Awkward silence is never sexy. Here are the questions to ask on a first date that will give you pretty good odds of securing a second one. But remember, keep it lighthearted and natural—last she checked, she was on a date, not at an interrogation.
17 Questions To Ask On A First Date And Why You Should Ask Them
1. Who Are The Most Important People In Your Life?
This question is definitely one of the most insightful questions to ask on a first date. Your date will most likely answer immediately with, “My parents” or “My siblings” or “My best friend.” This gives you a much better understanding of the people she values most. It also tells you whether she is close to her family or not and allows you to assess her ability to build close relationships.
Follow up with: “What are your fondest memories of them?” “How long have you known them?” “What are some of the things you guys did together?”
2. What Makes You Laugh?
Learning how to make her laugh is an essential part of any relationship. Multiple studies have shown that most women look for a partner with a good sense of humor. They want a partner who can bring lightness to a relationship. Knowing the things that make her laugh tells you a lot about her personality. Subconsciously, she will relate the times you spend together with levity.
Follow up with: Try a funny joke or a witty comment that suits her answer when she asks you this question back.
3. Where Is “Home” For You?
This is one of the more intimate and personal questions to ask on a first date. Knowing where “home” is for her is a lot different from simply knowing where she lives. Asking her where “home” is tells you about where her heart is tied to and the kinds of things she loves doing there.
Follow up with: “Where are you from originally?” “How long were you there for?” “Do you still talk to the people you grew up with?”
4. Do You Like to Read Reviews or Do You Follow Your Gut?
Asking this question might come as a surprise for her, but it is definitely one of the best questions to ask on a first date. It can tell you a lot about your similarities and differences, such as in decision-making. Does she read the reviews first before watching a movie? Or will she watch it regardless of what people say?
Follow up with: Regardless of her response, try asking her for a quick spontaneous trip somewhere near that you think she will enjoy.
5. What Is Your Biggest Dream?
Knowing the ambitions of your partner is a great way to gauge your compatibility. A person’s goals are most likely one of the central parts of their lives. Whether it be focusing on a career, traveling, or even artistic expression, knowing her dreams gives you an idea if your lives are aligned or heading in different directions. It is one of the most significant questions to ask on a first date.
Follow up with: “What made you want to pursue that dream?” “When do you want to achieve it?” “What motivates you to pursue it?”
6. How Do You Spend Your Weekends?
Knowing what she does during her free time is a good question to ask on a first date. If she spends her weekends working, she might either be career-oriented or a workaholic. If she spends them teaching kids at the local library, then you know she is somewhat family-oriented and kid-loving. Knowing how she prioritizes her time says a lot about what she’s about.
Follow up with: Ask her if she would like to do the opposite. If she likes going out, try asking her to stay in and maybe cook dinner and watch a movie. If she prefers to stay in, ask her to go out with you someplace under the radar for a unique date.
7. Where and with Whom Did You Grow Up? What Was Your Childhood Like?
Psychologists say that a stable and satisfying childhood is one of the most reliable gauges of someone’s emotional health in adulthood. While this does not necessarily mean that you should run for the hills at the mention of family problems, it is still one of the best questions to ask on a first date. At the very least, it gives you an insight into her family background. It also lets you see if she is aware of those problems and if she tries to do something about them.
Follow up with: Ask her if she is still close with her family. Get to know what her childhood was like and try asking her how she thinks it shaped her into the person she is today.
8. What Are You Most Passionate About?
This is one of the most important questions to ask on a first date. This allows you to see and understand what she might really be into. Do you have the same passions? Do your passions complement one another’s? Asking this question allows you to see what things are valuable to her.
Follow up with: Get to know what made her interested in that passion. Does she actively pursue it? What are her plans about it for the future?
9. Where Is Your “Special Place?”
Whether it is the local coffee shop, or that bench with that view at the park, or even a different city, this question is one that will let you see your partner’s tastes and temperament. Try to understand where her so-called “happy place” is and maybe ask her why.
Follow up with: “Is there a special event that happened there?” “What made that place so special?” “I’d like to see that someday, maybe you could bring me!”
10. If You Were in a Movie or a Television Series, Where Would You Like to Live?
One of the funny questions to ask on a first date, this should get the conversation rolling on a lighter note. Debate with her and give your opinion and maybe tease her a little about what she said. Again, just keep the conversation light.
Follow up with: Tell her your own movie or television series setting you would like to live in. Ask her why she wants to live there. Keep the subject light and playful.
11. What Are The Things On Your Bucket List?
Bucket lists have always been known to bring about a lengthy conversation. Asking her about this keeps the conversation light, gives you a lot of insight into her personality and provides you an opportunity to be the person she shares her dreams and interests with.
Follow up with: Suggest crazy things to include in the list. Ask her why she wants to do those on her list and when she wants to complete them.
12. What Are Your Guilty Pleasures?
Give your conversation a surprise twist with this one, as you try getting her to share guilty pleasures with you. This is not only one of the funnier questions to ask on a first date, but also it is an insightful one as it lets you gauge how comfortable she is with you. You might be surprised at what you hear.
Follow up with: Share your own guilty pleasures. This is supposed to be a light and funny conversation topic so try to make her laugh.
13. What Is The Possession You Value Most?
Is it a photograph? Maybe a tiny trinket from a place she went to? She might even surprise you with a classic car! Asking this tells you a lot about your date’s passions and priorities. Not only is it an interesting topic, but it also tells you a lot about what she is into.
Follow up with: “Did you inherit this from someone?” “What makes it valuable?”
14. Who Is The Most Fascinating Person You Know?
An important aspect of every relationship is getting to know the people in your partner’s life. This is one of the more important questions to ask on a first date because it does just that. Hearing her talk about other people also gives you an idea about the kind of person she is, perhaps even more than asking her questions about herself directly.
Follow up with: Ask her what makes that person fascinating. Try getting to know more about that person and what they mean to her.
15. What Is The Most Challenging Or Scariest Thing You Have Ever Done?
This might seem like a job interview question at first, but it can actually say a lot. Knowing the kinds of hardships your date has gone through can help give you an idea of how she handles them. Challenges are a big part of every person’s life. Knowing those gives you an idea of why she is who she is today.
Follow up with: “How did you overcome it?” “More importantly, what made you decide to face that challenge and get through it?”
16. What Do You Do For Work?
Understanding what your date does for work can tell you a lot about her. More than that, it gives you an idea about how much free time she has. Ask for details about her job. Does she work on a regular schedule? Is she on-call?
Follow up with: “Do you enjoy your work?” “Are you planning to stay there long-term?” “Do you want to build a career there or are you still looking for other opportunities?”
17. What Kind Of Music / Books Do You Like?
This is one of the lighter questions to ask on a first date. While it may be light, it gives you an idea about her likes and dislikes. Knowing the kind of music she is into could help you choose a playlist as you drive her back home. Books can help you understand whether she reads for entertainment or for learning. Asking this question gives you a lot of angles to work with and keep a conversation going.
Follow up with: “Are you open to trying out new music or reading books of a different genre?” Ask her these questions and try to find music or books that you know she might like.
To know more about date ideas, watch this video from alpha m:
Every good gentleman knows that a first date is all about making a good impression. Getting a good haircut and wearing shoes that match your outfit are only the first steps. If you truly want to impress and make a solid connection, these questions to ask on a first date can help you get things off on a good start.
Are there other questions to ask that you think would help other guys? Share them with us in the comments section below!
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