60 Questions To Ask To Get To Know Someone

Getting to know someone new can be intimidating. How do you approach them? What do you say to them once you’d actually got them on their own? How much do you actually want to know about them- and how far is taking it too far? With our sixty easy-to-remember questions, you won’t have to worry about being lost for words any more- just try not to blurt them out all at once unless you want some very weird looks indeed…

1. What do you do for a living?
This is an obvious one, but one that has the potential to turn into a really interesting, full-blown conversation. If they hate their job, you’ve got something to complain about, and if they love it you can get some real conversation about why it’s their dream career.

2. How long have you lived here?
This is great if you chatting to new workmates or college companions, as you might be able to find someone who’s lived there a while and knows all the cool hangouts and the places with the cheapest beers- never underestimate.

3. Where did you go to school?
Talking about colleges is seen as the reserve of people who have nothing left to talk about, but sharing college experiences can be interesting- find out whether they loved it, hated it, or any combination of the above. And if they share your alma mater, even better!

4. Where is your favourite place to eat?
As well as scouting out some potentially awesome new eateries, you can find a way to make a friend-date out of this one, as they might have this one dish that they totally have to show you…

5. What’s the most fun you’ve had this week?
Bringing up a recent, fun experience is a great way to bond, and this one we’ll really get them thinking about what made them happy.

6. Who’s your oldest friend?
Everyone has that one friend from childhood who’s just been around since forever. Find out who their’s is, and watch the nostalgia fly.

7. What’s the last movie you went to see?
….and what did they think of it? Gauging someone’s taste in movies can be fun, and a good way to work out if you share interests.

8. What’s your least favourite food?
Everyone has a certain cuisine that just makes their stomach turn, and you’d be surprised at the bizarre answers you’ll get to this seemingly straightforward question.

9. What’s the sweetest present you’ve ever received?
Everyone likes talking about and remembering that one time that their mom, boyfriend, or best friend was so on the ball with their thoughtfulness game- find out what gift really made them feel special.

10. What’s the worst roommate you’ve ever had?
Apart from the lucky few who could always afford their own places, everyone has a roommate-from-hell story- just pray that they aren’t talking about one that they still live with!

11. How would you describe yourself in five words or less?
This one is a real head-scratcher for some people, as we often focus on how other people view us and what they make of us instead of how we feel about ourselves.

12. What’s your worst habit?
This one should provoke a few cringes as everyone tries to pinpoint their most irritating, silly, or plain childish habit-being late all the time, picking at food, making terrible jokes…

13. What’s the worst haircut you’ve ever had?
Again, this is a question meant to make people feel grateful for what they have now. Hair disasters are part of everyone’s life experience, whether it’s hacking off your locks with scissors when you’re ten or going for an ill-advised bob at twenty…

14. What subject would you most like to study?
Most people have a small fascination with at least one academic subject, one that they’ve probably toyed with studying on a deeper level before. What’s theirs?

15. What would be your perfect pet?
And we’re not just talking dogs and cats here- if there’s any animal that they think would be perfect for their lifestyle, they’ve got to spit it out now. An elephant to ride to work? A guard-tiger?

16. What’s your perfect job?
If they haven’t already got it now, find out what exactly would float their boat in the world of work- whether they want to be a candy taster or a brain surgeon, we all have our secret dreams.

17. What TV show character are you most like?
There’s always one show that you watch because you secretly believe that you’re just like one of the starring characters. Are they a Joey from Friends? Or more of a Jessie from Breaking Bad?

18. Where would you love to live?
If you can get your tongue around this one, finding out where they would love to live is often a really interesting question- would they never considering moving out of the city, or are they a bumpkin at heart?

19. What book changed your life?
Even if they’re not really a big reader, everyone can name one book that had a profound effect on the way they live their lives, even if it’s just to avoid hotels called The Overlook.

20. What instrument would you play If you could?
Are they more of a dignified orchestra cellist, or would they be rocking it up on stadium stages with the best of them? An insight into their taste in music is advised.

21. Which three songs would you listen to for the rest of your life, if you had to pick?
You’ll find everyone umming and awing over this one for a while, because choosing that perfect selection is next to impossible.

22. If you could get drinks with anyone, who would it be?
Living or dead, allow them the choice of a lifetime- to hang out with the one person they secretly know they wouldn’t really have a chance to get to know. This can be very revealing- do they want intellectual chat or a good flirt?

23. What’s the most adventurous thing you’ve ever done?
Whether it was something as simple as moving away from home for the first time, to quitting their job to take off around the world, seeing what their most adventurous moment is will tell you a lot about them as people.

24. What’s the sneakiest thing you’ve ever done?
You’ll find a lot to laugh about with this fun question, as they might come up with something embarrassing, funny, or just plain funny that they did in the name of cunning.

25. What one song were you obsessed with as a teenager?
It might be something seriously angsty and moody to reflect their goth stage, or it might be something bubblegum and pop to show off their party-girl/boy style- but their defining teenage song will say a lot about them.

26. What one embarrassing moment would you wipe from history?
Everyone has one moment that they would much prefer to be cleansed from the memories of everyone who witnessed it, even if it was just them-share your cringiest moments and be absolved.

27. What’s your idea of the perfect first date?
Would they rock an adrenalin-junkie sky-diving experience, or are they more fond of a quiet dinner and drinks? And have they had the perfect first date already?

28. What one skill do you wish you could master?
Whether they’d want to pick up something handy, like woodwork or DIY, or learn how to make clothes or play an instrument, this is a good way to suss their priorities.

29. What childhood activity do you wish you could still do now?
Whether it was messing about with the cool games in gym class, or having an afternoon nap and not being frowned upon, what would they bring back in style?

30. What celebrity would you like to be for a day?
Whose life would they take over if they were given the chance? Would they want glamour, glitz, and the red carpet, or would they be more interested in adventure and travelling the world?

31. If you could change one thing from history, what would it be?
It might be that they do something noble and great, or it might be that they would just discourage that awful prom dress they were so deluded about. Who knows?

32. If you were a millionaire for a day, what would you do?
With money being no object, what would they take it upon themselves to do? Would they spend, spend, spend on expensive treats for themselves, or would they do something a little more charitable with their cash?

33. What foreign food are you secretly desperate to try?
It might be that they’ve just not had the money or the chance to come across this amazing-looking foreign food yet, and hey, you might even be able to recommend a place!

34. Which one book do you wish they taught in schools?
Do they think there’s a particular bit of text that would do so much good if kids got to read it too? Or is there just a novel that that they wished they had been introduced to in high school?

35. What’s the name of the movie about your life?
Hell, don’t pretend we all haven’t thought about it at some point- would it be a noble struggle or a screwball comedy?

36. Who would play you in the movie of your life?
Much like the question above, this will tell you a lot about them- do they see themselves as a love goddess or a nerdy wise-cracker?

37. What one fashion trend do you just not understand?
It might be that they just can’t pull it off, or it might be that they’ve never seen anyone look good in it- but everyone has a trend that just baffles them.

38. What one movie would you take a first date to?
It might be a super-romantic drama, or it might be their favourite action movie, but picking the one movie you’d show to potential partners is a tricky one.

39. What’s your favourite photograph of yourself?
Maybe they just look really, really hot, or maybe it’s a memory of a time and a place, but we all have one photo that always makes us smile.

40. What’s your favourite drink?
Are they a red wine and cheese kind of drinker, or do they like to throw back a few beers with the guys? Or maybe they’re teetotal?

41. What TV bar do you wish existed?
Would they prefer to hang around with the cast of Cheers, or are they more into McClarens from How I Met Your Mother? We’ve dreamt of lazing about in that perfect, fake bar.

42. What’s the weirdest talent you have?
Sure, you’ve seen them do that weird thing with their face that you’ve never seen anyone else pull off before, but what do they think is the most unique talent they have?

43. What’s your perfect pastime?
If they had half an hour to spare, what would be there ideal way to fill that time? And how often do they get to do it?

44. When was the last time you gave a high-five?
This is a fun question, one that will let you know what they deem high-five worthy, and one that will hopefully grab you a fun anecdote into the bargain.

45. What’s the coolest story about yourself?
You might be flattering them here, but why not: find out which story secretly makes them feel like the Fonz whenever they tell it.

46. What’s your perfect residence?
Would they like something more stable, like a cool apartment or suburban house, or are they more adventurous, preferring to eke out a living in a caravan?

47. What song sums up your life right now?
What you’re asking, basically, is which song they were looking out of a window and listening to on the bus this morning, thinking “this is totally about me”.

48. What’s your go-to dance move?
Maybe they’re a really good dancer and you’re going to be put to shame, or perhaps they rock seriously old-school, terrible moves that you can get down with.

49. What’s the ultimate ice-cream flavour?
Do they rock it with strawberry and cream, or go old-school with plain chocolate? You’ll be surprised at the strong reactions this garners.

50. What’s the best burger you’ve ever eaten?
You can replace “burger” with any foodstuff, basically, and still take great joy in seeing their eyes glaze over as they recall the finest one they’ve ever had the pleasure of putting in their face. Drool.

51. What junk food couldn’t you live without?
Maybe they’ve got more of a sweet tooth and would go for chocolate over chips; either way, find out what’s top of their shopping list after a hard day at the offce.

52. Are you an early bird or a night owl?
Prepare to be jealous at their ability to party up late, or get to work on time, depending on their answer. Best not to ask a night owl this if it’s before midday.

53. What’s the scariest movie you’ve ever seen?
This one is bound to send some shudders down their spine; what exactly flips their switches and turns them into a quivering wreck of a human being?

54. What’s the funniest movie moment you’ve ever seen?
You’ll be surprised at how obscure these answers can get thanks to those weird range of things that tickle people, as they giggle their way through what particular scenes had them rolling in the aisles.

55. Which planet would you visit?
Not everyone would jump at the chance to go to space, but everyone has dreamt about flitting off to another world, if only for a bit of peace and quiet.

56. Which childhood movie do you still love today?
It could be anything from The Muppets Movie to The Little Mermaid, but we all have a movie that we saw growing that still has the power to enchant us even today.

57. Which song can you never not dance to?
Simple, really: once they name the song, put it on to find out if they’re telling the truth.

58. What’s the coolest item of clothing they own?
Hopefully they’ll be wearing it for easy identification, but if not you can demand the chance to swoon over it some other time.

59. What’s your secret phobia?
Be nice: don’t use this against them at a later date, no matter how tempting it might be to freak them out in a clown costume.

60. Would you ever move back in with your parents?
Would they consider going back to the bosom of their familial home, and what would be the circumstances that drove them there?