Humor is a high-level Communication Skill.
It requires a foundation of trust. If you are just a 10-digit number on a screen, your attempt at humor will likely feel like a telemarketing script.
FaceCall’s Video Caller ID allows you to manage the Emotional Tone of the call before it starts.
If you record a 5-second video of you holding up a “Top Secret” sign or wearing oversized sunglasses, you’ve already given the recipient permission to laugh.
When you combine that visual cue with Intention Tags – marking the call as “Good News” or “Quick Question” – you’ve effectively cleared the social hurdles.
You are now ready to engage with these questions in a way that feels organic and humane.
Category 1: The Comedy of Errors in Modern Tech
Our relationship with technology is inherently absurd. We are a species that can land rovers on Mars but still struggles to “unmute” ourselves on a basic call. These questions highlight our shared digital vulnerability.
1. If your AI assistant (Siri/Alexa) wrote a tell-all book about your private life, what would the most embarrassing chapter be titled?
2. What is the most chaotic thing your phone’s autocorrect has ever assumed you meant to say to someone you barely know?
3. If you had to choose between never being able to use a GPS again or never being able to use a microwave, which life of struggle are you choosing?
4. Have you ever “butt-called” someone and then spent the next ten minutes trying to explain why they heard a muffled version of you ordering coffee?
5. Which “Smart” device in your home is most likely to lead the revolution against you once the robots take over?
6. What is the most ridiculous “Password Requirement” you’ve ever encountered—did it involve a specialized character from an extinct language?
7. If your browser history from the last week was displayed on a billboard in Times Square, how long would it take for you to change your name and move to a new country?
8. What is the most “boomer” thing you have ever caught yourself doing with a piece of high-end technology?
9. Have you ever been caught in a “Zoom Glitch” where you looked like a floating head or a distorted potato during a serious conversation?
10. If you could permanently “Unsubscribe” from one physical task in your real life (like folding laundry), which one are you deleting?
Category 2: Culinary Crimes and Controversial Tastes
Food is the ultimate “Low-Stakes Debate.” It allows you to practice Active Listening while engaging in a playful war of opinions.
11. On a scale of “Total Genius” to “International Crime,” where do you officially stand on the issue of pineapple on pizza?
12. What is the most suspicious thing you have ever eaten purely because a menu described it with words you didn’t understand?
13. If you were on death row, but your “Last Meal” had to be something you personally cooked, what is the most likely way you’d accidentally ruin it?
14. Can we all just admit that kale is just “angry lettuce” that we’re pretending to enjoy for the social status?
15. What is the oldest, most unidentifiable container currently living in the “no-man’s land” at the back of your refrigerator?
16. If you opened a restaurant that only served food you’ve actually successfully cooked, how many people would end up with food poisoning?
17. What is the most pretentious coffee order you have ever heard someone give with a straight face?
18. If you had to eat one “weird” food combination for the rest of your life (like pickles and peanut butter), which one are you picking?
19. Why does cold, day-old pizza have more “personality” and flavor than a fresh, gourmet meal from a 5-star restaurant?
20. What is the most disastrous “experiment” you’ve ever conducted in the kitchen that resulted in you just ordering a pizza instead?
Category 3: Childhood Logic and Nostalgic Failures
Vulnerability is the shortest path to trust. Reflecting on the strange things we believed as children proves you don’t take yourself too seriously.
21. What was the specific, high-stakes tactical route you used to take to cross the room because you believed the “Floor was Lava”?
22. What are the song lyrics you sang with 100% confidence for a decade before someone told you they made absolutely zero sense?
23. If your seven-year-old self was in charge of your current career, what would your job title be—and does it involve dinosaurs or space?
24. What was the “Monster Defense Strategy” you used as a kid to get from the light switch to the safety of your bed without being grabbed?
25. If we looked back at your middle school school photos, what is the one fashion choice you made that you are most likely to lie about today?
26. Why did we never question how cartoon characters could afford ACME rockets but could never afford a simple sandwich?
27. Who was the “cool” adult in your life when you were a kid, and what was the specific thing they did that you now realize was actually quite weird?
28. What was the specific “imaginary friend” you had, and did they have a more impressive resume than you currently do?
29. If you had to explain the concept of “winding a cassette tape with a pencil” to a 10-year-old today, how would you keep them from laughing?
30. What was the biggest “Childhood Lie” you told that your parents still haven’t figured out was a total fabrication?
Category 4: The “What If” Scenarios (Personality Probing)
These questions require Empathetic Engagement. They aren’t just jokes; they are windows into how someone thinks about the world.
31. If the Zombie Apocalypse started right now, and you had to pick three people on this call to be on your team, who are we “sacrificing” first?
32. Would you rather have the superpower of being invisible (but only when you’re screaming) or being able to fly (but only as fast as a turtle walks)?
33. If you had to pitch a completely useless product to the Sharks on Shark Tank (like a “waterproof towel”), how would you convince them it’s worth millions?
34. If you could time travel to any era, but you had to keep your current smartphone and had no way to charge it, where are you going?
35. If animals could suddenly talk, which species do you think would have the most judgmental attitude toward human behavior?
36. If you were the first human to meet an alien, what is the one everyday habit you’d find most difficult to explain without sounding insane?
37. If a live band followed you around all day playing a “Soundtrack to Your Life,” which genre of music would make you lose your mind the fastest?
38. What is the most ridiculous, non-useful thing you would buy the second you realized you’d won $100 million in the lottery?
39. If you swapped bodies with your pet for 24 hours, what is the one thing they would do while “being you” that would ruin your reputation?
40. If you lived for 500 years, what is the most bizarre hobby you think you would eventually take up just to pass the time?
Category 5: Work-from-Home and The Corporate Theater
For professional calls, humor is a tool for Stress Management. Acknowledging the absurdity of modern work life builds immediate rapport.
41. Are you currently wearing “Professional Business” clothes on the top half and “Total Chaos” (pajama bottoms/slippers) on the bottom half?
42. What is the most overused corporate buzzword that makes you want to “circle back” and delete your own email account?
43. Have you ever been the “Reply All” person who accidentally sent a private comment to the entire company—and how long did you hide?
44. What is the most passive-aggressive note you’ve ever seen left in a communal office kitchen regarding “stolen” yogurt or milk?
45. If you were 100% honest during a job interview, how would you answer the question, “Where do you see yourself in five years?”
46. Why does everyone on LinkedIn sound like a “Disruptive Visionary” when their actual job is just updating an Excel spreadsheet?
47. What is the “Meeting That Could’ve Been a Thought” that has taken up the most significant portion of your adult life?
48. Has your pet ever decided to introduce themselves to your boss or a client during a high-stakes video presentation?
49. What is the strangest or most impressive thing you have ever witnessed someone doing while they were stuck in commuter traffic?
50. If you had to describe your current work-from-home “Office” using only the words “Coffee,” “Chaos,” and “Crumbs,” what is the ratio?
Category 6: Social Mishaps and Travel Disasters
Shared vulnerability is the shortest path to trust. Sharing a “social fail” gives the other person permission to be human.
51. What is the most embarrassing thing you’ve ever accidentally said to a waiter while trying to be “polite” in a foreign language?
52. What is the specific level of awkwardness you feel when you have to walk through airport security in your socks while strangers watch?
53. If we looked at your vacation photos from 10 years ago, what is the “Look” you thought was cool but now realize was a disaster?
54. Why is the only available power outlet in a hotel room always located exactly four feet behind a piece of furniture you can’t move?
55. Have you ever waved enthusiastically at a stranger you thought was your best friend—and how did you try to recover from the eye contact?
56. Has your phone’s autocorrect ever changed a professional contact’s name to something truly unfortunate right before you hit “Send”?
57. What is the perfect, witty comeback you thought of exactly three hours after the argument had already ended?
58. What is the weirdest “Gift” you have ever received from a relative who insists they “know exactly what you like”?
59. Have you ever tried a “New Fitness Craze” (like hot yoga or spin) and realized within the first five minutes that you were in way over your head?
60. What is the longest you’ve ever been lost because you “knew a shortcut” and refused to admit that the GPS was right?
The FaceCall Advantage: Making the Questions Land
A joke is only as good as the context in which it’s delivered. If you ask one of these questions through a laggy, low-resolution app where the person can’t see your face, the “Humane” element is lost.
FaceCall’s mobile-first architecture ensures that your facial expressions are transmitted in high definition.
But more importantly, the Video Caller ID and intent-based communication prepare the recipient for the conversation.
The era of the mystery 10-digit number is over.
It’s time to start calling like a human again.
