10 Flirtatious And Fun Questions To Ask Your New Boyfriend

Did you just start dating this amazing guy that you might be currently obsessed with? Congrats dear!
Do you want to know some cute and flirtatious questions that you can ask him when both of you are hanging out or on a date?

These are the most flirtatious and fun questions for you to ask him to keep the conversation fun and interesting. As you also get to know more about him.

Nothing is more fun than having a well flowing conversation with cute little questions that help you know more about your new partner.

Check out these fun and flirtatious questions to ask your new boyfriend on your next date.

These questions will work better for you if they are asked physically, so it’s better to wait until you guys hang out together to pop up these questions, rather than texting him the questions.

Here are the questions:

1: What did you think about me when you first saw me?

This question will make you understand what his first impression of you was. Was he like ” this is the girl I want to spend the rest of my life with” or was he like ” oh God! Now what?”

This type of question will trigger him to think more than what you just asked him. The answer for this question will determine how the future of the relationship is likely to be.

Also Read: how to tel if your boyfriend truly loves you ( supported by psychology)

For the record, guys seem to get attracted to girls the very first time they see them. But some guys might not be attracted to you the first time they see you, but after spending a couple of days with you, they might start developing feelings for you.

So this question will definitely help you figure his first impression of you.

2: What is your most embarrassing moment? 

Some people have worse embarrassing moments that they may not want to share yet.
But if he’s comfortable with sharing his most embarrassing moment with you, go for it.

You will learn a lot from your new boyfriend from his answer of this question.

If he doesn’t want to share his most embarrassing moment with you just yet, don’t take it personal, trust has to be gained for people to put out other subjects about their lives. Just assume it and move on to the next question.

3: What do you consider your greatest accomplishment? 

Guys have huge dreams and goals.
Find out what he considers his greatest accomplishment by asking him this question.

You will be able to learn a lot about his, dreams, goals and future plans with how he answers the question.

This question will help you find out his values in life, and what he treasures the most. After all, you are just getting to know him at a personal level so take every detail into consideration.

4: Who was your first crush? 

Now we are talking..

A guy’s first crush is unforgettable, you can trust on that.

Guys don’t forget the girl they had a crush on easily, your boyfriend too, he probably remembers her.

By asking about his first crush, you will know what he likes in women, generally.
The first crush of a guy can also determine her future or dream girl. ( although people change and so do their perspectives ). This will help your relationship in general as you will have an idea of what he finds attractive in women and what he doesn’t.

5: Did you like school/Do you like school?

This question depends on what level you guys are in life, for example, you can ask him if he ever liked school only if, he is already done with school.
Or ask him if he currently likes school, only if he still goes to school. Not the other way around.

People are not the same, some people thrive in a classroom environment, while others favor more active, hands-on learning. Asking him this question will help you find out which way your boyfriend leans with this question. If you are both on the same page, even better. For example if you both don’t like school.

6: Did talking to girls ever made you nervous?

This question is powerful. The answer to this question is going to tell you a lot more about his past life with girls.

Like, was your boyfriend a ladies’ man? Was he the guy in school who never talked to girls? Was he a shy person or was he outgoing and social with girls?

Ask him this question to find out. Usually, a guy who is comfortable around girls will most probably remain that way. But a guy who is shy and kind of an introvert may have a harder time communicating his feelings to his dream girl or crush. Depending on his answer to this question, also ask him how he decided to ask you out.

7: Were you ever a momma’s boy? 

Most of the time guys don’t like to admit that they are or was a momma’s boy.

It is assumed that guys who are momma’s boy can not take care of a woman or handle a relationship in a manly way.

To get the true answer for this question, make sure to tell him that you don’t really care if he was a momma’s boy and you only care about what he is right now, not what he was.

8: Were you an early or late bloomer? 

Many people are actually affected by this.. Puberty is very unkind to some of us.

For example, If you grew really tall too fast, you felt awkward. And yet, if you were the runt of the group, you had something to prove. Ask your boyfriend this question to find out about him even more. As mentioned earlier, this type of questions are better asked on a face to face conversation rather than texting.

9: Have you ever seen yourself in a relationship with a girl like me?

This is the game changer question, it’s a flirtatious and fun question to ask your boyfriend.

Let him explain how he pictured his dream girl, was she like you?. Let him explain to you how he thinks about being in a relationship with you.

As he answers this question, in a cute way, stare straight in his eyes and listen carefully to what your man is saying.

10: If you were a girl, would you date a guy like yourself?

Find out if he values himself. Love starts from within, if a guy values and loves himself enough, then he will not have a hard time loving someone else. In this case “you”.

By asking him this question, you will be able to tell if he loves himself and if he thinks that, he is worth someone else’s love. Again, in this case ‘yours’.

It’s a wrap! Those are the 10 questions to ask your new boyfriend, that are the most flirtatious, fun and exciting to ask and get answers from your boyfriend.

Questions are important aspects in conversations, especially when you are getting to know someone at a personal level. There you go 10 Flirtatious And Fun Questions To Ask Your New Boyfriend. Have fun!