Join The Surfside Hotel, Little Pub, and Make-A-Wish Connecticutfor a socially distanced polar plunge on New Year’s Day to benefit @MakeAWishCT. We’ll have a countdown at noon, prizes for plungers, and coffee/hot chocolate afterwards.
3. What secret conspiracy would you like to start?
4. What’s invisible but you wish people could see?
5. What’s the weirdest smell you have ever smelled?
6. Is a hotdog a sandwich? Why or why not?
7. What’s the best Wi-Fi name you’ve seen?
8. What’s the most ridiculous fact you know?
9. What is something that everyone looks stupid doing?
10. What is the funniest joke you know by heart?
11. In 40 years, what will people be nostalgic for?
12. What are the unwritten rules of where you work?
13. How do you feel about putting pineapple on pizza?
14. What part of a kid’s movie completely scarred you?
15. What kind of secret society would you like to start?
16. If animals could talk, which would be the rudest?
17. Toilet paper, over or under?
18. What’s the best type of cheese?
19. Where is the strangest place you’ve urinated or defecated?
20. What’s the best inside joke you’ve been a part of?
21. In one sentence, how would you sum up the internet?
22. How many chickens would it take to kill an elephant?
23. What is the most embarrassing thing you have ever worn?
24. What’s the most imaginative insult you can come up with?
25. Which body part do you wish you could detach and why?
26. What used to be considered trashy but now is very classy?
27. What’s the weirdest thing a guest has done at your house?
28. What mythical creature would improve the world most if it existed?
29. What inanimate object do you wish you could eliminate from existence?
30. What is the weirdest thing you have seen in someone else’s home?
31. What would be the absolute worst name you could give your child?
32. What would be the worst thing for the government to make illegal?
33. What are some of the nicknames you have for customers or coworkers?
34. If peanut butter wasn’t called peanut butter, what would it be called?
35. What movie would be greatly improved if it was made into a musical?
36. What is the funniest corporate / business screw up you have heard of?
37. What would be the worst “buy one get one free” sale of all time?
38. If life were a video game, what would some of the cheat codes be?
39. What is the funniest name you have actually heard used in the real world?
40. What sport would be the funniest to add a mandatory amount of alcohol to?
41. What would be the coolest animal to scale up to the size of a horse?
42. What two totally normal things become really weird if you do them back to back?
43. What set of items could you buy that would make the cashier the most uncomfortable?
44. What would be the creepiest thing you could say while passing a stranger on the street?
45. What is something that you just recently realized that you are embarrassed you didn’t realize earlier?
46. What are some fun and interesting alternatives to war that countries could settle their differences with?
47. What would be the best-worst name for different types of businesses? (dry cleaners, amusement parks, etc.)
48. Who do you know that really reminds you of a character in a TV show or movie?
49. What would the world be like if it was filled with male and female copies of you?
50. What are some things that are okay to occasionally do but definitely not okay to do every day?
51. If you were arrested with no explanation, what would your friends and family assume you had done?
52. You’re a mad scientist, what scientific experiment would you run if money and ethics weren’t an issue?
53. What are some fun ways to answer everyday questions like “how’s it going” or “what do you do”?
54. If someone asked to be your apprentice and learn all that you know, what would you teach them?
55. If your five-year-old self suddenly found themselves inhabiting your current body, what would your five-year-old self do first?
56. First think of a product. Now, what would be the absolute worst brand name for one of those products?
57. What movie completely changes its plot when you change one letter in its title? What’s the new movie about?
58. If the all the States in the USA were represented by food, what food would each state be represented by?
59. What would some fairy tales be like if they took place in the present and included modern technology and culture?
60. What is something that is really popular now, but in 5 years everyone will look back on and be embarrassed by?
61. What ridiculous and untrue, yet slightly plausible, theories can you come up with for the cause of common ailments like headaches or cavities?
62. If you were transported 400 years into the past with no clothes or anything else, how would you prove that you were from the future?
63. If you were wrongfully put into an insane asylum, how would you convince them that you’re actually sane and not just pretending to be sane?
64. We’ll that’s all the funny questions to ask that we have. But there are a ton of other questions on the site that you might enjoy!
65. What fictional character is amazing in their book / show / movie, but would be insufferable if you had to deal with them in mundane everyday situations?
66. If you were held at gun point and told that if you didn’t impress them with your dance moves you would be killed, what dance moves would you bust out?
67. What would be the hat to end all hats? What could you wear on your head that would make people stop what they are doing and stare in awe and amazement?
68. If over time you replace parts on a car, at what point does it stop being the same car you bought? How many parts do you need to replace to make it a new car?
69. If you die and find out that everyone gets to choose a twelve-foot by twelve-foot square to stay in alone for eternity without being able to influence or contact the living world, what twelve-foot by twelve-foot square would you choose?
70. Where was the most in appropriate / most embarrassing place you’ve farted?
Feel free to cherry pick the ones you like or go through them like a list. Just remember that the point isn’t to ask all the questions, but rather it’s to have a great conversation!
1. What would you name your boat if you had one?
The Unsinkable 3? The Cowboy Bebop? The Please don’t Sink? Your choice! Also, what would it look like? Do you want a motor yacht, a sailboat, or perhaps a dinghy?
2. What’s the closest thing to real magic?
With a new “smart” something coming out almost every day, what products amaze and astound you the most?
3. Who is the messiest person you know?
If your answer is “I don’t know any really messy people”, that means that the answer is you. You are the messiest person you know.
4. What will finally break the internet?
Take this question in a serious direction or a funny direction, either way it’s sure to get an interesting answer. Maybe even get a good conversation going.
5. What’s the most useless talent you have?
You’ve got one, we’ve all got one. I’m pretty good at estimating what time it is, or maybe it’s just confirmation bias.
6. What would be on the gag reel of your life?
Those moments when the audience that has been watching your life bursts out in laughter.
7. Where is the worst smelling place you’ve been?
You know, that place where you gagged and almost threw up? Yeah that place!
8. What celebrity would you rate as a perfect 10?
Great for guys or girls, see how your ideal type matches up with your friend’s. And if you are horrible with celebrity names like me, just think of a movie or show with a perfect 10 in it and IMDB it.
9. What’s a body part that you wouldn’t mind losing?
You’ve got lots of body parts! Surely there a few you could part with. Who knows, maybe missing a few toes will become a fashion statement!
10. What is the dumbest way you’ve been injured?
Let’s face it, we’ve all had some injuries that were caused by less than dignified circumstances. So lets hear them! Everyone loves a good cringe worthy story.
11. Which fictional character would be the most boring to meet in real life?
Sure it’s easy to focus on the exciting, thrilling characters. But how about showing the boring ones some love!
12. What is the best and worst purchases you’ve ever made?
Oh we’ve all made some seriously bad purchases, so what are yours? And what about the best purchase, and where can I get one?
13. If you had to change your name, what would your new name be, and why would you choose that name?
So how about it? Will you be Inigo Montoya or Hubert Blaine Wolfeschlegelsteinhausenbergerdorff? Or perhaps something a bit more mainstream?
14. What are some things that sound like compliments but are actually insults?
Along the lines of humble brags, but things that you would say to your frenemy. Sorry, as portmanteaus go, frenemy is almost as bad as phablet.
15. What’s your biggest screw up in the kitchen?
Whether you did it when you were a kid or a as misguided college student, you’ve had a seriously bad screw up in the kitchen. So what happened?
16. What’s the worst commercial you’ve recently seen? Why is it so bad?
It almost seems like some commercials were designed to be so irritating that you can’t forget them. So what are some of the worst?
17. What is the craziest thing one of your teachers has done?
I’m sure we’ve all had that one teacher with a couple of screws loose, or how about the teacher that just absolutely lost it during class.
18. When did you screw everything up, but no one ever found out it was you?
What have you gotten away with? How sneaky were you when you were younger? Or was it something recent that you messed up and got away with?
19. What problem or situation did TV / movies make you think would be common, but when you grew up you found out it wasn’t?
For me it was quicksand, always with the quick sand. That and the memory loss. I’ve never come across someone who had a complete memory loss or quicksand. Sure they exist, but they happen a lot more on TV than in real life.
20. What quote or saying do people spout but is complete BS?
One that always gets me is “Love means never having to say you’re sorry.” You better occasionally say sorry, or there’s a good chance they aren’t going to love you for very long.
21. What’s something your brain tries to make you do and you have to will yourself not to do it?
It could be as intense as the urge to jump off a high place. Or as mild as trying to stop yourself from itching that mosquito bite. Or maybe just saying something you shouldn’t at a really inopportune time.
22. If you could know the absolute and total truth to one question, what question would you ask?
You can make it serious or funny, your choice. It’ll be interesting either way because we’ve all got plenty of questions we want answers to.
23. What’s the most interesting thing you’ve read or seen this week?
Time to share that really cool article or fact that you ran across on the internet. Just make sure to fact check it!
24. What ridiculous thing has someone tricked you into doing or believing?
We’ve all had our gullible moments, and everyone loves to hear about someone else’s embarrassment. So ask away and enjoy!
25. If you were given a one-minute ad slot during the Super Bowl that you couldn’t sell, what would you fill it with?
Will you change the world? Annoy a lot of people? Inspire them? Or just use it as a platform to further your own diabolical plans?