25 Personal Questions to Ask a Boy
Whether you are dating or just getting to know each other, these questions will help you know more about your guy and will be fun for him to answer too! These might even be the questions that lead you down the path to a relationship because you are likely to find a few things the two of you have in common.
11 What is your favorite book?
I think everyone has had to read a book at some point in their life. Whether it be an elementary book, a New York Times Bestseller, or a comic book. He has to have one.
22 Where did you grow up?
This is just fun to find out. There are so many places in the world and all of them have their unique characteristics. They may live in a loft in NYC now but may have grown up in a small town in Oregon next to an old lady who had 42 cats. If they reply that they grew up in a big city, ask what part specifically, or if they had any crazy neighbors.
33 What’s your favorite memory with your mom?
This one is a super personal question and is good for you to find out what his relationship with his mom is like. He probably has a super cute story to tell too. This may take him a little while to answer so possibly come back to this one and the next one if he can’t answer immediately.
44 What is your favorite memory with your dad?
And again, you can find out what type of relationship he has with his dad. This is probably something a little more serious like the first time he drove a car or the first time he felt like a man. Dad’s don’t get as sentimental as moms do usually.
55 Top 5 movies? GO!
This has to be answered fast! No hesitation. Talk about the movies he lists and then name your top five. You might be surprised by what type of movies he is into or how many movies are both in your top five.
66 What moment were you most proud of yourself?
This gives him a chance to tell you what kind of a person he is. If he was proud when he finally punched that high school bully, he might be more of a shy person that needs a whole lot of courage, but if it is when he made his first dollar after starting his business, you know he is goal oriented.
77 What is something really stupid you’ve done?
This one is for your enjoyment if he answers with something funny. If he answers a little more seriously keep in mind for the future that he might be sensitive about the subject. It is super hard to talk about things we are embarrassed about sometimes so you might have to tell him your personal answer to this question first.
88 If you could buy any car, what would it be?
Guys just love vehicles and want to talk about cars any chance they get. Keep in mind what his favorite car is, you could get him a little toy model at some point and it would be great! For one showing him you listen and remember, and two because it would be funny to say down the line, “I got you a 1956 Ford Mustang,” then pull a little toy out of your purse.
99 Have you ever lost a friend?
This one is a serious question and be prepared for a serious or angry response or possibly even a distant not really answering the question response.
1010 What is your favorite sports team
If he even watches sports. My boyfriend doesn’t but I know a lot of guys do. You may even have the same favorite football team which would be a score for you in the area of common interests
1111 If you could go on an awesome vacation with one person where would you go and with who?
This will say a lot about who he holds near and dear to his heart. The destination will also tell you a lot about what kind of man he is. If he says Alaska, you know he is an outdoorsy man. If he says Italy, you know he loves food, art, and architecture.
1212 Were you close to your grandparents?
He may not have had grandparents, but if he did this could be a great talking point. Was your grandma nice and bake you cookies or was she the kind that had an evil dog.
1313 What is your favorite TV series on Netflix
This says a lot about a person our age. Do they like comedies, zombies, Netflix originals, sitcoms?! This could go on forever, and if he mentions a show you also watch, another score for you in the things in common interests
1414 Who is your favorite Marvel super hero?
I’m an Thor kind of girl and my boyfriend prefers Iron Man. Which one is actually better than the other is an infinite battle that will never be resolved.
1515 What was your favorite cartoon when you were little?
I had this conversation with my boyfriend a few weeks ago and turned out we loved all of the same cartoons. It was a very pleasant trip down memory lane. Rugrats, Blue’s Clues, Spongebob, Tom and Jerry… you 90’s babies will know what I’m talking about.
1616 What was your first job?
My boyfriend grew up in the country so his was a little funny, a neighbor hired him to move some things. My first job was at an insurance agency during the summer of my junior year of high school. We both had some funny stories to tell.
1717 If you could go back and redo one thing in your life what would it be?
Get ready for a serious answer again or possibly wanting to avoid answering this question. The important thing to remember when asking more serious questions is let them answer whatever they feel comfortable answering. Also, be prepared to answer the question also. If this is a subject you don’t feel comfortable answering yourself, don’t ask him.
1818 What is your favorite thing to do outdoors?
Kayaking, horseback riding, dirt bikes, running, the list could go on forever. But this is yet another chance for the two of you to have something in common. This question will also give you a good idea of what kind of man he is. Hobbies say a lot about a person.
1919 What was your first cell phone?
Silver Motorola Razr and I loved bluetoothing ringtones from my friends… This is just a fun question to ask. Take you back to your jr. high or high school days when emoji’s weren’t born yet and you had to press an actual button three times to text.
2020 What is your favorite kind of dog?
This is just a fun question for us dog lovers. I could personally talk about different kinds of dogs how boys talk about different brands of cars. If you are both dog people, this should be a great conversation.
2121 Netflix and chill or Gym and work out?
Find out what he likes to do on a daily basis, maybe you can be workout buddies or binge watch a season together. If he is a “gym and work out” kind of dude and you are a “netflix and chill” kind of girl, the two of you might not be the best fit.
2222 What is your dream job?
This is a super personal question because it reveals a lot about his character. My boyfriend wants to be a manager at this huge company he works for and I know it will take a long time for him to reach this goal. But it puts into perspective how dedicated he is. What your guy’s goals or dreams are says a lot about who he is.
2323 Dr. Pepper or Coke?
It is a yet another battle that will go unresolved between me and my man. Lucky for me Thor was on the Dr. Pepper cans awhile back, I think that means they are instantly better than Iron Man and Coke.
2424 Do you have any bad habits?
Everyone has bad habits, but what is considered “bad” is different with everyone. Something I consider a bad habit isn’t to my boyfriend so be prepared for something you aren’t expecting. How he answers could be a good indication of how much of a goody-two-shoes or bad boy he is.