Social & Fun
Party games, icebreakers, hypotheticals, and entertaining conversation starters.
Questions to Ask Michelle Obama
Questions for the interview you are unlikely to get and the conversation you can still enjoy imagining: the years before the public ones, what a day inside that life looked like, raising children while the cameras were on, and what she has stopped explaining to people.
20 questions
Funny Questions to Ask Military Personnel
Twenty light questions to ask someone in the military without wandering into anything sensitive: the strangest thing they have eaten in the field, basic training stories, how they explain their job to civilians without jargon, and the habits they cannot switch off at home.
20 questions
Minecraft Questions to Ask Your Friends
Questions to ask your friends about Minecraft, for a voice chat while you mine, a long car ride, or the pause before someone starts a new world together: how they play, what they have built, what they refuse to do, and the arguments worth having.
20 questions
Funny Questions to Ask Mom
Twenty questions that ask your mom to own up to the parts of raising you she has never volunteered: the cover stories she wrote for you, the house rules she invented on the spot, the things she quietly threw away, and the enthusiasm she faked for a solid year. The person being teased here is mostly the parent she was at thirty, which is what keeps it comfortable. If you would rather she did the teasing, the set on what she really thought of you growing up points the other way.
20 questions
Questions to Ask Monkey Paw Phasmophobia
Questions to put to a more experienced Phasmophobia player about the Monkey Paw: how a wish is actually made, what each one costs, when in a run it is worth using, and how to coordinate with a team before anyone says a wish out loud.
20 questions
Good Music Questions to Ask
Questions about someone's music: the song that reliably fixes a bad mood, their first concert and first album, the record they play end to end, the genre they hide, and the track they always skip.
20 questions
Funny Questions to Ask Musicians
Twenty light questions to ask a musician backstage, on a podcast or over drinks: what their instrument would complain about, the song they never want to be asked for again, the worst venue they have played, and the gear purchase they still regret.
20 questions
Good Questions to Ask Musicians
Questions for interviewing a musician or just talking with one: where songs start, what they do when nothing comes, the shows they still think about, which criticism turned out to be right, and how the money works.
20 questions
Questions to Ask Musicians
Light questions for hanging out with musicians after a gig or in the van, about strange venues, gear they would run back for, requests they refuse, and everything the audience never notices.
20 questions
Naruto Questions to Ask Your Friends
Naruto questions for a group chat, a rewatch night or a long car ride, moving from easy favourites into the arguments the fandom never settles: Itachi, Sakura, filler, talk no jutsu, and whether Naruto earns the hat.
20 questions
Questions to Ask on a Car Ride
Questions built for the car, where you are side by side instead of face to face and nobody can leave. Starts with easy road and driving talk, then moves into the longer, more reflective questions that suit the middle of a drive.
20 questions
Questions to Ask on a Coffee Chat
Questions for a short informal chat with someone whose work or career you want to understand, whether you asked for the time or they offered it. Covers how they got there, what the job is actually like, what they would do differently, and how to leave with a next step.
20 questions
Questions to Ask on a Live Stream
Questions for a live stream, whether you are typing in chat or hosting and need something to fill a quiet stretch. Each one is short enough to read aloud and open enough to answer while doing something else on screen.
20 questions
Questions to Ask on a Long Car Ride
Questions for a drive that lasts hours: what to settle in the first stretch, what works when the road turns dull, and the slower questions that are easier to answer when nobody has to make eye contact.
20 questions
Fun Questions to Ask on a Road Trip
Twenty questions for the hours between stops, ordered from easy to answer at the start of a drive to worth answering somewhere after dark. Written for a car of adults or a mixed group of friends and family.
20 questions
Questions to Ask on a Road Trip
Questions for a trip of several days on the road: what each person wants out of it, how you both travel when plans slip, and the stories that come out somewhere around day two.
20 questions
Questions to Ask on a Roadtrip
Lighter questions for a car full of people: snacks, music rules, roadside oddities, and arguments worth having at seventy miles an hour. Built for groups and friends rather than for quiet reflection.
20 questions
Questions to Ask on a Speed Date
Twenty questions for the few minutes you get with one person at a speed dating event. They are ordered for a short round: an easy opener, several that get past job titles quickly, and a close that leaves you something to decide on when the bell goes.
20 questions
Fun Questions to Ask on Bumble
Twenty playful openers for a Bumble match who has said hi and not much else. Each one is easy to answer, hard to answer in a single word, and leaves you something obvious to reply to.
20 questions
Questions to Ask on Facebook for Engagement
Twenty question prompts for a Facebook page or group post, ordered from quick ones anyone can answer to slower ones worth saving for an audience that already comments. Each one notes what the replies usually look like.
20 questions
Questions to Ask on Instagram
Twenty prompts for an Instagram Story question sticker or a Q and A box, with notes on which ones fill up with replies, which ones sit empty, and how to reshare answers without losing the people who sent them.
20 questions
Questions to Ask on Instagram
Questions for a direct message conversation on Instagram with someone you have only just started talking to, ordered from easy replies to ones that take more thought, with notes on what the answers tend to show.
20 questions
Questions to Ask on Kahoot
Twenty question ideas to put in a Kahoot for a class, a team meeting, or a party, with notes on how each one plays in the room, how to write the wrong answers, and where the timer needs adjusting.
20 questions
Questions to Ask on Live Stream
Prompts a streamer can put to chat, starting with openers that even lurkers will answer and ending with ones that only work once a stream has warmed up, with notes on how each lands in a fast chat and a quiet one.
20 questions
Questions to Ask on Road Trip
Questions for a long drive, arranged so the easy ones come first and the searching ones arrive later, once nobody has to make eye contact. Written for friends, couples, family or colleagues sharing several hours in a car.
20 questions
Questions to Ask on Road Trips
Questions for a long drive with one or two other people, arranged roughly by how far into the trip they start working, with notes on which ones to keep away from whoever is driving.
20 questions
Questions to Ask on Sendit
Prompts to post on Sendit and other anonymous question apps, short enough to answer in one line and light enough to stay fun, with notes on which ones invite unkind replies.
20 questions
Questions to Ask on Snap
Prompts to send a friend on Snapchat, most of them answerable with one photo, ordered from things anyone will send back to ones that only work with someone you already trust.
20 questions
Funny Questions to Ask on Snapchat
Twenty short questions to send as a snap or add to your story, each answerable with one photo or a few words: which emoji they would be, the last random thing they searched, the food they would rename themselves after, and the strangest thing within arm's reach.
20 questions
Questions to Ask on Social Media
Questions to put to the people who already follow you, whether you run a small business, a newsletter, or a community account, with notes on what the replies tell you and which ones invite trouble in public.
20 questions
Questions to Ask on Speed Dating
Speed dating gives you roughly four minutes per person. These twenty questions are short enough to ask and answer in that time, and pointed enough to tell you whether you want a longer conversation later.
20 questions
Questions to Ask on Thanksgiving
Thanksgiving puts three or four generations around one table for several hours. These twenty questions move from the food to the year behind everyone to family history, so there is somewhere for the conversation to go once the plates are full.
20 questions
Questions to Ask on TikTok
A comment section answers a specific question far more readily than it answers a call to action. These twenty prompts are written to be answerable in one line by someone who has never seen your account before, with notes on where each one tends to land and where it falls flat.
20 questions
Fun Questions to Ask on Wedding RSVP
Twenty questions to print on your RSVP cards, ordered from quick tick boxes to the sentimental ones. Written for couples building a playlist, stocking a bar, working out seating, or collecting something to read aloud at the reception.
20 questions
Questions to Ask on Wedding RSVP
Twenty questions to put to guests across the RSVP window: chasing the people who have not replied, confirming numbers and dietary needs, sorting travel and rooms, and the quiet questions that make a table plan work.
20 questions
Questions to Ask Oprah Winfrey
Questions for the interview you will probably never get: how a conversation gets steered, when to stay silent, what gets cut, what she has stopped saying yes to, and what it is like to be read by someone who reads people for a living.
20 questions
