25 Random Questions To Ask A Guy That Aren’t Super Basic

1. What Is Your Favorite Sports Team?

There is nothing guys like more than sports so he will enjoy you asking him this. Whether it is football, soccer, or baseball he will for sure have a favorite sports team.

2. What Do You Do For Fun In Your Hometown?

Everyone does different things for fun in their hometown (some more fun than others lol). If he lives in a big city he may go to the major bars. If he is from a small country town he may like to go four wheeling. 

If you are both from the same place you may even find your new favorite spot by asking this question!

3. Do You Know What You Want To Major In/ Career?

Although asking about his career path is a little generic it is a great question to ask to get to know what he is passionate about. If you all share the same career path that will for sure give you a lot to talk about.

4. Have You Ever Traveled Out Of The Country?

Traveling out of the country is a big deal and asking this will most likely bring up some really cool stories. You may even find the next place you want to travel by asking this!

5. What Is On Your Bucket List?

Whether it's in your head or written out, most everyone has a bucket list. If you guys share the same one you could plan to check it off together.

6. What Is Your Favorite Concert Or Musical Festival You Have Been To?

One of my favorite things to do is go to concerts and music festivals and I know a lot of guys that do too. This will give you insight into what kind of music he likes and maybe you can go to your next concert together.

7. What Is Your Favorite Show To Binge On Netflix?

Asking someone what show they love to watch on Netflix is a go-to question. There are thousands of shows and movies on Netflix and you are bound to have a show you both like in common!

8. Are You Close With Your Family? How Many Siblings Do You Have?

Family is a huge part of most people's lives so you can learn a lot about someone by learning about their family. It's also a great sign if a guy is close with his family if he is a guy you are looking for something more serious than friendship with.

9. Where Do You Vacation?

Everybody has their go to vacation spot and a lot of times they are really different based on where your'e from. This is a great question to ask a guy to see what your potential next vacation spot is too!

10. What Is Your Drink Of Choice?

If you are at a restaurant or a bar thinking of questions to ask, you probably already got this one answered. But, a lot of people order waters when going out to eat and save their favorite drinks at home. Maybe ya'll can share some killer drink suggestions.

11. Where Is Your Family From?

I always love hearing about where friends families are from because some places are so different! You could even ask where his ancestors are from or what his heritage looks like.

12. What Is Something You Are Good At Not Many People Know About?

This question is a little more personal and will make them think a little! A little humble brag is definitely acceptable here.

13. Do You Have Any Unique Talents?

Everyone has that one talent that not many people know about. This is a great question to ask because it will allow the guy to brag a little. Who knows maybe he is ambidextrous or can sing super well!

14. If You Could Live Anywhere Where Would It Be?

I don't know about you but I am always day dreaming of where I would live if I had no restrictions. Asking a guy where he would want to live can bring up some great travel stories or even give you a look into what he wants in his future.

15. What Is Your Favorite Holiday?

This question is great for two reasons. One, who doesn't love talking about holidays?! They make the year so much more fun. Second, it will bring up family traditions he celebrates and you guys will have fun sharing how each of you celebrate!

16. How Did You Meet Your Best Friend?

Asking about how a guy met his best friend can bring up so many fun childhood stories from the past. Even if they met their best friend later on in life, it's still fun to hear how they met!

17. If You Won The Lottery What Is The First Thing You Would Buy?

I personally love this random question to ask a guy because it lets you day dream for a minute! I could sit for an hour and talk about what I would buy and do if I won the lottery.

18. What Was Your First Job?

I don't know about you but I have some pretty weird and funny stories from my past jobs. This question will for sure bring up some funny stories.

19. Do You Have Any Pets?

Everyone loves to talk about their pets! If they don't have on already you could ask what pet they would want if they got one.

20. What Is Your Favorite Restaurant?

Maybe this question is a little basic but it's still a great question to ask. Now you will know where to go eat next time ya'll hang out!

21. What Is Your Worst Habit?

Whether it;s nail biting, playing too many video games, or skipping school, everyone has a bad habit! Who knows, maybe after you ask this you could help keep him accountable to stop!

22. What Is The First Thing You Would Do If You Were A Girl?

This question is actually so funny and something he has probably thought about before. I know I have thought about what I do would in a day in a guys life!

23. What Is Something You Would Never Do?

You could even spice up this question by asking, "What is something you wouldn't do even for one million dollars?" This really makes the question more interesting.

24. What Is Your Biggest Regret?

Asking a guy his biggest regret can get a little deep but it will for sure bring you both closer! Honestly, he may even say something dumb that you guys will laugh about.

25. What Is Your Most Prominent Childhood Memory?

This question is really fun! Everyone has that one childhood memory they remember for some really odd reason. This can bring up some really fun conversations!

This post was all about random questions to ask a guy.

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