20 Questions To Ask A Guy

Like that guy? But feel a bit tongue tied when it comes to making conversation? Here are 20 great questions to get the conversation flowing (and to get him laughing, on occasion).

1. What 3 words would you use to describe yourself?

What 3 words

This is fun, and one that can tell you a lot about a person. Of course, you’ll have to be prepared to answer the same in return.

2. What would you do if you inherited a million bucks?

a million bucks

A great question, and one that can give away a lot about a person. Be prepared for the ‘usual’ answers, such as giving money to family and/or charity. But sometimes, just sometimes, the answer might surprise you…

3. What’s your dream job?

dream job

Be prepared to be amazed by the answer. Many of us have dreams that we’ll never fulfill. But hey – dreams are what makes life interesting, don’t you think?

4. What’s your personality – naughty, or nice?

naughty, or nice

And only you can decide which you’d prefer…

5. What’s better? Asking for permission or forgiveness?

permission or forgiveness

Apparently the go-getters in life would say the latter. Of course, it’s a personal preference, and one that you might have strong views on. Either way, it’s a good conversation starter.

6. If you could date a famous celebrity, who would it be?

date a famous celebrity

OK, don’t ask this one if you’re the jealous kind. But hey – we’re only talking hypothetical here. Because J-Lo isn’t really likely to walk into the room…

7. If you had to give me a nickname here and now, what would it be?

give me a nickname

This is a great question if you want to find out what he really thinks about you. If it’s funny or cute, then you’re onto a winner.

8. What are you most afraid of?

most afraid of

Ooooh – this could well be the start of a deep and meaningful conversation. Or not, if he simply says ‘spiders’… But actually, did you know that a fear of spiders is often the sign of a strong leader? Interesting, but apparently accurate. What a person fears the most says a lot about their personality.

9. What is the most useless thing you know how to do?

most useless thing

We’ve all got ‘useless’ talents. But hey, such things are what makes life fun. You’re bound to be surprise by the answer.

10. What would you NOT do for 5 million bucks?

NOT do for 5 million bucks

This is a great one for finding out about his moral leanings. It can lead to an understanding about what they think is important, and what they think is simply unacceptable.

11. Do you know any magic tricks?

magic tricks

This is always a fun question to ask. And it works even better if you actually have a magic trick you can show him in return.

12. Have you got any tattoos?

got any tattoos

If he says yes, then you’re gonna want to see them. Just keep the ones in ‘personal’ places for when you’re not in public…

13. What junk food hits the spot?

junk food

Even if he’s a gym god, everyone has at least one favorite ‘bad’ food that they yearn for on occasion. And hey, don’t judge him if he can’t decide between Burger King or KFC!

14. Beach or mountains?

Beach or mountains

We’ve all got a fav place that we love – or that we’d like to visit. Is it the beach, or perhaps the mountains? Your choice says a lot about your personality.

15. Boxers or briefs?

Boxers or briefs

A fab ice breaker if you’re the ballsy type who’d dare to ask. Only works if you don’t know him very well…

16. Would you rather be rich or famous?

rich or famous

And no, he can’t answer both! This is an either or question.

17. What’s the most embarrassing thing that’s ever happened to you?

most embarrassing thing

You might need to brace yourself for the answer, because if he’s honest, then it’s almost guaranteed to make you cringe. Of course, you’re then going to have to admit yours…

18. If you could read minds, who’s would you want to read?

read minds

Of course, he might simply say ‘yours’ – in which case it shows he’s interested in getting to know you. But whether he says that or not, it could well lead onto a really fascinating conversation.

19. What would you say to The President if you met him?

say to The President

OK, you don’t want to get into a serious political conversation here. But it’s a great question to find out the answer to. And hey – it’s pretty damn topical right now…

20. What do you think are the nicest things people would say about you? And what about the worst things?

nicest things people would say

If you want to discover a little more about how he perceives himself, then listen closely to his answers. This is a good question to ask if you don’t know him that closely, as well as if you do. It’s always fascinating to discover how other people think of themselves.