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20 Revealing Questions to Get to Know Someone Better

Connecting with someone is never easy. But if you want to understand their personality, try these 20 revealing questions to get to know them in no time.

questions to get to know someone

We’ve all been in that situation, where we’re simultaneously obsessed with someone, but also aware at the back of our minds that we really don’t know them at all. That leads to a whole series of questions, such as, “Do we share any interests? Will I actually like them if I get to know them better? Will getting to know them better increase or decrease the chance of the friendship/relationship lasting?”

Although ignorance may be bliss in certain situations, when it comes to getting to spending time with someone and connecting with them on a personal level, you should know what you’re getting into. Revealing questions need to be asked to try and get to know that person better, especially when it comes to dating, and if they don’t meet the criteria, then it’s time to move on to greener pastures.

What’s in a question?

There are different kinds and styles of questions that can be asked to try and work someone out. The first kind of question is that which tries to discern personal tastes and inclinations–to see if there is an ostensible match.

The second kind is the kind that tries to work out if the person asked is aware/bright enough to realize when certain things should or shouldn’t be said; no one wants to be hooked up with a social pariah.

The third kind is that which, although seeming to suggest a particular choice of answers, is actually looking for the way someone handles the question and, therefore, life. It is up to you, the reader, to decide which is which in the following list.

#1 What do you like to drink? From the working class beer, to the red-wine-drinking sophisticate, the champagne hedonist, and the whiskey traditionalist, what someone chooses as their tipple can tell you reams. [Read: What your favorite drink reveals about your character]

#2 Who would you haunt if you were a ghost? Not really an opportunity to actually see who they would haunt, but to gauge their character. Answers can be cutesie, imaginative, or even downright vindictive—draw your own conclusions.

#3 What’s your most embarrassing memory? Again, it’s not the actual answer that is important, but how they approach it. Them saying they don’t have one shows they’re a little too serious. Happily volunteering the information shows they are confident and comfortable with themselves.

#4 What’s the best birthday present you’ve ever gotten? This is a good way of working out if you’re dating a philanthropist or a materialist.

#5 What kind of cuisine do you like? This can tell you so much. Are they sophisticated and erudite *think French or Vietnamese*, sensual and pleasure-loving *Italian or Thai*, or down-to-earth and straightforward *American or German*?

#6 Do you like children? There’s something honest and refreshing about someone who says they love kids, but don’t want any of their own right now. What’s worrisome is the desperation of someone who says they EXIST to have kids, or, at the opposite end of the spectrum, someone who can’t abide the sight of them. Both are big warning signs for someone who is socially maladjusted. [Read: 60 get-to-know-you questions for a new romance]

#7 When was the last time you talked to your parents? If they can’t even manage to make that basic relationship work, then what chance do you have with them? Of course, an answer of “every day for the last twenty years” contains its own relationship pitfalls.

#8 What kind of films do you like? This is definitely a taste question. Do they like the non-cognitive joys of an action movie, a thinker’s thriller, or something that relies upon beautiful photography and direction? The answer to this question is a dead giveaway to the kind of package you’re signing up for.

#9 Who would you get to play you in a movie of your life? This is a great way to separate an egotist from a self-hater, or a comedian from an earnest ponderer. This question can tell you so much, as it essentially reveals someone’s self-perception.

#10 Are you on social media? Not just a “yes or no” question, but an opportunity to discern to what extent. Are they gregarious or aloof? That’s what this question will immediately inform you of. [Read: 16 attention whore signs to watch out for]

#11 What would your friends say about you? Worth asking, just to bear in mind for when you actually meet those friends. You’ll soon get an insight into how delusional they are—or not.

#12 Which three guests would you have dinner with, alive or dead? Whoever the imaginary invitees are will reveal whether the person asked is a listener, a fighter, a hero, or a lover. Of course, there is no right answer; it all depends on what you’re looking for!

#13 What kind of things do you read? The wrong answer is “nothing,” but otherwise, this is a useful question to work out the cultural proclivities of the person asked.

#14 When was the last time you cried? A refusal to admit to crying displays a lack of emotional maturity—NOT a desirable trait.

#15 What has been your greatest success? This question offers another opportunity to identify the rogue materialist, which might be exactly what some people are looking for. [Read: 10 signs the girl you’re talking to is a 24 carat gold digger!]

#16 What’s your favorite sport? If you’re looking for the Sheldon Cooper type, then you would probably hope for a “none” in response. Otherwise, sports can tell you so much about how people-oriented those asked are, or how sociable. There is a big difference, for example, between a long-distance runner and football player.

#17 What three things would you take with you if you were stranded on a desert island? This question can reveal all kinds of weird stuff. Just keep your incredulity to yourself, and your ears well and truly open.

#18 If you could go back in time, when would you travel to? As in the case of number 17, be prepared for some weird-ass answers. [Read: 50 questions to know if someone’s right for you]

#19 What kind of holidays do you like? This is a traditional catch-and-match kind of question. After all, holidays are an important part of a healthy relationship, and you’re going to need to know if those are times that you will be able to spend together in harmony, rather than bitching about where you could have been!

#20 What question do you most want to ask me? What you’re looking for here is that they even have a question in mind. If they don’t, it shows they’re really not that interested, after all.

[Read: 36 random, naughty questions for flirty guys and girls]

Don’t make the mistake of waiting until you’re practically married to get to know someone. Subtly slip these revealing questions into the conversation, and make sure you know exactly whose toothbrush will soon be gracing your bathroom counter!

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David Cullen
David Cullen
David Cullen is frequently described as erudite, insightful and witty – but only by himself and only after several large glasses of Rioja....