7 First date questions tell he's worth pursuing

Are you tired of wasting time on dates with men who are not a good fit for you?

The questions you ask on a first date can be very telling. If you really want to understand what makes a man tick, you will want to ask slightly different questions like the 7 I’ve put together below. Remember to ask these questions subtly and weave them into your conversation naturally. Avoid it being like an interview.

Question 1: How was your weekend?

Begin with this innocent question. On the surface he will think you are interested in his weekend. What you are really listening for is how much detail he goes into. Is he a talker or a one-word man?

Ask yourself will too much detail bore you or do you prefer a talker? Would you rather be with the quiet silent type or would this frustrate you?

Question 2: What did you enjoy most on your weekend?

Here you are listening for what he considers enjoyable and do your interests match.

For example, if he gets really excited about sports, travel, going out with his mates, online games, etc., are they the sort of things you want your man to be interested in? Would you enjoy doing any of those things with him occasionally?

Question 3: What is your least favourite thing to do?

You are really listening to whether his least favourite thing (e.g. shopping, travelling, dinners out, etc.) is your most favourite thing to do. Are you aligned with your interests or are they too different?

Ask him this question before you tell him your interests. If you tell him your interests first, he may just repeat the same things to please you or impress you.

Question 4: What is the most exciting experience you ever had?

As he talks about the exciting experience, watch his face and body language. Does he:
- get really excited, animated and gets in touch with his emotions easily. Do his eyes or face light up? OR
- stay cool and calm and has no change in his facial expressions or body language?

Would you prefer an emotionally connected or emotionally objective partner?

Are you tired of wasting time on dates with men who are not a good fit for you?

Question 5: When were you the happiest on a date?

Pay close attention to this answer as it will tell you how he interacts with you on future dates and in a relationship. If he was happiest when:

  • he was playing with the latest gadgets (e.g. car, technology, etc.) on a date, this man is likely to enjoy his man cave in a relationship.
  • he was out and socialising with the date and they connected with some other people, this man enjoys time with his partner.
  • he was making sure he wasn’t late, all went to plan, etc., this man enjoys processes and being organised in a relationship.

Question 6: What is important to you in a relationship?

This question will determine if he has the same priorities as you do in a relationship. Look for one or two word answers like “friendship”, “fun”, “attraction”, “family”, “time together”, “love”, etc.

Notice if:
- his priorities line up with yours (this means you need to know yours first).
- he takes too long to answer as this could mean he is unsure.

Then ask yourself if you really want to go on another date with someone who does not know what he wants in a relationship.

Question 7: Why are those things important to you in a relationship?

Listen to his replies:

  • Does he reply with negatives e.g. don’t want to be alone; or
  • Does he reply with positives e.g. to enjoy special moments with someone else.

This question will determine if he is a kill joy (focuses on the negatives and problems) or solution focused and positive. Which would you prefer in a partner?

By asking these 7 questions on your first date, they will help you to save time and hone in on which men are worth pursuing on subsequent dates.


Dr. Vesna Grubacevic is an author, speaker, media commentator, the founder and Performance Transformation Expert® with award-winning company, Qt. She is the creator of breakthrough behavioural change techniques, holds a PhD, a BEc and has over 35 years’ business experience. She is passionate about helping people to improve their relationships and confidence. Her Amazon best-selling book, Stop Sabotaging Your Confidence, has also been gifted to Hollywood and Australian award winners, nominees, hosts and celebrities. For more free resources on improving your relationships, please visit

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