Questions To Ask Your Boyfriend Before Things Get Too Serious

Don’t take things to the next level until you’ve had "The Talk".

Questions to ask your boyfriend

(Last Updated on May 24, 2020 by Datezie Editors)

If you’ve been dating someone for a while and you’ve barely scratched the surface on true compatibility, you’re not alone.

 “In today’s society, it can be difficult to ask tough questions before getting serious with a boyfriend,” says relationship expert, Carmel Jones.

 “Tough or not, though, it is important. “In asking questions, you can assess the quality of the answer,” adds Dr. Logan Jones, psychologist and founder of NYC Therapy & Wellness.  

 While a round of 21 questions may be frowned upon on the first date, true compatibility testing needs to happen at some point ideally before things get too serious. Doing so could save you a lot of time and heartbreak. 

“For example, if you’re asking important questions about the future, your wishes and the life you want to create and if you are getting answers that are vague, uninspired, generic or uninformed, you may want to ask yourself, ‘How serious is this person about this?’ If the quality seems low, then that’s a time to pause and reflect.”

 The bottom line then becomes about solving this: are we in the same relationship?

 “If you can’t say ‘yes’ or ‘I think so,’ you need to re-evaluate things,” says Dr. Jones. “You want to be cautious when you wonder if you are in a relationship where you have two different ideas about what you’re doing or where you’re heading, even if it’s a casual fling. If you ask this question and you can’t say ‘yes’ or ‘I think so’, then you need to consider walking away before things get too serious.”

 Ready to go deep? Here are the questions you should be asking your boyfriend before things get too serious.  

Questions about loyalty


Do you believe in monogamy?

Do you want to get married?

What are you not willing to change for a relationship?

 Why do you think you’re ready for a relationship?

What kind of compliments do you like to hear?

 What’s your communication style?

 When you’re stressed out, how can I help you?

How often are you open with your feelings?

What are your relationship deal breakers?

 What does marriage mean to you?

 What’s a romantic date for you?

 List the best qualities you have to bring to a relationship.

List the qualities you desire in a relationship.

How long was your longest relationship? Why did it end?

 Have you ever lived with a girlfriend?

Am I the right person for you?

 What do I mean to you?

 How big of a deal are special occasions?

 Do you wish anything could change in our relationship?

If I got into a disagreement with one of your friends or family members, how would you handle it?

 What’s your favorite memory of us?

 What about me caused you to fall in love?

 If our relationship ended, what would you miss most about me?

Have you ever been in a long-distance relationship?

 If one of us had to move away for some reason, would you attempt long distance? Or would we go our separate ways?

 Do you have my back no matter what?

 What does love mean to you?

What’s your idea of a healthy relationship?

Do you believe in soulmates?

Questions about past relationships

What’s the most important lesson you’ve learned from past relationships?

What are your biggest fears in relationships?

What’s one thing you regret from your past?

 Who was your first love and why did it end?

Questions about family


Do you want kids?

 What would you do if I got pregnant?

 What would you do if we struggle to get pregnant?

If we have kids, what’s your parenting style?

 What kind of education do you want to provide for your kids? How do you plan on paying for this?

How’s your relationship with your family?

 What do you think of my family?

 Who is your role model in life?

Have you ever dated someone that your family didn’t like?

What did you learn about marriage from your parents?


Questions about infidelity

Have you ever cheated?

 Have you ever been cheated on?

 What do you consider cheating?

 If I said you could date another person, would you?

What’s something that causes you to lose trust?

What’s the biggest lie you’ve ever told?

Questions about finances

What are your financial goals?

 Are you in debt?

 What financial obligations do you have?

 What’s your credit score?

How much money do you need to make in a year in order to feel financially secure?

Should a couple’s finances be joint or separate?

How are you going to save for retirement?

Questions about intimacy

Is sex important to you?

How often do you like to have sex?

If there anything that makes you uncomfortable about sex?

 Are you an affectionate person?

What’s your favourite part of a woman’s body?

 What’s your favourite non-physical quality about me?

What’s your favourite part on your body?

How many past sexual partners have you had?

 What turns you on? What turns you off?

 What’s your sexual fantasy?

 What’s the best gift a partner could give you?


Questions about their personality

What were you like in high school?

What object can’t you live without?

What’s your worst habit?

What’s your perfect date?

What would your exes say about you?

What have you learned from past relationships?

What are three words people would use to describe you?

Do you think you have a type?

What makes you tick?

Do you have a temper?

If we had a bad fight, how would you resolve it?

What’s the angriest you’ve ever been?

 How can I tell that you’re stressed?

What are your biggest fears?

What does it mean to forgive?

 If you could travel anywhere, where would you go?

How do you feel about pets?

 Are you allergic to animals?

 What’s something you tend to procrastinate about?

What is one behavior that you would never tolerate?

How much do you think you’ve evolved over the past several years?

What’s your attachment style?

Do you like to divide up chores?

 How important is a clean house for you?

 How do you feel about health and physical fitness? Is it a priority for you?

 If you got sick, would you want me to take care of you?

 When life is hard, how do you handle it?

What’s your biggest failure and how did you grow from it?

 What are you hardest on yourself about?

 Have you ever struggled with addiction?

 Is there anything from your past that you’re ashamed about?

 What accomplishment are you most proud of?

 What are your values?

 How do you make important decisions?

 What’s your favourite personality trait?

 What are some of your guilty pleasures?

 When you were a kid, what did you want to be?

 What makes you vulnerable?

 When was the last time you cried and why?

Questions about the future

 Where do you want to live when you retire?

If you could live anywhere, where would it be?

 What would you do if my appearance changed drastically?

What would you do if I was in a serious accident and had to be taken care of for the rest of my life?

 Where do you see this relationship headed in five years? Ten?

What do you hope comes from our relationship?

What’s on your bucket list?

Questions about religion/politics

How important is religion to you?

 Do you attend church or have other religious commitments?

 What are your political views?

Questions about career

What’s your dream job?

 Can money buy happiness?

 Do you like your job?

Are you secure in your career?

Questions about the opposite sex

 If your partner had a lot of friends from the opposite sex, how would you feel about it?

 Do you compare yourself to other guys?

 Do you have any close female friends?


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