Getting to know someone can be easy at first. But what happens when you get past all the obvious, generic questions like, “What’s your favorite movie?” or “How many siblings do you have?” Getting to really know someone takes a bit more cunning and knowledge of how to see through the smoke screen he puts up. There are good questions to ask a guy to really loosen him up and get him out of autopilot answers.
Maybe you’re on a date and the conversation stalls a bit, or maybe you’ve been seeing each other for a while but you’ve started running out of things to talk about. You may just want to shake him up and keep him from feeling nervous around you. Some people are a bit too shy to open up straight away. But when asked the right way, there are some questions that’ll intrigue him and have him telling you more.
# What’s your ex like?
Most guys who tell you their ex is crazy or a bitch, are the ones to be cautious of. Generally, if he has nothing but bad things to say about her, it’s because he’s either not over her, or he’s the one that turned her crazy. [Read: 16 types of guys to avoid like the plague]
# What’s your relationship like with your family? The way a guy relates to his parents is a good indication of what kind of a person he is. They’re the ones who taught him his first impressions of what relationships were all about. In most cases, they taught him how to treat women. If they’re good people, chances are he’ll be a great person too.
# What’s your political stance? Politics either bring about a fruitful, interesting discussion, or spiral into a long-winded rant. Depending on how compatible you are politics-wise, you’ll get one or the other. If he ends up ranting, then he’s probably not right for you.
# Do you believe in monogamy?
This is a tricky one. Depending on what you’re after, you either get the perfect response or hear something you wish you hadn’t. In most cases, if you’re looking for a relationship, hearing that the dude’s just not down with monogamy can be an instant spark killer.
# What’s your biggest accomplishment? Hearing someone’s biggest accomplishment puts into perspective what their priorities actually are. Some guys boast about how much money they make, their year long stint working in an orphanage, or the best frappuccino they ever had. It’s up to you to determine what is and isn’t shallow.
# How would you describe yourself in one word?
This is one of those perfectly good questions to ask a guy because it reveals so much about him, and it’s coming from his own mouth. When women describe themselves, their habit is to be self-deprecating. When men describe themselves, they tell you EXACTLY who they are. If a man tells you he’s lazy, generous, stingy, selfish, or talented, believe him.
# What job would you have if money was not an issue?
A lot of people put their passion to the side in order to get a “normal” job, so seeing where his passion lies when money has no bearing on his life gives you an interesting insight to him.
# What’s the dumbest thing you’ve ever done? Most people can be reckless at times, but there’s a difference between messing up at an important meeting and sleeping with your best friend’s wife. Or accidentally burning down your house. Or wrecking your car while drunk. Be careful what he justifies by saying it was ‘just a dumb decision.’
# How many hearts have you broken? Every man breaks at least one heart. So, if he says none then he’s either lying because the number is much higher than he wants you to know, or he’s incredibly naive. Or emotionally disconnected. Or both.
# If you could master any craft or subject what would it be? This question brings out a side of him that indicates any hidden talents he has. It also shows you his deeper interests and what kind of ambitions he has. A man who doesn’t want to get better at any subject or craft is a man with no passion in life.