July 15, 2024
Chicago 12, Melborne City, USA
Advice Dating advice

10 Questions to ask a guy at the start of a relationship to get to know him better


First things first – there are no wrong answers to these questions, because all of them will be very personal and subjective. The questions are chosen as a means to get to know someone better, not to grade them on their performance. On that note, let’s move on to the questions themselves!

1. What was your very first impression of me?

To be honest, this one is here for the sake of curiosity. But it will also show what a man sees in you, what things or character traits he notices above others and which characteristics he doesn’t notice or doesn’t care about. 

2. What would you prefer: a party in a big crowd or a quiet Saturday evening at home?

While oxytocin and dopamine may be clouding your mind at the start of a new relationship, it is important to find out whether the two of you are actually anything alike. If you prefer to stay in with a book and your partner is all about the party life this should at least be something that you know and are aware of. Discuss this early, since this will help the both of you plan better dates and evenings for each other.

3. What is your guilty pleasure?

This can be a cunning little back door into the secret spaces of his mind! It might let you find out in an innocent manner something that he would otherwise keep private for much longer. And who knows, maybe you will be surprised in a very nice way and will find a whole new reason to like this person even more!

4. What was the best gift you ever received and why?

This will let you find out about what he values more in a gift, be it status, emotions that come with it, who it is from, the significance of the event, etc. Additionally, this will give you a decent idea of what to get him the next time you want to do so 

5. What is your biggest fear?

Good question to become more intimate with your partner. Men are sometimes reluctant to admit any fears or worries, and a relaxed conversation about this in a safe space can mean that you are growing closer.

6. Was there a day in your life that you would like to live through again?

And not in the terms of changing something, but rather to live it again just the way it was in the first place. If the answer is “The day I met you” that might be a clear winner, but you should not be alarmed that he might describe a day from his childhood or of some major personal accomplishment. After all, you have all the power to learn more about him from that and to make sure that his answer will change in the future.

7. Got any pet peeves?

If something minor that you do without giving it a second thought drives your partner crazy, it would be nice to find this out as soon as possible, wouldn’t you agree? After all these things often then get dragged into your first argument as something that has been bothering one of you for a while, but you decided to be polite and kept it quiet.

8. What is your best friend like?

This can get you some insight in what your partner finds appealing in other people, how loyal he is to his friends and how much loyalty they give him back in return. This person might be a frequent guest in your house or at social gatherings, so it would be nice to find out why he or she is so important to your partner.

9. Do you believe that men and women can be friends?

I will have to admit that this one is much more important to me personally than it might be to others, but I think it is a major one. Some people have issues with men and women being friends with each other, and no matter how hard they try they always end up projecting their own preconceptions onto others, and end up judging other friendships through the prism of their own experience.


You might notice that question number 10 is missing from the list. Because I really really think that each and every one of us should add at least one last question that is very personal to them, like I did with number 9. Your experience and your relationship is unique, and while certain things in life quite often end up repeating again and again, you have to put in the effort to make something your own.

Rachel Hall, M.A., completed her education in English at the University of Pennsylvania and received her master’s degree in family therapy from Northern Washington University. She has been actively involved in the treatment of anxiety disorders, depression, OCD, and coping with life changes and traumatic events for both families and individual clients for over a decade. Her areas of expertise include narrative therapy, cognitive behavioral therapy, and therapy for traumatic cases. In addition, Rachel conducts workshops focusing on the psychology of positive thinking and coping skills for both parents and teens. She has also authored numerous articles on the topics of mental health, stress, family dynamics and parenting.

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