According to the R&B singer R. Kelly, “When a woman loves, she loves for real.” This means that women love with all their hearts, unlike men who may love a woman and still have a crush with another one. Women are therefore the most affected when they realize that men they admire do not feel the same towards them. It is therefore important to ask your guy questions that matter in order to determine whether he loves you or if he is the right person to take to the next level if you are already dating. The dilemma among many women is determining the right questions to ask a guy without hurting him or embarrassing oneself. If you are in this situation or you have a friend you want to help, here are 10 most interesting questions to ask a guy you like in order to determine if you he is your suitable match.

10 Best Questions to Ask a Guy On The First Date:

What makes you smile?

This is actually among the first questions to as a guy before you even start dating. This question serves a polite way of letting a guy to know that you are concerned about his happiness. You can also tell from his response what things to avoid and what to do in future in order to make him happy and contented with the relationship. If the guy is made happy by things that you do not like, he is not the right person for you. Remember that every successfully relationship begins with knowing what every partner loves.

What are your favorite hobbies?

This question can help you to determine whether you share some common interests and hobbies with your guy. The question can also help you to know your crush more and know how he likes spending his free time. If he likes sports, this question will help you to know his favorite sporting activity. If you realize that you share some hobbies, it becomes easy for you to invite him in future so that you can have some fun together and you know him even more.

What makes you nervous?

This question serves a polite way of asking your guy what makes him comfortable and as well as what makes him uncomfortable. You can figure out your partner’s strengths and weaknesses depending with how they respond to this question. If you are looking for guy to serve as your protector, you can use this question to tell whether your guy is brave enough to protect you or you are even better than he is.

What is your family like?

Many men are more attracted to women who show concern about their family, and the people they know. This question can also help to know more about the family of your guy without asking sensitive questions. The guy may open and share with you crucial information such as he was brought up in an orphanage or he has a single parent. You can judge from the responses you get in this question who are the closest family members of your guy.

What is your craziest thing that you have ever done in life?

It is good to know the boundaries of your guy and know how far he can go especially if annoyed. However, it is rude to ask your guy as straight questions about their dark past. Asking him the craziest things that he has ever done in life can help you to know if you can keep up with them or if you have done crazier things in life than he has.

What is your favorite romantic activity?

It is worth noting that guys have different approaches to romance than women. It is therefore important to know your guy’s romantic activity in order to know what to do to spice up your relationship. You can also tell whether your crush is the suitable guy for you based on the answers he will give in this question.

Would you like to hang out with me often?

The way your crush answers this question should tell you if he is interested in you or bored already. The question also serves as a polite way of telling a guy that you enjoy his company and you would love to spend more time with him without sounding as if you want to possess him.

Who is your ideal girlfriend?

This question is a polite way of asking your crush whether you are the right girlfriend for him. You can tell your position in his life based on how he answers this question. This question also helps you to know what drives your guy crazy in a woman in order to up your game if you want to keep him. On the other hand, if you are not ready to satisfy his qualities for a girlfriend, then you are not his match.

Would you cuddle with me?

This might sound as a sensitive question but you cannot afford to avoid it, especially if you are looking for a potential future husband. If he answers yes, then you should know that he too has feelings for you. If he says no, then are just a friend to him and there is nothing much between you than a general friendship.

What is your definition of intimate?

If you are already dating, this question will help you to know if your guy is satisfied with your intimacy or not. You can also use a question to tell whether your crush is a decent guy or person who thinks only about sleeping with a woman.


Well, if you are dating or you have a crush, now you know some of the interesting questions to ask a guy. However, it is worth noting that the above questions are not the only ones, but the most interesting among many. Some of the above questions may sound weird when coming from a girl but you cannot avoid asking them if you really want to spice your relationship, know where you stand in a relationship or whether your crush is a suitable match for you. You really need to ask your guy the above questions if you are interested in him and you want a more than a friend relationship.


Anna Perkins is a relationship writer who offers her own forthright opinion over the worlds of dating, romance, relationships , marriage and friendships. She loves cats, traveling, spending time with her son and husband.

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