Last Updated on September 29, 2020
To most ladies, a picture-perfect date is one that takes place in a spectacular setting, complete with delectable foods, refreshing breeze, and serenading beats. Much as these are important, they certainly won’t make the experience enthralling if the conversation takes on a boring tangent. And the surest way to wind up with a dull conversation on a date is to ask the usual questions.
Admittedly, you’ll naturally want to begin with basic questions that allow your man to open up so that you can get to know him better. But after that, you should raise the stakes a little higher by asking questions that will enable you to establish whether he’s interested in you or not.
Remember that sometimes, you already know the answer. You just want to hear it from the horse’s mouth as you read his body language to be sure he means what he says.
Table of Contents
The following are some of the top questions you might consider asking your man on a date.
1. Tell me more about yourself
One of the most classic questions to ask a guy on a date. In their answers, most men will include details about their full names, family, education background, and employment history.
2. Where do you come from?
You want to know whether you’ll be flying or traveling by road to meet his in-laws. Who knows – he might not even be from out of town.
3. What do you do?
A direct question that’s intended to find out if he’s employed or not.
4. What does a typical day look like for you?
If you find ‘what do you do’ a bit direct and offensive, this would be a politer question to ask. He will enumerate all the things he does on an average day and from there, you can establish whether he’s working or not.
5. What was your childhood like?
If he had a violent upbringing, expect that to reflect heavily in the relationship.
6. What’s the most stupid habit you had as a child?
It’s important to know what he was notorious for and whether he has outgrown the habit or not. Remember, ‘old habits die hard.’
7. What are your personal goals?
It’s now time to get deeper and uncover what his personal life goals are.
8. What are your professional goals?
This question will help you to establish whether he has any long-term career goals. Is he seeking promotion at work, to establish a business, or enrol for a master’s degree program?
9. Where do you see yourself in 10 years?
Another excellent question to gauge how visionary your man is.
10. What are your worst insecurities?
A man’s insecurities are some of his deepest secrets that he would rather let you find them out by yourself. The earlier you know what they are, the better equipped you’ll be in the event you finally have to deal with them.
11. How many relationships have you been in?
This is your perfect chance to establish if he’s a cheater, serial monogamist, or just unlucky in love. Generally, the number should correspond to his adult age. Although not always the rule of thumb, a 30-year old man probably began serious dating at 20. For ten years, he’s likely to have been in a maximum of three serious relationships.
12. How did your last relationship end?
Look out for justifiable reasons, such as his ex-girlfriend cheating on him or the pair coming from conflicting cultural backgrounds.
13. How long have you been single?
Beware of a man whose last relationship ended a month or two ago but is already seriously chasing you. Yours may be a classic case of a rebound relationship.
14. When was the last time you got laid?
The question may come across as a bit direct and impolite. But if he’s been single for a year but got laid just a month ago, doesn’t that reflect negatively on his sexual activity?
15. What do you expect out of this relationship?
Don’t be contented with basic answers like ‘love’, ‘trust’, and ‘fidelity’. Dig deeper.
16. What qualities are you looking for in a woman?
Not to be confused with the above question, the answers to this question should focus on the specific characters he’s looking for in a woman. Does he prefer a quiet or talkative woman, a homemaker or career woman, etc.?
17. Would you want to have children someday?
A very important question right there. Does he want children right about now or in 10 years? Maybe he doesn’t want children at all. The sooner you find out, the better. And while you’re at it, also inquire about the number of children he might wish to have. Some men prefer one or two children; others prefer them to come as long as they can.
18. Who are your friends?
As the saying goes, ‘you’ll tell the character of a man by looking at his closest friends.’
19. What’s your favorite animal?
Many men have pet peeves. Instead of asking what their pet peeves are, this question will offer you more insights into that.
20. What are your phobias?
If he’s afraid of the dark, know that you’ll always be the first to walk through the door whenever the two of you come home late from a picnic.
21. What’s your favorite meal?
‘The way to a man is through his stomach.’ So, do yourself a favor and know the foods that he loves the most.
22. What’s your favorite city?
This question is intended to uncover the traveler in him. If he loves to travel, he will definitely throw around some fancy and exotic names. If he mumbles to answer the question, then he’s definitely not been bitten by the wanderlust bug.
23. What are your favorite hangout joints?
Isn’t it great to know where you’ll go fetch him if he stays out late?
24. Who is your idol?
The answer will clue you in on what his hobbies and interests are. A Leonardo DiCaprio fan is definitely a movie lover, a Chris Brown fan music-lover, a Lionel Messy fan a soccer lover, etc.
25. What do you make of gender equality?
Some men are renowned chauvinists. This question will help you know what he feels about women and their roles in a relationship.
26. What are your political/religious views?
You want the man to have some degree of political and religious awareness. But the last thing you want in your life is a political sycophant or a religious bigot.
27. What was your closest close call?
This question is appropriate when you want your man to narrate a great memorable story.
28. Have you ever been handcuffed before?
An excellent way to establish if he has any criminal records. Better yet, you can find out about his bedroom kinks.
29. If offered a chance, what would you do to change the world?
If you want to know if your man has a higher calling, this is the question to ask. He could be passionate about issues like environmental conservation, gender equality, or unemployment.
30. What’s your worst purchase ever?
A perfect way to gauge his money sense.
Conclusion
Remember that each date is a unique experience. So, the questions that you ask must relate to the experience. For instance, you wouldn’t want to ask your man what he feels about having children if he already has children from previous relationships. That would sound a bit subjective. The convention is to shun the obvious and only go for questions that help you uncover new information about him.