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June 20, 2020

Top 25 Questions to Ask a Guy on a First Date

That first date can be one of the most tricky experiences ever. You will be alone with someone you really do not know. There could be instances of awkward silence where you want to say something but you are not sure what in the world you should say. Here are some of the most important […]

That first date can be one of the most tricky experiences ever. You will be alone with someone you really do not know. There could be instances of awkward silence where you want to say something but you are not sure what in the world you should say. Here are some of the most important and best questions to ask a guy when you are going out on your first date. When it matters to you that this date goes well, it helps to do a bit of planning before you actually walk out the door for that date. It’s the perfect way to learn as much as you can about someone new so you can better determine if this person should be in your life.

1. What do you do in your free time?

This is an important question. Although many guys are happy to talk about work or school, you’ll really get to know them by better understanding what they do during their free time instead. Do they enjoy sports, politics, religion or just hanging out?

2. What’s your favorite food?

It’s a fun question, but it can be the perfect way to break the ice and open up a stalled dinner date conversation. Make sure it’s lighthearted and be willing to share, too!

3. Where did you go to school?

When it comes to top random questions to ask a guy on a date, you’ll want to make sure you get a bit of background. Learn about where he went to school, what he studied, and why. This can provide a fantastic “look” into who he is and what’s really important to him.

4. Do you like to travel?

This is an especially important question in situations where you know the guy does. Talk about the travel experiences you have had, too. You can also choose questions like this that you already know you have a connection with him through to keep the conversation active.

5. Do you like to go to the movies or stay home and watch TV?

This is sure to give you some insight into who he is and what motivates him. It’s also good to know how into culture he is and how well that fits with the lifestyle you enjoy living.

6. What’s on your bucket list?

Again, be willing to share your own. He could answer this question in many, many ways. The key here is to keep talking about hopes and dreams…opportunities and ideas. This is a fun, lighthearted way to learn more about his future plans.

7. What’s your social like life?

You can follow that up directly with, “Do you have a lot of friends around here..” The goal is to get an idea of who he is friends with, how valuable his friendships are, and how much of a role these friendships are likely to spend on your next day out!

8. What did you do today?

It seems like a strange question, but it is the perfect way to offer a bit of interest in his life. Just like you, he wants to know that you are the type of person he can reach out to and care about as well as interact with even on boring topics.

9. What’s your biggest pet peeve?

Of course, you’ll want to make sure you don’t do these things if you want this guy to hang around after this date!

10. Where did you grow up?

If you don’t know this, you can often get many guys talking about their childhood this way. You can then follow it up with the types of things he did as a child to have fun or where his favorite stomping ground is. Chances are good he’ll have fond memories to share with you.

11. What’s your favorite sport and sports team?

Be careful, for some men, this is a loaded question. For others, it is one that will bother them if they don’t like sports. And, be sure that when you ask these questions to ask a man on a first date, that you are giving him plenty of time to answer!

12. Do your parents still live in the home you grew up in? What’s it like?

Again, this is a great way for you to learn about his family and his past. It’s also a fun way to talk about your history and what makes your background interesting.

13. When’s your birthday?

Of course, if things go well you will need to know this information. In all other cases, you’ll want to be sure that you follow this question up with another one so that the conversation isn’t just a few words. For example, after he answers, you can say, “What do you like to do on your birthday?”

14. What are you doing this week?

Be careful with this question. You don’t want to leave him thinking that you are going to invade his every waking moment. Rather, you want to use this as an opportunity to talk about what’s on your schedule and to get to know he typically does.

15. Do you like this place?

If things get quiet, ask a question like this. You can often let a bad experience at a bar or restaurant lead you to a different location if the first place isn’t working. You can also follow it up with, “what are you doing after this” and see what he says.

16. What’s your perfect day like?

When asking a question like this, you can really learn what his true colors are. Look for a guy that’s willing to share what he does not just what he hopes to do. It’s also great information you can use later if you end up planning the next date.

17. When was the last time you went on a vacation?

No, you are not trying to gather information here so you can become a gold digger! But, you will gain some fantastic information about what he enjoys doing, what his experiences are, and what he hopes to do in the future (make sure you ask about that, too!)

18. What are your friends like?

There’s no time to judge here. Get to know him through the types of friends he keeps and find out what everyone tends to do on a regular basis. Give him a chance to talk about something that isn’t directly related to him. That’s important especially if you are asking a lot of questions!

19. What’s something you are really passionate about?

You also want to know why.

20. Do you enjoy your job (or what you are going to school for)?

And, of course, ask him why. It’s a good idea for you to let him talk about his work especially if it is something he’s worked hard to build up or something that seems to be very important to him.

21. What do you want me to know about you?

Sometimes, a guy needs a bit of prompting when he wants to talk about himself. With the help of a question like this, you can let him talk about anything at all. After all, you are both there because you want to share an experience and, in most cases, you want that experience to move on. Find out what he really wants you to know about him.

22. What do you really want to know about me?

Yes, just like the previous question, this is a pretty open one and that’s the point. You want to give him the chance to really ask anything that he may be thinking but may not really want to say. Of course, you still have to do your best to answer this question!

23. Who are you close to?

It’s likely that this may be a friend or a family member. It can give you an idea of what really matters to him.

24. Did you have a good time today?

There’s no reason not to ask this question! If you want there to be another night, ask it!

25. Will I get to talk to you again? (One of the funny questions to ask a guy)

Don’t be pushy with timeframes or even scheduling another opportunity. Instead, keep things open and leave this question open for him to answer, or not.

These are some of the best questions to ask a guy you like when you really want him to get to know you and for you to get to know him beyond what he looks like. It’s also a fun way to start any conversation!

Article written by chopxtix

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