20 Questions to Ask Someone You’re Dating

Here are some question ideas that you may use when you run out of things to ask the person you’re dating. This article will also explore reasons why it is important to ask these questions, and some tips on how to properly ask questions.

The simplest way to get to know someone we’re dating is to ask questions. However, it is not always easy to know the right questions to ask or the right way to ask them.

To explore this topic, this article will cover the following:

• 20 Questions to ask someone you’re dating
• Why is it important to ask these questions?
• Tips on how to properly ask questions

Let’s get to it!

20 Questions to Ask Someone You’re Dating

Here are some of the questions you might ask the person you are dating, either during your casual online conversation, late-night talks, or first date.

1. How has your week/day been going so far?
2. What genre of music are you into?
3. What film genre are you into?
4. What are your comfort foods?
5. What is your pet peeve?
6. What are your current interests?
7. What are your guilty pleasures?
8. What does it take to make you angry?
9. What does your ideal weekend entail?
10. Where did you go to college (or high school)?
11. Where is the farthest place that you’ve been to?
12. What is the best thing that has ever happened to you so far?
13. What makes you attracted to someone?
14. Where would your perfect date be?
15. What is the most embarrassing thing that you have ever done?
16. How do you see yourself in the near future?
17. What is your greatest achievement so far?
18. What are your personal goals right now?
19. What are you looking for in a relationship?
20. What do you think is the most important aspect of a healthy relationship?

Why Is It Important to Ask Questions Like These?

• To get to know more about each other. One of the most obvious reasons for asking questions is to learn more about one another. In reality, no matter how long we’ve been together, we cannot learn everything there is to know about the person we are dating. Hence, whenever we ask the right questions, we unlock a piece of important information about one another. Also, if we are seeking a long-term relationship, we must remember that love alone is not enough. We need to know the person we are planning to spend the rest of our lives with.
• To foster meaningful conversation. Having a meaningful conversation is an important part of dating, regardless of what stage it is at. Asking the right questions in the right way eventually results in meaningful conversations, which help build a deeper connection between two individuals.

4 Tips on How to Properly Ask Questions

We can be overwhelmed by the sensations and emotions we have whenever we talk to the person we like. Sometimes, it can become overwhelming and prevent us from having a proper conversation or even from asking the right questions.

Here are 4 tips to remember in order to ask the right questions to the person we’re dating.

1. Avoid Closed-Ended Questions

As much as possible, avoid yes-or-no questions because it makes our conversations sound dry and lame. Close-ended questions tend to produce direct and simple answers that don’t need further explanation which is a big no-no during dating. These questions will make the person we are dating bored and eventually, uninterested.

Avoid questions such as,

• Have you traveled before?
• Are you a Marvel fan?
• Do you have a favorite music?

Although we must avoid this type of questions, they can still be useful as introductory questions or questions to ask when starting a new topic of conversation. See the following examples.

• Have you traveled before? Where was the farthest place from home that you’ve been to?
• Are you a marvel fan? Which character resonates with you the most?
• Do you have a favorite music? What is it?

2. Learn to Follow Through

To make the conversation more meaningful and deeper, follow through on your questions, especially on our what, where, and when questions. Note that these wh- questions can be closed-ended questions when they are not followed through.

We can follow through by asking for more information or insight. For example,

You: What film genres are you into?

Them: I’m really into sci-fi lately.

You: What specific movie or movies do you like?

Them: Nothing specific, actually, but I’m a huge fan of the MCU and the Star Wars franchise.

We can still go deeper on this topic by asking them what made them like this specific genre or movie, how they got interested in it, and so on.

3. Know Your Limits

In relation to the second tip, follow through with the questions, but we must also know our limits. Sometimes, the conversation can be so good and interesting that we might ask something too personal, which can make them uncomfortable.

The level of dating we are into can be a huge factor. Normally, if we are still in the getting-to-know stage of dating, it is best to not get too personal with our questions unless there is an agreement between the two parties that it is okay to be personal.

As a general rule, the longer we are dating someone, the more it becomes okay to ask personal questions.

However, we must remember that everyone is still different from one another. Some may be okay with a personal question, while others are not. There may also be people who can tolerate a certain number of personal questions but not all of them.

Similarly, there are individuals who will clearly tell us that they are not comfortable with the question, while others will not. Hence, it is best to keep a sensitive mind and be wary when asking questions.

4. Avoid Sounding Interrogational

We don’t want our conversation to sound interrogative because that will make the person we are talking to uncomfortable. Hence, we must take our time and ask our questions one at a time.

Yes, it is thrilling to know all that information about them, but save something for your next date or conversation.

We may also avoid sounding interrogative by answering our own questions. This strategy will not only make us trustworthy, but it will also make the conversation feel light and two-way.

We may do this strategy in two ways:

1. We can share our own insights first and then ask about theirs, or
2. We can ask them the question first, let them answer, and then share our own insight.

See the respective examples.

Chocolates give me so much comfort every time. How about you, what is your comfort food?

— You

You: What is your comfort food?

Him/Her: Well, I love food in general, but apple pie is always my go-to food. I will never get enough of it. I guess it is my comfort food.

You: Yeah, apple pie is great as well. My comfort food is chocolate. Let’s grab some apple pie and chocolates some time.

Final Thoughts

It is normal to run out of things to start a conversation with the person we are dating. We may experience mental block, be overwhelmed by emotions, or just simply run out of things to say, and that’s okay.

The idea of dating feels good, but it is not always an easy task, especially if someone is just getting into it. However, being with the person you love and care for at the end of it all is something that we must look forward to because it is definitely worth it.

Good luck!

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2023 JC Guiao