20 Great First Date Questions

Posted by in understanding men over 40 | 3 comments

Are you stumped as to how to have a good conversation on a first date? My clients asked for some conversation starters, so here’s a list of great first date questions that I adapted from a site called futurescopes.com. Each question will elicit a response that can be helpful in getting to know someone on a deeper level. This information will help you decide if you even want to go on a second date.

20 Great First Date Questions 

1) Where are you from? (This reveals background and throws some light on the person’s history.)

2) What is one thing about yourself that you would like me to know? (More insight into personality and what lies beneath the surface).

3) When was your last relationship and how long did it last? (This will open up communication about how commitment-oriented this person is.)

4) What are you looking for in a relationship? (You can both instantly compare whether you match in this area.)

5) What do you think is the most important value in a relationship? (Choosing the most important value sheds light on this person’s inner workings)

6) Do you want to marry or have you ever been married? (This is important, as it will reveal if both are moving in the same direction – towards or away from marriage.)

7) What’s one thing about you that would surprise me? (You might get a fun response, and be shocked by what you learn!)

8) Do you want/do you have any children? (An important question if you are looking for a long-term relationship and your partner is not.)

9) What do you do for fun? (This will throw light on whether your leisure activities match. Are you a bookworm and she an outdoorsy person?)

10) What are you most proud of? (This reveals the basic values of the person, for example – whether he/she values money or adventure/ intellectual pursuits.)

11) Is religion important to you? (24/7 living together means understanding and compatibility on certain basic issues like religious beliefs.)

12) Do you follow politics? Are you a Democrat or a Republican? (You can spar on your political affiliations. Or not…)

13) Do you believe in love at first sight? (You can decide whether he/she is a romantic person. A realist? Someone with their head in the clouds?)

14) What is your most treasured possession and why? (What a person is sentimental about reveals a great deal about his/her personality. Is it a bike or a locket presented by a great friend?)

15) What is your favorite month of the year and why? (Does he like to sweat it out in summer activities or curl up like a cat in winter? Seasonal compatibility can be an important factor in sharing activities.)

16) Which is your favorite book/movie? (Both of you can discuss why you like a book or a movie – throws further insight into personality.)

17) What is the last trip you took? (A conversation starter. How much does he/she travel? Like adventure?)

18) Which is the one job in the world that you would love to do? (Throws light on likes and dislikes. Is this person doing anything close to that job? Are they happy at work or not?)

19) Which is your favorite music and your favorite singer/band? (Do you share musical tastes?)

20) Do you like animals/keep pets? (Are you going to clash on this issue – one an animal hater, the other a pet lover?)
Can you think of another great question to ask on a date? Please share it here.



  1. I find that talking about professional interests can be stimulating for both men and women, especially if they feel proud of their accomplishments.

  2. Hi Sandy. I saw your comment over at Passion101.com about the “divorce expo” and came over to visit. You have a wonderful site here! I love the way it’s laid out and your home page gets right to it!

    On this post on 20 Great Questions to Ask on a First Date: did you mean to ask all of these questions on the first date?

  3. Thanks for your kind words about my website!

    As for the 20 questions, they are prompts to get a conversation going, not meant to be used all at once to interview your date!

    I would suggest pulling one or two juicy ones that appeal to you while on a first date.

    Thanks again for stopping by. Check out my new webinar offer on the side bar. Please sign up for more info.

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