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20 Questions To Ask & Not To Ask On A First Date

First dates can be quite a stressful experience and trying to find the right things to say or the appropriate topics could be tricky. On the one hand, you want to come off as interesting, funny and why not, sexy, but on the other, you don’t want to make it all about yourself.

Although not easy, knowing what to talk about or what questions to ask on a first date is really important. According to a study conducted by Stanford University, the longer people converse during their first date, the higher are the chances for a second one. Fluid communication can help potential partners focus more on key issues, such as personality traits or common interests and less on superficial aspects like looks. 

If you hope to get past the awkward first date and have a good time that could lead to other pleasant dates and possibly to a relationship, here are 20 useful questions to keep the conversation going.    

  1. What do you like/hate about dating?

This is one of the best questions to ask on a first date, as it allows the other person to share not only their expectations for the date, but also as much as they want to about themselves. This will make them feel comfortable, while giving you the chance to learn something about your date and potentially what you should or should not do.

  1. Where did you grow up?

Discussing your background and childhood can be a smart move indeed, because it is a fast way to get to know one another and it can also point out similarities that might help you bond. 

  1. What is your favorite movie / TV show / book / sport?

Talking about the latest TV series that got you hooked or analyzing your all-time favorite books can help a conversation run smoothly. Since a person’s preferences in various fields can reveal so much about their personality, this topic can be a true compatibility test. 

  1. Have you ever experienced something out of the ordinary?

Finding out an unexpected, incredible fact about the person you are interested in is a fun way to discover who they are. So try to see if they have ever done something wild or extraordinary, like being on TV or going on a safari expedition.

  1. What would you like to learn or wish you were better at?

A good question to ask on a first date that takes the conversation to the next level and allows you to get to know the other person better. Talking about dreams and ambitions could help you determine if there are any sparks between you and your date.

  1. Do you like to travel?

Traveling is a great conversation starter because it enables you to share your experiences, both good and bad and disclose the places you are planning to visit one day. It is also a simple way to look for common passions.

  1. What is your favorite place on Earth?

Closely connected to the previous question, its answer could help you find out a lot about your date, from their favorite vacation destination to what they like to do to unwind. It is a good indicator as well of whether they are rather solitary or a people’s person.

  1. Who are the special people in your life?

One way of learning about someone’s character is to listen to them talk about the people in their life. Thus, you can understand who has had a big impact and help them become the person in front of you.

  1. What is something that truly annoys you?

Finding out early about someone’s pet peeves can give you an insight into their behavior and provides a good opportunity to be open and direct with each other from the start.

  1. What are you proud of?

All modesty aside, this is one of the best questions to ask on a first date, since it shows what your potential partner considers worth working hard for and whether you share the same values.

  1. What is your favorite thing about your career? 

The answer can help you determine how serious and driven your date is and also what are some of their long term goals and ambitions.

  1. What makes you laugh? What are the things you find funny?

Sharing a sense of humor is vital to a relationship. Laughing and having fun can create and tighten a bond between individuals. So you will probably want to spend more time with a person if you find the same things funny.

  1. What do you like to do in your spare time?

Talking about passions and preferred pastimes is perhaps the easiest way to connect with your date and enjoy their company. Moreover, you could find common hobbies and fun ideas for future dates.

  1. What was the most interesting thing you have done in the last year? 

These types of questions are useful to learn about personality traits, see if the other person is spontaneous or not. Plus, it can lead to a pleasant and intriguing conversation.

  1. What are some of your favorite memories? 

Although it might seem a little too personal, going down the memory lane allows you to take a peek at the activities and people your date treasures. As a result, you could get to know them better from the first encounter and decide if you want to meet again.

  1. Are you a morning person or a night owl?

This is really a compatibility question, especially for those who met online and are looking for a long distance relationship. Synchronizing schedules is rather important for remote partners.

  1. What is your favorite holiday?

Despite the apparent banality, this question made the list due to its complexity. It can open the door to so many other topics, such as family, childhood, food preferences, not to mention the sensitive subject of religion.

  1. Do you consider yourself a gourmand?

Since first dates can be more casual than dining out, bringing food into the discussion can be a great idea to ask for a second date. It is a good way to share some of your culinary experiences and exchange thoughts about the best places to eat around the town.

  1. Do you enjoy trying new things?

Pay attention to the response, because two people who share an interest in exciting new adventures could be quite the match.

  1. Would You Rather…? questions

They make for fun icebreaker questions that can be answered by both participants and can de-stress the entire evening. 

Moving on, for a good impression,  you might consider steering clear from the wrong questions to ask on a first date. Topics like money, sex or religion are not ideal when you just met someone.

Here are 20 questions NOT to ask on your first date.

  1. You seem great, why are you still single?

Being single is not necessarily a bad thing. Furthermore, being so rude and skeptical are not exactly flattering features. So just be glad that you have the chance to get to know the amazing person on the other side of the table.

  1. Are you dating anyone else?

It is simply too soon to ask a question that has a deeper and private meaning, concerning your date’s sex life. After all, this isn’t the only thing you’re looking for, is it?

  1. Where do you see our relationship going?

Such a query can make you look desperate, while putting unnecessary pressure on your date. You don’t even know if there is even going to be a second rendezvous.

  1. Do you want to have children?

First dates should progress at a slower pace and on a casual note. Don’t address such an important subject when you’ve known the other person for 10 minutes or so.

  1. How much money do you make?

While talking about your jobs or careers is highly acceptable on a first date, asking about people’s earnings is considered inappropriate and tactless. You could come across as a gold digger.

  1. What do you think of my outfit?

Any question about your appearance puts the other person on the spot and you wouldn’t want either of you to feel uncomfortable during your date.  

  1. How much did that cost?

Noticing and complimenting an item of your potential partner, a shirt or a watch is one thing, but inquiring about their price is completely disrespectful and frivolous. 

  1. How is your relationship with your parents?

This can be a tense subject, particularly for people who have lost their parents or who come from the foster system. In addition, the relationship with their parents is not a barometer for their other relationships.

  1. What Are You?

Using this question to find out a person’s race or ethnicity is a mistake for sure. They will discuss their inheritage on their own terms.

  1. What would you like to do tonight?

Asking questions like this can make you look unprepared, like you haven’t really put any thought into your date or you didn’t take it seriously. And that could spoil your whole evening.

  1. Do You Drink A Lot? Because I Do

You may intend it as a funny comment, but there are slim chances that your date will see it the same way.

  1. Why did your last relationship end?

Previous relationships are a difficult topic, even for senior couples. Moreover, it could still stir up negative feelings, which will ruin the mood for both of you.

  1. What are you looking for in a relationship / partner?

Yet another issue more suited for later on in your possible relationship, it might make things seem forced, like you’re looking to fill a certain role.

  1. What are your deal breakers?

You may want to save some time and check if you think alike, but this can be a tricky and often too direct of a question. 

  1. How many people have you slept with?

This is amongst the most private, intimate information for anyone and it cannot be shared so quickly with a total stranger.

  1. What is your favorite sex position?

Again, a sex inquiry is never appropriate for a first date, no matter the funny or silly tone you might take on.

  1. Do you always eat/drink this much?

It is a tacky, impolite question which achieves nothing, except making the person who asks it look like a cheap, offensive date.

  1. What is the most embarrassing thing that has happened to you?

Try to process a little before sharing any unpleasant stories. Recounting awkward moments from your past may not be the entertainment your date had in mind for that night.

  1. Do you have any health issues I should know about?

Asking for too much, too soon may put the other person in an uncomfortable position. Should you two connect, you will find at the right time if there is something you need to worry about.

  1. What can you tell me about yourself?

This type of approach can be way too general. It is better to ask specifically what you would like to know about your date. Or you could make them feel more at ease if you take the lead.

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