27 Personal Questions to Ask a Guy on Your Next Date

Questions to take your connection with him to the next level

By Fred S.
27 Personal Questions to Ask a Guy on Your Next Date

In this article, we’ll go over 27 questions that any woman should ask her counterpart at the beginning of a relationship. There’s no guarantee that you’ll like every answer he delivers, but you’ll be getting to know a whole lot about his character. Let’s get started!

27 Questions To Ask A Guy

1. What’s your personal aim?

This is probably the most important question you can ask a guy on a first date. It lets you know about how big he thinks, and how driven he is. A person’s goals tell you what they are in their life, and what they aspire to be – this is an important detail about their personality!

2. What type of childhood did you have?

It’s a fun question and can lead to some funny stories in the answer. Not only does it serve as a great ice-breaker, but also gives you a peek into how he grew up. Knowing that lets you understand his likes and dislikes better, and brings more context behind the way he is.

3. Do you have any insecurities? If so, what are they about?

Asking someone what they’re insecure about might sound like too direct of a question to ask in the beginning, but the delivery can make it lighter. You can start by letting him know what you feel insecure about, and then ask about his side. At critical moments, knowing this fact about him can allow you to deal with the situation better.

4. What are your expectations from a romantic relationship?

If both of you are asking questions to get to know each other, feel free to slide this one in! It’s good to clarify each other’s general expectation from a romantic relationship. Not all of us have the same idea about them, and it’s good to make sure you’re both on the same page.

5. How far in the future do you want to become a father?

Some couples are too afraid to touch this discussion, even months into their relationship. Later on, when one of the partners expresses their desire to have kids, the other one is shocked and distressed. By asking this question in a casual way, you’d be making a lot of things clear.

6. What do you find the most attractive in a girl?

We all have a unique and ideal ‘type’ of the person we’d prefer as our partner. It’s not about physical attraction or traits about someone’s face or body, but about their views, likes, and dislikes too. It’s a fun way to find out what they’re into.

7. What expectations do you have of yourself?

Again, this is the type of question that gives you high insight into someone’s personality. Their answer will show you how much they value themselves, and how self-confident they are. He’ll probably expect much of the same from you as he does from himself, which makes this a clever one to ask.

8. What are your professional goals?

Asking someone what they’re aiming to achieve with their career tells you about their aspirations and drive. If you’re looking for someone who’s truly passionate about what they do, this question is a must!

9. What main thing(s) do you expect from a partner?

What is it that he needs and expects from a romantic partner the most? What’s the most important thing a girlfriend, fiancé, or wife could ever bring into his life? Match his answer with what you’re willing to bring to the table, and see if there’s enough similarity.

10. What are your friends and family like?

When you commit to a relationship with somebody, you also commit to spending time with their family and friends later on. It’s important to find out what they’re like, what they do, and what type of relationship he shares with them. It’s a simple question that shows him you care about his loved ones!

11. If you won a million dollars, what would you do?

Any question that gives you hint about a man’s priorities, is a great one to ask on the first date. Not only will he reveal what’s important to him, but also reveal his hobbies, interests, and dreams. From his answer, you can also tell how smart he is with his money!

12. What’s the worst thing you’ve ever done?

Here’s one to lighten the mood! You’ll probably start him up on a funny little story with this question, while also finding out some of his values. You get to see his sense of rights and wrongs, which is a core component of someone’s personality.

13. What’s your ideal place to live?

With this question, you get to determine whether you’re sitting with an urban guy or not. If the answer revolves around a certain metropolis, he probably enjoys a fast-paced lifestyle and likes the night time. If his answer has to do with a suburban house with a lush green garden, he probably wants a pet and children. It’s a good question to ask a guy on a date!  

14. How is it working for (his place of employment)?

If he has told you where he works, ask him how it is. See if he enjoys the job or is just doing it to survive. His answer will shed light on his career expectations, and what he’s putting up with right now.

15. What sports are you into?

It’s hard to find boys who aren’t into some sort of sports. They either play one enthusiastically or at least watch it. Ask him about the one he’s interested in, and he’ll be stoked to talk about it!

16. Describe yourself with one word.

Studies suggest that people who use simple, short words to answer this question are skilled and fast. But even if he takes a longer time, and answers with a compound word, he might have never thought about this. Either way, it’s an excellent question to ask a guy on a first date!

17. What is your favorite food?

It’s good to keep the conversation going with easy-going, harmless questions. Find out what he likes to eat, and if you’re lucky, you’ll find stuff in common in this area!

18. What is your favorite character from childhood?

His favorite character will tell you a lot about the traits he looks up to in a person. Pay close attention to the character(s) he mentions, and what he specifically likes about them.  

19. What kind of animal do you love the most?

If you’re an animal enthusiast, then you probably look for the same energy in your ideal partner. His answer can let you know whether your future holds a bunch of cuddly puppies together, or arguments over whether or not to get them.

20. Would you rather choose fishing or hiking?

People who tend to be calmer and focused would normally choose fishing over hiking. These people can spend hours and hours working without getting bored. More adventurous types of men would choose hiking though. This makes it a good question to ask a guy on a first date.

21. Which social media platform do you use the most?

Ask him where he spends most of his time online. It’s a casual question that just keeps the conversation going, while also letting you understand his choice better.

22. What’s on your bucket list?

Ask about what they plan on experiencing in their future. Is it sky diving? Is it scuba diving? Are they brave enough to try bungee jumping? Asking about these details can help you a lot in looking for common factors between the two of you.

23. What kind of music do you like?

For many people, sharing a taste in music is enough to start liking each other, as ridiculous as that may be. Music taste means a lot to people, so remember to be respectful of their choice.

24. What is your favorite movie ever?

This question accomplishes the same objective as the favorite movie character one. It provides you a glance at their taste and shows you what they look for in a movie.

25. Do you believe in God?

It may seem too deep to ask on the first date, but given the right circumstances, it can be asked casually. See if their answer is in line with your own beliefs because this one’s important.

26. Is the physical appearance of girls the most important?

See where they rank a woman’s physical appearance in their priorities. Most men who are being honest would definitely express its importance – after all, you don’t fall in love with someone’s personality at first sight.

27. What is the happiest event of your life?

This question gives him a chance to recall the best day ever. The story he tells you will definitely bring laughs to the table because someone’s happiest event will always be associated with smiles and positive energy. It’s a great question to ask on your first date!

Related Article: 50 Funny Conversation Starters For The First Date
50 Funny Conversation Starters For The First Date

Dating can be nerve-wracking. What are you supposed to say? Here is a list of 50 funny conversation starters to guarantee a second date.


We’ve all heard the saying about the best way to a man’s heart is the stomach, but what about his brain? Penetrating into a guy’s mind isn’t easy, and it requires loads of technical tactics. Women are known to be smart when it comes to all this, but it all only becomes possible by asking the right questions. A question is one’s strongest tool to get direct information about someone’s personality, thoughts, outlook, and perspectives. The 27 question ideas in this article will surely help you out in that regard. All the best!