Everyone wants to be an interesting person, and the best way to be interesting is to show interest in others because people always remember how you make them feel. You can do this by asking intriguing questions that help you fuel an amazing conversation that converts strangers into acquaintances, and maybe even acquaintances into something far deeper and long-lasting.
Below we have topics that can stimulate conversations and help you know someone beyond simple small talk topics. This isn't to say there is anything wrong with small talk: it's still good to start with light stuff like the location you chose to meet at, the food you enjoy, and any good music or movies you love, but these topics don't break the ice, and they aren't going to help you get to know someone on a deeper level.
Some tips to remember for conversations, in general, is to wait till the other person has finished speaking before you begin another question or share a relatable experience, to be honest, and pay attention - don't touch your phone. A tip that might be surprising is to let silence happen; don't feel the need to fill every moment with talking.
Giving time to both think and simply be in each other's company is also a way of learning about what it's like to have someone in your life. Getting to know someone beyond the superficial doesn't need to be all serious though. Starting on a high note, the questions below can lead you to get to know someone much more deeply.
1. What Was the Best Decision You Have Ever Made in Your Life?
This one is a nice, positive question that can also get a little deep. It leads the conversation to very important milestones in one's life and can help you get to know more about a person's ownership of their life and their choices. Because it is so open and invites them to explain quite a lot about themselves to you, you will probably get to learn about other important people in their lives too.
If you are a good listener, the answer to this question will give you many opportunities for follow-up questions related to their decision, the results, and the people they spoke about connected to the decision. If they didn't already tell you, always remember to ask why they chose to make that particular decision because the motivation for an important choice can always be an entire conversation on its own.
2. Have You Ever Had a Side-Hustle or Would You Consider Having One?
This can be a good question to see how compatible your lifestyles will be. Many people in our modern gig economy have more than one job and often have other revenue streams that allow them to either keep hobbies that pay for themselves or supplement their income in a rather important way.
This is not true for everyone, but as it is becoming more and more common, it would be a good insight into the person's lifestyle, work ethic, and personal hobbies and interests. If you already have a side-hustle, you may want to find other like-minded people who understand your proactive lifestyle, and this is a good way of identifying whether someone fits in that category.
If you hope to connect with someone who has a lot of free time to spend with you, your schedule may clash with a busy person who has added obligations from a side hustle.
3. What Got You Into Your Current Line of Work?
Let's skip that tired old question of "what do you do?" as the first thing asked. People are more than just their jobs, so asking what life events or interests allowed a person to enter the line of work they are currently in will lead to more interesting answers.
Unfortunately, we aren't all lucky enough to have jobs we are passionate about, but it might still allow the person to highlight their passions and interests, rather than simply saying their job title, yet again. If they are simply there to get a paycheck, a good follow-up question is if they see themselves changing into a different job or industry if they get the opportunity to switch.
4. What Do You Wish People Would Ask You About More Often?
This question may also allow you to know what someone is truly passionate about that might not be discoverable with small talk and pleasantries. Perhaps they have a hobby, cause, or interest that is not going to be an accessible topic with the regular small talk questions people generally ask.
Such an open-ended question can lead to some profound answers and really interesting things you can learn about them. It could also lead to the way a person thinks about the world and whether they have a unique perspective on life and what they think should be valued more highly. This could be a heavy topic, so the next suggestion is a fun one to lighten the mood.
5. What Question Do You Always Want to Ask People, But Don't?
While the last question is about what someone wishes other people would ask them about more, perhaps there is something they would love to find out about but don't. Many topics are considered touchy subjects, but they can often be the most interesting topics that people are very passionate about.
By framing this as an inquiry about the question they would like to ask, you aren't going into the topic itself unless you both choose to. By doing this, you are opening up the possibility of discussing something that people have been conditioned to avoid, and you are doing it in a safe way that shouldn't lead to any offense if the answer is a tough topic like religion or politics.
You could get some real surprises here, so be prepared to hear out what they would love to ask and why they would like to ask about it without judgment, as it is something they avoid doing already. A great way to understand more about this is to ask why they don't ask the question and why they would love to ask it.
6. Do You Love Any Quirky Food Combinations?
A light-hearted question like this can be playful and give you an idea of how serious or playful someone is. If they aren't all that eccentric with their food, the question could be adjusted to ask what food combinations they think are a crime against food, like the commonly controversial pineapple on pizza. This way, you may find out what their favorite things to eat are, which is always great knowledge when trying to create a special connection or even a relationship with someone.
7. Which Book or Movie Has Had the Biggest Impact on Your Life?
By speaking about something that has motivated or deeply moved someone, you can learn so much about their philosophy on life. Some many amazing books and movies could have deeply touched each of us, so learning about something that has fundamentally affected a person's life and perspective is a wonderful way of getting to know who they are, and maybe even finding new materials for your personal growth.
8. What Is Something You Feel People Misunderstand About You?
We all have times when people don't give us the time to truly understand who we are or our intentions. By asking this, you may get some very vulnerable answers. If the person you are trying to get to know really wants to share themselves with you, they will probably tell you about some challenging events in their life, so keep this one for more intimate moments in the time you have together.
Remember to be kind at this point, if they talk about something that makes them feel vulnerable, it's important to be respectful of what they tell you.
9. What Are the Two Biggest Lessons You Have Learned From Previous Relationships?
It might seem counterintuitive to ask about something that may be connected to painful memories, but we all have bad experiences in our lives that we have gained powerful and important lessons. Asking about the biggest lessons they have learned allows them to speak about their personal growth, and you get the opportunity to understand what trials they have overcome in their lives and how they have become stronger.
10. What Makes You Feel Most Alive?
This question is to find out what makes a person light up from inside. It could be anything from a topic of interest, hobby, personal project, family, or pets. Whatever it is, make sure that you appreciate the fact that it brings them light and happiness, even if it isn't something you have any interest in at all. You can respect their interests and passions and make you an interesting person for caring about their interests and emotional needs.
11. What Do You Think Everyone Should Do At Least Once in a Lifetime?
You could get some really surprising answers here, from working as waitstaff to going skydiving. There may be some heartwarming answers like having children or traveling, but whatever the answer, ask why they think it is such an important thing to try and what people can gain from the experience they feel is so valuable.
Let's take the seemingly surprising example of working as waitstaff. They may want people to learn that treating those who serve you with kindness is really important, especially when we have no idea how hard they have worked to provide a service.
This can show great emotional depth and help you understand what your conversation partner values in their friendships. It could also give you great ideas for fun things to do.
12. What Makes You Feel Loved and Appreciated; What Is Your Love Language?
By understanding what makes someone feel adored, you can identify their manner of giving and receiving love. Clear communication about something this important helps build an intimate connection with someone and strengthens a relationship very deeply.
If the person you are getting to know has no idea what their love language is, you can take this fun quiz together to find out which of the five love languages is the strongest. The five languages are categorized as words of love and affirmation, quality time spent together, physical affection and touch, giving and receiving gifts, or acts of service to help out and make life easier.
Whatever topics you love to discuss, remember to be respectful and listen carefully to the answers you get. A great conversationalist will listen not just to respond but to understand what the other person is trying to tell them. If you listen carefully and ask good follow-up questions, you will have held a great conversation that should have allowed you both to get to know each other quite well.
Another tip for preparing yourself to have great conversations is to think deeply about all these topics and how you answer them - what do you think about all these questions, and what are your answers? You should be able to give a good answer to all the questions you want to ask, not just to give an example of what you mean by your questions, but also to show that you have taken the time to get to know yourself well and to be confident in who you are.
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