10 Questions to Ask a Guy (He’ll Love These)

Does it seem like the guy you’re interested in is just avoiding conversation with you? Or maybe he’s doing that weird thing where he’s giving you “rehearsed answers”. Well that’s no fun at all.

Why do guys clam up like that? For some men, conversation just isn’t their strong suit. For other men they may simply not feel comfortable around you yet. In order to help them trust you and confide in you, you have to start with casual conversation.

“But I’ve tried that! And he still seems distant.”

But don’t lose heart…this doesn’t necessarily mean he’s bored or uninterested. It could just be that you haven’t found the right conversation starter to get him going. But that’s the way guys are. Once you find that topic he really enjoys, you can talk for literally hours! Guys love to talk about their favorite subject and “show off” their knowledge.

So if you’re out of ideas on how to get him to open up, remember these ten questions and let’s get a conversation going.

1. “What do you enjoy doing?” or “What do you do for fun?”

Notice this question is far more casual and fun than “What do you do?” which makes it sound more formal and status-related. This gives the guy an opening to brag about his hobbies, his interests, passions and mindless distractions that he enjoys. Chances are, he really would like to talk about this, since so few people actually ask him.

2. “When you were little, what did dream about doing?”

Great way to make him think back and get in touch with his inner child. Men usually do like to share memories of an innocent time, since it’s not too emotional or heavy a conversation. Thinking about it usually gets him all nostalgic and giggly…so don’t be surprised if it’s a long answer.

3. “What song could you listen to over and over again and never get sick of it?”
OR “What movie could you watch over and over again?”

Not only does this get him thinking and chatting about music, but it’s also a good indicator of what kind of man he is, since he personally relates to this song. Sometimes guys reveal a lot about themselves with their favorite choices in songs, lyrics, and musicians.

4. “What’s your all time ‘worst date ever’ story?”

This is a great question because it safely broaches the idea of dating, but with good humor and focusing on what went wrong. His answer not only gets him laughing and talking but also gives you a good idea of what behavior to avoid on your first date!

5. “What’s your favorite kind of pet?” or “What is your spirit animal?”

You can tell a lot about a man by his choice of pet (or spirit animal) and the way he “loves” in a relationship. Dogs have a reputation of being loyal and enthusiastic. Cats are known to be a little moody but affectionate. Some men may even collect birds or fish or even exotic pets. But of course, the reason you ask this question is just to break the ice and get him to reveal a very personal side of himself. Men really do cherish their pets, especially if they’ve had the little fella for many years. Get him to open up about that furry, feathery or scaly friend and watch those dimples form.

6. Where would you like to go for vacation if money and travel wasn’t an issue?
OR “What’s your ideal dream date?”

Ask him to describe the perfect vacation—which also means the perfect date and honeymoon! What sports or games does he like to play? What country does he want to see? What’s his idea of fun? These can all be answered with this simple hypothetical question.

7. If you could invite three people to a dinner party, from any time in history, who would they be?

Get a deep answer with a simple question. Find out who his role models are, who he likes to read about, and whose history he personally relates to. If nothing else, it really gets him to open up about what qualities in a person he finds interesting.

Don’t be alarmed if he says lists someone odd or weird, because after all, it is a weird question. But this is a good question for discovering the way he thinks.

8. “Who was your first crush?”

This is an easy way to bring up the subject of romance and dating without putting heavy pressure on him. Asking him this is a smart idea since it encourages him to be open with his feelings, gives you insight into what kind of man he is, and lets him revisit the distant past with positive associations.

9. “What’s the funniest way you accidentally hurt yourself?”

Almost everyone has a funny story for this one. Plus, it gets him laughing and actually encourages to open up in a non-confrontational way. Since men do enjoy making a woman laugh, this is a great question to draw him out.

10. “What’s your guilty pleasure?” OR “What’s something that you’ve never told anyone before?

This is a much more respectable conversation starter that still feels a bit naughty and exciting. You’re not asking him to shock you, just to be embarrassingly honest and admit something he might not admit to anyone else. You have a little “secret” shared between the both of you and that’s the start of a good friendship.

Remember the point of these questions is not to challenge him but to ease him into a friendly conversation. Don’t ask him anything too deep, but rather just get him used to the joy of talking to you. To sweeten the idea, react positively to his answers with friendly and animated facial expressions. This is just as much about getting him comfortable with your presence as it is your conversation style.

Don’t give up if he seems to be uninterested or distant. In this case, try going back to more simple conversation starters, like the weather or the location where you’re at to see if that makes him more comfortable.

Men do like to talk, sometimes it just takes a little gentle prodding to get them to start speaking their mind!

About The Author

Matthew Coast

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