Top 45 Questions to Ask a Date


Whether you are just starting to Date or re-entering the Dating scene after a divorce or loss of spouse “What do you talk about?” is often a challenge. You meet a potential date online or at a social venue how do you get the conversation going? Impressions are made within 30 – 60 seconds, you only have a few minutes to see if there is chemistry between you and your date, you want to ask the right questions to see if there is compatibility. What do you talk about to make the most of your conversation?

Below is a list of suggested questions to you can ask, they can range from silly to serious: You don’t have to ask them all on the 1st Date (some might scare them off!), some are more in depth and can wait until the 2nd or 3rd Date. Read over them until you are familiar with them so they don’t sound forced or contrived.

1.What do you do for work?
It is an introductory question. It may reveal the professional status of a person but little about his personality. So move on to another question.
2.Where are you from? This reveals background. It throws better light on the person.
3.What is the one thing about yourself that you would like me to know?
More insight into personality.
4.When was your last relationship and how long did it last? A probing question that will open up the communication.
5.What are you looking for in a relationship? You can both instantly compare whether you match in this area.
6.What do you think is the most important value in a relationship?
7.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.
8.What do you look for in a husband/wife? Try to elicit an honest answer.
9.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.
10.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?
11.What are you most proud about? This reveals the basic values of the person, whether he/she values money or adventure/intellectual pursuits.
12.Is religion important to you? 24×7 living together means understanding on certain basic issues like religious beliefs.
13.Do you follow politics? Are you a Democrat or a Republican?
You can spar on your political affiliations.
14.Do you believe in love at first sight? You can decide whether he/she is a romantic person or not.
15.What is your most treasured possession and why? What a person is sentimental about reveals a great deal about his personality. Is it his bike or a locket presented by a sister?
16.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?
17.Which is your favorite book/movie? Both of you can discuss why you like a book or a movie – throws further in sight into personality.
18.Which is the last book you read? A conversation starter.
19.Which is the one job in the world that you would love to do?
Throws light on likes and dislikes.
20.Which is your favorite music and your favorite singer/band?
Do you share musical tastes?
21.Do you like animals/keep pets? Are you going to clash on this issue – one an animal hater, the other a pet lover?
22.How do you spend your spare time? This is important, as it will really help if both love to do the same things in spare time.
23.Where do you see yourself in five years time? Watch out if he has no definite goals for the future and is in a rut. A positive mark for her if she has her life and career planned out positively.
24.If you were an animal in the wild, what would you be?
Silly, amusing question to get the laughs.
25.Do you believe a cup is half empty or half full? Are you an optimist or a pessimist?
26.If you could travel back through time, what single mistake would you correct in life. What are the deepest regrets of a person?
27.You have got six months to live, what will you do first?
Insight into personality.
28.Is sexual compatibility important to you? Do opinions match?
29.Who was your hero, as a child? Insight into personality.
30.If you won a lottery, how would you spend your millions?
Amusing question just for laughs.
31.Which was the first crush you ever had? Reminiscing sentiments.
32.What makes you laugh/cry? Really important and throws light on personality.
33.If you have friends coming over, what would you cook?
34.Describe your perfect holiday. One thinks frozen Alaska, the other sunny Australia.
35.Which T.V. program would you never miss? Do your tastes match?
36.What is the last CD you bought?
37.Are you a morning person or a night person? Will you ever spend common time?
38.Would you like to climb a mountain or trek across a desert?
Will you ever agree on holidays?
39.What adjective would a close friend use to describe you?
Friendly or idiotic.
40.If you could live anywhere in the world, where would it be?
41.Into which personality�s shoes would you like to step for a day?
Says a lot about your taste.
42.Who is you favorite actor/actress/celebrity and why?
43.Who is your favorite sportsperson?
44.What is your favorite sporting activity?
45.Which is your favorite genre of movies – comedy/thriller/action?

Thank you to the guys at for sharing their questions. Remember these questions are suggestions, feel free to change them to suit your interests and personality. Most of all – take the time to LISTEN to the replies and ANSWER their questions. If any REPLIES send up RED FLAGS or the hair on the back of your neck stands up TRUST your instinct. Employers do pre-employment background checks, why shouldn’t you check out your Date? ( LADIES make sure you meet that 1st Date at a public place, don’t have him pick you up at your home! You wouldn’t invite a door-to-door salesman into your home would you? Men don’t be offended the ladies are just being cautious, there are a few weirdo’s out there.

I am thinking of turning these questions into a pocket size game like Trivial Pursuit for Dating. Would love your comments.

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