If there’s one thing I’ve learned from my Human Resources career, it’s the importance of asking the right questions when interviewing. And when you think about it, dating and getting to know someone is nothing but a long-ass interview process to see if you want to hire the person on a full time, part-time, or temporary basis. The other person is most likely interviewing you as well.

Think about it. If you’re interviewing, you will likely review the organization’s website to find out about who they are, what they do, their culture and core values, mission, vision, leaders and influencers, their social media posts, LinkedIn page, and maybe even their Glassdoor reputation. 

And this all happens before the interview. During the interview, you’re asking questions about the role’s responsibilities and expectations as well as what it takes to develop and grow within the organization.

Why don’t we approach dating with the same systematic and strategic approach? Matters of the heart are not exempt from the need for due diligence. If you’re looking for a committed relationship, it is smart to ask the right questions and really, really listen to what’s said and what’s not said. 

Sound like a lot of work? It is! But it’s worth it and could save you some time and energy, give you clarity, and possibly even protect you from a heartbreak or two. Oftentimes, relationships crumble because things are either not known or not addressed early in the union.

Now, there are no right or wrong answers, only answers or responses that either align or misalign with WHO YOU ARE and WHAT YOU WANT. Of course, before you begin dating, you should have already put in the time and effort to fully and authentically explore this. 

Also, keep in mind that you do NOT want to ask all these questions on the first date. These questions should be sprinkled into face-to-face conversations and phone conversations (but not text messages). This shouldn’t feel like the Spanish Inquisition so be conversational and inquisitive. Most people like to talk about themselves so you’ll notice that you may get responses to multiple questions if you just let them talk.  If you see this person at least once or twice a week, you’ll probably have most of these questions answered in the first month, maybe later if you see each other less frequently.

If you’re dating for fun and not looking for a relationship, read on anyway because you STILL need to know these things so that you have a full understanding of the quality of the person with whom you’re sharing your time and energy. You never know, you might fall for this person unexpectedly (damn, Cupid) so at least you’ll know what you’re working with.

Some of these questions are awkward as fuck but try to push past your discomfort and look at it like a jigsaw puzzle and gather one piece at a time. One more thing … don’t read these verbatim like a checklist or email this list to potential partners. It’s creepy and impersonal. Like I said, just sprinkle these questions into the conversation as naturally as possible and listen actively to their responses. Their responses will tell you a lot about their values, communication style, and perspectives on life.  By the way, the questions with asterisks are THE MOST CRITICAL.

Readiness/Willingness to Commit – These questions will help you to find out if you and this person are on the same page when it comes to wanting a committed relationship.  If he/she is vague or unsure, consider that a “no”. It could mean that they are not ready and not on the same page as you. You may be doing yourself a disservice by proceeding with the hope or expectation that they’ll change their mind or become clear about whether or not they want a relationship. 

  1. What are you hoping to achieve from dating?*
  2. What are your thoughts on monogamy with the right person?*


“No response is a response. And it’s a powerful one. Remember that”

– Unknown


Personality/Style/Interests – These questions will help you to get to know your date and find out a little more about them. These are also great icebreaker/first date questions to warm them up before asking deeper questions later.

  1. What do you do for fun?
  2. If you could create your perfect day, what would it look like? What would you do first? Then what?
  3. What are your pet peeves?
  4. Would you consider yourself an introvert (someone who gets energy from being alone) or an extrovert (someone who gets energy from groups)?
  5. If I were to ask your friends for 3 words that describe you, what do you think they’d say?


Family/Friends/Interpersonal Relationship Skills – These questions help you get to know who is in their circle and what other relationships might be important. These are great questions to segue into whether your date wants children in the future or has them already.

  1. Who is/are about your best friend(s)?
  2. When you need advice, who do you call first?
  3. Do you have children? If so, what is your relationship like with their mom/dad?*
  4. What do you think about having (more) children after you’ve settled down with the right person? How many?*
  5. How would you describe your childhood?
  6. Where does your family live? How often do you see them?
  7. How do you typically celebrate holidays?
  8. When was the last time you had to apologize to someone? What happened?



  1. What do you do to take care of yourself physically?
  2. Do you have any illnesses/conditions? If so, how do you manage them?
  3. What are your favorite foods? 
  4. Any dietary restrictions (vegetarian, vegan, no pork, etc.)?
  5. How often do you cook?
  6. What are your expectations for your partner when it comes to cooking?
  7. Do you drink? If so, what do you drink? How often do you drink?*
  8. Do you partake in drugs (including marijuana)? If so, how often?*
  9. When it comes to your home/space, do you consider yourself a neat freak or someone who might be a little messy?



  1. Do you believe in God or a Higher Power?*
  2. How important are faith and spirituality to you?*
  3. What spiritual practices do you have (church, mosque, prayer, meditation, etc.)?
  4. How would you feel about dating or marrying someone with a different faith or spiritual perspective?



  1. When you were a kid, what did you want to be/do for a living?
  2. What do you do for a living now? Do you like it? If not, what would be a career that you like? *
  3. What goals do you have for your career?
  4. What’s your view on higher education?
  5. If you won 100 million dollars in the lottery tomorrow, what would you do first?*
  6. How do you feel about debt and credit ratings?*
  7. Would you consider yourself more of a spender or a saver? Why?*
  8. What’s the biggest purchase/most expensive thing you’ve ever bought? Was it worth it?
  9. Once you retire, what do you imagine you’ll do every day?

Life Experience & Life Goals – These questions might help you to understand your date’s overall life experiences and how they view the world.

  1. What’s been the most difficult challenge you’ve faced in your life? How did you get through it?
  2. Have you ever been to jail? If yes, be sure to get details on the crime/alleged crime and surrounding circumstances. You can also do search public records or consider investing in a background check.*
  3. What do you think are the most pressing issues in society right now (examples: global warming, race relations, immigration issues, LGBTQ rights)?*
  4. Have you traveled to any cool places outside of the US? If not, how do you feel about exploring other cultures?

Of course, some people are serial daters and they know all the right things to say. But now that you’ve asked the right questions and you’ve actually listened to their responses, the next phase is to watch … stay tuned for Part II: Things to Watch For In The First 30 Days of Dating … and Beyond.