your parents?
Every family dynamic is different, but hands down, your parents are the first people you bond with. So, if you have an incredibly rocky relationship with them, it’s highly likely that those awkward behaviors are going to spill into other areas of your life — including romantic pairings. Do your boyfriend’s parents have a close relationship with him? Does he feel he can talk to them about anything? Or is he constantly complaining about feeling judged or ignored within the family group?
Other Family Questions to Ask Your Boyfriend
- Who are you closest to in your family?
- Do you have a close relationship with your extended family?
- Did you spend a lot of time with your family?
- Does your mom like me?
- Does your dad like me?
- Is there anyone in your family that you refuse to talk to?
- What’s your favorite memory from your childhood?
- Are there any memories that were traumatic from your childhood?
- Are your parents still together?
- What’s something you learned from your parent’s relationship that you think is important for your own?
- Was there anything you wish you had experienced as a child?
- What do you think is the most important thing you should teach your future children?
10 Emotion Questions to Ask Your Boyfriend
Historically, men haven’t had the same freedom as women to express emotions beyond perseverance, anger, and pride. Thankfully, society is pushing back on outdated toxic masculinity tropes and pushing men — and the women around them — to encourage men to lean into their feelings and not pretend that they don’t experience sadness, frustrations, or even depression.
How do you manage negative emotions?
Understanding how your boyfriend handles emotions can foreshadow whether they’ll turn to you when bad things happen, or bottle them up inside. More importantly, if you’re the one causing frustrations, do they view you as a safe space or as someone to be avoided?
Other Emotion Questions to Ask Your Boyfriend
- If we were having relationship problems, would you be willing to go to couples counseling?
- Do you believe in individual therapy?
- What’s a time that you got very angry, and how did you handle it?
- Do you think you’re good at handling stressful situations and emotions?
- How do you express stress?
- Do you have healthy ways to release stress?
- Are you comfortable with expressing your emotions?
- Are you comfortable crying in front of me?
- When was the first time you realized that your parents weren’t super heroes/perfect?
10 Romantic Questions to Ask Your Boyfriend
Keeping the romance alive is key to maintaining a sense of magic in your relationship. By asking questions that spark a touch of romance, you can remember why you fell in love in the first place, especially during times when you’re confronting more serious themes in your partnership.
What’s your love language?
Getting to know your partner’s love language is all the rave these days, as it helps to better express your love for one another in the way that they understand best. While some need physical touch in order to feel appreciated, others may need words or acts of service, and knowing can keep the spark alive between you while making sure you’re both emotionally satiated.
Other Romantic Questions to Ask Your Boyfriend
- Would you rather be the first to say “I love you?”
- What’s your ideal date?
- When did you realize I was the one?
- What’s the most ideal future you envision for us?
- How do you want my love for you to be expressed?
- Is there something you’ve been too shy to tell me?
- How do you want to maintain the honeymoon stage?
- Do you feel safe in our relationship?
- Describe a perfect day together.
