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21 Questions To Ask In Order To Really Get To Know Someone

The older we get, we often seek more meaningful connections than teenagers looking to be friends and accepted by everyone.

Love & Relationships

Whether it's an acquaintance, co-worker, new friend, or new date — we have to be open to asking strategic questions to get to know each other a bit more in-depth. Asking the right questions can take you a long way to determine how much of your time and energy do you want to spend with another person. We all can help each other grow, but it starts with being a little vulnerable to see what things you can enjoy together or what might be triggering for that person and may require you to lead with caution.

Here are some questions you should consider asking someone you want to know on a deeper level:

1. What’s your favorite love languages?

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Learning someone's love language allows you to understand how that person prefers to show and receive love. There are even quizzes you can take to discover your love language before you ask others. Created by Gary Chapman, the five love languages are quality time, acts of service, words of affirmation, physical touch, and gifts. And although they are commonly used to refer to romantic relationships, love languages can be applied to every relationship in your life, including the one you have with yourself.

2. What are your short-term goals?

Asking what someone's short-term goals are allows you to see if they are a person with a plan instead of living life with no direction, and you could see how realistic their goals are based on what they are doing now to achieve them.

3. What are your long-term goals?

Long-term goals are where our dreams live! Hearing a person map out the little steps shows you how strategic and serious they are about accomplishing their objectives. Are they just a dreamer or an active achiever? If they want a family, how are they holding themselves accountable in existing relationships and working things out instead of canceling everyone? Are they securing their financial bag to invest in their dream company, or are they splurging going on ten vacations a year and not saving a dime?

4. What's your relationship with your family like?

Asking questions about family relationships is essential because everyone has a unique connection with their family. For some people, family can be so exhilarating to talk about, and for other people, it could be a nightmare and a huge trigger of emotional distress. Our family has a lot of influence on us, whether we like it or not, so knowing their relationship will help you understand why they haven't called a family member in years and how that reflects in other relationships in their life.

5. What happened in your last relationship that led you to break up?

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This is a great window to see how accountable that person is because even though we all get hurt, we also play a role in every situation. Some situations are toxic, some people grow apart, but overall, there is always a lesson to learn and things to admit we could have done better.

6. What relationship in your life do you find the hardest to navigate in?

Learning what relationship is the hardest to navigate lets you know when you need to give this person a bit more space when he/she interacts with them. There may be a time you're around that person when they answer a call from the person they find the hardest to deal with, and all they need is the "Hey, how'd it go with so and so," "Are you OK," or "I'm here if you want to talk about it."

7. What scenarios in life are you most afraid of?

We all have scenarios we are afraid of but appreciate greatly, like I can't wait to be a mom one day, but I'm nervous about the pregnancy journey because of the high statistics of Black women not being believed when they are in pain or other health complications. So if a friend/your partner knows this, they can help comfort you and advise books, articles, podcasts, other great resources to prep for this stage in your life. And there are some scenarios that a person could never want to encounter, and talking about them can help you acknowledge their boundaries.

8. Do you enjoy reading, and what books do you like reading?

Some people are avid readers, others read a book here and there, and some don't read at all. So if you want to have a little book club to review your favorite novels with this person, it's great to ask them how often do they read and what genre they enjoy reading. Maybe they could be your reading accountability partner to pencil in 30-minute to an hour reading sessions daily or vice versa, but you won't ever know unless you ask.

9. What is your best and worst quality?

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Asking someone their best and worst quality shows you how self-aware and honest they are. I'm sure after they tell you their worst quality, they'll follow up with the list of things they're doing to change that quality. Top tier bonds are rooted in transparency.

10. Are you a messy or neat person? Are you on time or usually late?

Listen, ladies, these may seem like simple questions, but they are critical when you have tickets to a concert, and you end up missing it because this person is three hours late. And then, on top of that, you plan to stay over this person's place after, and it looks like a tornado hit their room.

So asking if someone is messy or clean allows you to initiate the "Hey, since I'm staying over tonight, can you tidy up a bit, so I don't feel so out of place." And some people only know CPT (colored people time), aka late, so you need to know if you need to tell them an earlier time so they can come on time versus two hours late.

11. What type of music genres do you like most, and do you enjoy going to concerts?

Music is the world's universal language; knowing this person's favorite music genres can show you more about their character. Some people are diverse music lovers, and some people only like one or two genres. Either way, you can gauge music review conversations, and it could let you know if you have a potential friend to accompany you at concerts and festivals.

12. Who was your childhood hero?

Our childhood hero holds an extraordinary place in our hearts; mine is my mommy; I was very close to her as a child, and I cherish the relationship we have in adulthood. But learning the inside scoop on this person's childhood hero could let you know why they may have admired that person or even if that person is still around to tend to them.

13. What celebrity do you admire the most and why?

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This is great info to get a hold of because it can show you what characteristic traits people value in others. Mine are J.Cole and Prince because they're both unapologetically authentic, private, and talented, not looking to please the world but be true to their craft and themselves. So asking this question can show you genuine or artificial traits they may value in others.

14. Are you religious or not?

Everyone has a very different experience with religion; some people could have only gone to church because their family demanded them to, and now they are agnostic or are new Christians and are seeking a church home on their own terms. Religion creates structure, and it shows you what people value, so it's essential to know where they stand in this area to have faith-based conversations.

15. How do you deal with finances, do you spend too much or too little?

Managing finances is a prime topic to see if this is a potential roommate, someone you can plan a vacation with or build a family with. Regardless, money matters as we all know as adults, so it's essential to discuss financial goals to respect if someone can't tag along for a vacation because they're saving up to move out of their parent's house and investing in going back to school to earn a higher degree.

16. What political party do you align with and why?

Politics and religion are mandatory to discuss in any or every relationship. People's political views say a lot about their character and what they invest their money in. This is a serious matter you have to be mindful of because the same things you are raising your voice about, they may be indifferent about and vice versa. Are you able to handle that?

17. What past mistakes do you regret the most and why?

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Regrets are also useful to address because it shows you people's growth. Nobody needs a stagnant person who claims they did their best in everything; we all mess up from time to time, but we learn from those experiences that mold us and allow us to do better.

18. What do you need when you're stressed out? Do you like to talk it out, journal about it, or just want to deal with it alone?

Stress, stress, stress! I know we all hate being in this mindset but discussing what you need in stressful moments (prior to the situation) allows you to respect how that person may process negative emotions, and it shows you how you can support them during that time frame.

19. What's your ideal vacation?

Don't we all love the sound of VACATION? I know that's a yes sis, where we going, and how much do I need to save prior?! Inquiring about how people like to vacation is a mega tip for you; it shows you if that person just wants to sleep all day and party all night or the opposite and plan ahead to do all the sightseeing, visit museums and cute restaurants. It's a plus for you if you think this is a good person to invite on your small friends' trip to Costa Rica or just pass altogether on the invite.

20. What's your biggest fear?

Asking someone their biggest fears lets you know where they're the most vulnerable and may need extra support when they face seasons that trigger their fears.

21. What's your biggest flaw?

I know no one is jumping up right away to say their biggest flaws, but it's great to highlight, it shows us we're self-aware, and it leads to conversing about better ways to overcome those flaws. Who says you can't be flawless in a few months if you have the tools to combat your flaws?

The journey of getting to know someone is a beautiful process, but the older we get, we often seek more meaningful connections than teenagers looking to be friends and accepted by everyone. We can't be afraid to dig a little deeper to see our loved ones' core and vice versa to build more lasting relationships built on sturdy foundations!

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