WHAT TO ASK AND WHAT NOT TO ASK ON YOUR FIRST DATE?

Dating is a discovery process and it is all about the conversations. Good conversations take time and attention to build. Sometimes when two people are merely starting to know each other it is difficult to keep a conversation going. You are supposed to have a great conversation with someone you barely know and that’s not easy to do.

For some it is easier to talk to people they don’t know really well while others find it challenging to keep up the small talk style conversations. In general, there isn’t enough common ground covered yet between the two people to have an easy flow. Questions and conversation starters can be good base to rely on when you are dating and finding common ground.

In this post :

• 5 tips for starting and keeping up a conversation with someone new
• 10 questions we don’t advise you to ask on a first date
• 10 questions to ask to reveal some common interests
• Conclusions and Takeaways

You might think that dating is outdated. Texting and apps are the modern form of dating and that is right to some extent. But sooner or later you’ll find yourself face to face with the person you are texting with. No matter how long have you’ve texted for, when you first meet them in person they will feel like someone you don’t really know. Real connection and relationship is created through real conversations, real experiences and face to face meetings.

How to have a good conversation with someone new?

The most important idea for dating is to find common ground and to build connectivity that could grow into a friendship or a relationship. Here are a few basic concepts to keep in mind when engaging in a conversation on a date with a person you don’t know really well:

• You can start establishing common ground and connection by commenting or asking about something in your environment. A common strategy is to talk about the weather but that is a bit old fashioned. A good conversation opener is commenting or asking questions about the place where you are. Have you ever been to this restaurant before? (What is you favorite from the menu? )Why did you choose to meet in this park/ coffeeshop? You could express your opinion first and then ask them whether they agree. I like the atmosphere of this neighborhood, do you find it pleasant too? You can then talk about the city where you are living and how you feel about living there.
• Find small things to build on. You can look for clues in how they are dressed up for example. You can give some compliments about their style. But only if it is real and genuine. The idea is to draw parallels between their likes, interests, activities and experiences and your own. Knowing each other is a process so refrain from wanting to know everything on the first meeting. Let things unfold. It will leave them being hungry for more. Let there be room for next meetings. Keep topics general and easy, like sports, music, movies and pets. There is a list below of 10 easy going conversation starter questions that are pretty safe to use when dating.
• State the obvious commonalities- one thing you share for sure with the other person is the situation you are both in. How you got there is a good topic to start talking about: Did you meet online? Comment something about their profile. Have you been brought together trough friends? Expand on the topic of common friends.
• Avoid asking overly personal questions. People in general are not interested in having deep, big talks with strangers, not even on dates. Most people, including the outgoing ones, do feel uncomfortable sharing their deeper thoughts & feelings with strangers. “Why did your last relationship end?” is one example of those questions that one might not want to go into on a first date. See more questions like this below that are a little too explosive for a first date.
• Commit your attention to the conversation. Be present in the conversation and be willing to listen. People like to talk about themselves and their experiences when they feel safe and appreciated. When you ask something commit yourself to listening while they answer. When you keep looking around while they are answering, or you keep checking your phone while they speak it can make them feel disrespected. Listen when they speak and look in their eyes often. You can lean slightly forward towards the person to signal interest and you can nod occasionally to show that you are on the same page.
• Ask open ended-questions – the best conversation skill you can develop is to ask open ended questions. They are questions that cannot be answered with a simple YES or NO. For example: instead of asking just “Do you like ….” ask also “What you like most about…”. Questions starting with HOW and WHAT typically open the door for the other person to give a more detailed, elaborated and personal answer. Just a small reminder : don’t forget to answer with details when asked an open ended question.

10 Questions Better Not To Ask On A First Date

Dating is not a job interview. Dating is a process and when you are asking people overly personal questions on the first meeting it signals them some kind of lack. It can be lack of trust that there will be a later, better occasion to go into personal details. It can be a fear of loosing time and in this sense a lack of time form your part. It can give them the impression that you are in a hurry.

It is normal that you want to know more about the other person but that conversation flows almost natural when you are on the same vibe. You don’t want to sound like a detective and is quite hard to find the balance of asking the right questions without sounding too interrogative. A general rule of thumb is to stay away from the questions that you don’t feel comfortable answering yet.

The main topics to refrain from on the very first meeting with a new person are religion, politics, money, social status, family, economics and previous relationships. Why? These conversation topics can be sensitive and controversial for many people and can steer the wheel of the discussion into not so good feeling vibes. Reminding people of negatives can ruin their mood and when they start to feel bad because of thoughts about problems and bad memories they can loose their openness, clarity and fun. It is better to stick to positive and general topics.

1. Why and how did your last relationship end?
2. How many people have you dated/slept with since than?
3. How many people have you dated/slept with so far?
4. Why are you still single? Are you single? Are You Seeing Anyone Else?
5. What Are You Looking for In a Relationship? What are your deal breakers?
6. Where Do You See This Relationship Going? Do you want kids?
7. How much money do you make? Are you a success?
8. Do You Own Your House? How much did that house/ car/ watch cost?
9. What are your priorities in life? Do you regularly succeed with your goals?
10. Do you make your bed in the morning? How frequently do you bathe or shower? Are you tidy and organized?

Some of these questions might come up naturally in which case it is ok to ask and answer them. You can feel it when it comes natural to answer and when you have a nod in the stomach before answering. It is Ok not to answer by the way, or to answer really generally. Not all who ask have good intentions. There are unfortunately people ( narcists) out there who ask these questions early on so they can use the information manipulatively in later conversations.

When you really really want to know something more personal you can go with a general question like: What are the most important things I should know about you?

10 Good Conversation Questions for Dating

Questions are great conversation starters and these first-date questions are collected and chosen with the inspiration to support conversations. When you are barely starting to make a connection with a new person it is good to ask some general questions to lift the dialogue up from the ground. Don’t forget to listen and engage with their answer, otherwise asking questions won’t get you anywhere.

Dating-questions are good to remember when conversations run out of topics and you don’t know what to talk about. You can come up with one of these random conversation starter questions below, but if the conversation isn’t taking off and still feels awkward, than just feel free to leave. It is a signal that you aren’t truly connecting with the other person.

People love to talk about themselves, their ideas, aspirations, experiences and discuss their thoughts with people they find attractive & similar to them. You can invite them to talk and encourage them to open up. When your attitude is that of interest and caring the conversation will find it’s natural pathway.

Note: It is a natural impulse and also a common conversation mistake to jump on hooks you are discovering and tell your story instead of really listening and engaging with their story. In case you have a similar experience you can feel the urge to immediately respond with your impressive story but that usually backfires. They will feel ignored instead of impressed by your story. Let them elaborate on their experiences and as you find the hooks try to remember to use them to maintain a natural discussion. Ask deeper questions and give validating comments instead of jumping in with your experiences. It is your advantage that you know that you have a similar, impressive story and when the times right you’ll present it to them for maximum results.

1. Cutest animal? Do you have any pets? /Did you have pets when you were younger? What are/ were their names?
2. Are you more of an indoors or outdoors person? Where do you spend most of your free time/vacation days?
3. If you had to pick sky diving or scuba diving which one would you choose?
4. Are you very active in your free time or do you prefer to relax at home? Is this a busy period for you?
5. Do you prefer to watch movies in the theater or in the comfort of your own home? What’s your favorite genre of movie?
6. Where is the most beautiful place you have been? What’s Your Favorite Place on Earth so far? If you could go anywhere tomorrow , where would you go?
7. What do you do when you hang out with your friends?
8. What trends did you follow when you were younger?
9. What hobbies would you like to get into if you had the time and money?
10. What music artist do you never get tired of? Is there any art or artist you are really into?

Conclusions and Points to Remember

Dating is slowly getting old-school and you might think it is a thing of the past but dating is just a fancy name for having a conversation with someone you barley know. You can establish connection in many ways these days but meeting face to face is the best way still to discover how genuine a person is and whether there is real connection between the two of you.

Conversation questions can be useful in any situation when you are meeting a new person, not just dating. These questions might sound general and shallow but it is better to stay shallow at first and build the relationship up step by step. In this post we presented some methods and a couple of topics to support a natural, developing conversation. Of course, these are just suggestions.

When two people meet it is always a unique and different atmosphere forming between them. When you meet someone you resonate with whatever you ask can seem natural. When you are meeting with someone who doesn’t resonate with you whatever you ask will be awkward. Trust your instincts and know that some people just do not match so it is not about you and it is not about them. There is nothing wrong if you cannot speak with some people, let them pass you by and focus on the ones that resonate with you.

Knowing each other is a process so refrain from wanting to know everything on the first meeting. Let things unfold.

Credits and further readings:

P0-gpointstudio; 17 Tips to Mastering Conversation With New People