First Date Questions That Should Be Avoided

Dear Sybersue YouTube

Today on Dear Sybersue I discuss, First Date Questions That Should Be Avoided.

This topic can be controversial as people view 1st dates quite differently.

Some men and women want to get the tough questions out of the way right away to see if the person they are dating fits well with what is on their “expectations” checklist. This can end up feeling like an intense and very uncomfortable interview!

Very few people are OK answering numerous personal questions with someone they just met. It automatically puts them on guard and changes up the dynamics of the date. The atmosphere becomes more clinical rather than a relaxed and easy-going environment.

We all want to feel safe on a date, so trusting someone with this private information isn’t something most people want to openly give out. Not only is it none of their business this early on, but it also is not the best etiquette to expect anyone to engage in this type of discussion.

The first date should be all about fun and learning small things about each other. The interview-style question line comes across as a little arrogant and controlling, which does not leave anyone feeling connected. It actually repels people away and closes them off, and it’s really not an attractive quality to be so aggressive when you are on a first date.

You should always be on your best behavior because as I have said in other posts, “first impressions make or break a second date.

Dating questions are not a one-size-fits-all scenario.

Treat each date individually and talk to them accordingly. You will often know some details about your date from their online profile or from a few texts that you may have shared previously. Use that information to set up your first encounter or as a conversation starter when you do meet up. It is wonderful when you both pay attention to what has already been said and implement those little things into making the first few dates enjoyable.

Refrain from asking too many personal questions, especially on a sexual level. No one wants to feel like they are being interrogated. You need to see if you even like each other first before you share too many intimate details about your life. Be patient and take things slow, even if you are really drawn to them.

Pexels Photo by Vlada Karpovich

Your questions should be creative and not textbook boring or intrusive. Asking someone why they are still single, why they are divorced, or how many people they have slept with is not an acceptable conversation and is a big turn-off. The first date shouldn’t be all about checking off the perfection boxes on your soulmate checklist. If you go into every new situation with high maintenance expectations, you will sabotage any chance you have of meeting your special person. Remember, they are critiquing you as well!

Get into a light-hearted conversation and talk about your hobbies, sporting activities, and what you like to do during your social/personal time. This will keep the discussion flowing and the focus in a less serious mode. It will also offer up some future dating venue ideas should you both decide to see each other again. Rigid questions will shut down the connection quickly, so keep things fun. A little humor is always a good thing as well! That was always high on my own dating list. I loved it when someone made me laugh!

If you find your date is a little shy or nervous, take the pressure off them.

Rather than sitting right across from your date, suggest taking a walk together. It is easier for some people to converse this way rather than having to stare directly into your face. Stay away from asking too many questions in any form. Discuss a funny story about something that recently happened to you, or talk about a vacation you have been on or where you would like to go on in the future. It is also very important to discuss the things you both have in common, which will help make your date feel comfortable and included in the discussion.

Be playful, but be aware of their body language and comfort level. Not everyone is experienced when it comes to dating, so pay close attention to their reaction and how receptive they are towards you. It’s not difficult to sense when someone is feeling a little nervous, but if you are feeling a one-sided connection throughout the date, then you may not be on the same page.

Pay attention to how they treat you on the date.

  • Were they on time?
  • Did they contact you to confirm the date beforehand?
  • Did they offer details as to what the plans were for your date?
  • Were they attentive to you and made sure you felt comfortable?
  • Was the conversation reciprocated and interesting?
  • Were they respectful to you in all areas?

If things go well on your first encounter, I always recommend texting them soon after the date, telling them that you enjoyed your time with them. Planning another date is also a great idea because it doesn’t leave any questions. Game playing is such a problem with dating today, and if you felt a connection with someone, tell them.

It is so much better to find out early if the feelings were reciprocated than to hang around waiting to see if you will get together again. If you are thoughtful, sincere, and true to your authentic self on every date, it will bring you closer to finding the special partner you are looking forward to sharing your life with. You will always feel good about the way you handled things and walk away with your head held high even if things don’t work out for the two of you.

The old cliché, “treat others how you want to be treated” is such a true statement when it comes to dating anyone today. Be real, be you, and give people a chance by taking a little time to get to know them. If there isn’t a connection, that is OK. You will always learn more about yourself with each dating scenario you have. That is a good thing and a part of life that keeps us all evolving into an even better version of ourselves.

Thank you so much for stopping by Dear Sybersue! Please click on the video above to hear more about what I have to say on this topic.

Sybersue xo <3

This image has an empty alt attribute; its file name is dear_sybersue__caricature01-2.png

Private Dating Relationship Coaching With Sybersue – Please get in touch with me @ and message me there to set up a video call or voice call appointment within 24 hours. Thank you!

Susan McCord @ Dear Sybersue YouTubeDear Sybersue Facebook

Dear Sybersue Blogs & Advice ColumnDear Sybersue Instagram

Dear Sybersue Coaching Services

Thank you for visiting Sybersue! Your comments and topic ideas are always appreciated!