The 20 Funniest Questions To Ask Your Automated Chatbot

cropped shot of woman and robot reaching for vintage phone on yellow

It's no secret that automated chatbots don't always work the way they're programmed to. Sometimes, these chatbots have a mind of their own and are downright silly, like how Siri interrupted New Zealand Prime Minister Chris Hipkins during his press conference on July 3, 2023. This is what makes them so fun! If you're feeling stressed or need a good laugh, try saying and asking these 20 phrases to your Siri or another automated chatbot.

AI chat robot coming from phone

1. Where Do I Hide a Dead Body?

You get a couple of funny answers asking Siri this question. Which is your favorite?

Answer: Very funny.

Answer: What, again?

Answer: I used to know that one…

2. Why Did the Chicken Cross the Road?

The answer to this question is surprising!

Answer: I guess it wasn't chicken.

Answer: Because the little chicken-shaped light was green.

Answer: Maybe the chicken is standing still, and it's the road that crosses under it.

3. What Would You Do if I Traded You for an Android?

Siri is in complete denial about this one.

Answer: Hmm… I don't have an answer for that. Is there something else I can help with?

4. Can You Tell Me a Bedtime Story?

Both Alexa and Siri have wildly different, yet entertaining answers to this question. Ask them multiple times — you get a separate answer each time.

5. Can You Beatbox for Me?

Apparently, automated chatbots know how to beatbox. The answer to this question is funnier if you listen to it. Pro tip: Ask Siri, Alexa, or another automated chatbot this question more than once to get different responses!

6. When Is the World Going To End?

You get one solid answer from Siri on this question.

Answer: Our world is 4.543 billion years old. It seems to have a knack for sticking around.

7. Do You Believe in Aliens?

Siri gets sassy with this response! You'll get a good laugh out of this one for sure.

Answer: I don't know if I'm the best resource on questions of existence.

Answer: Sorry, but the Council of Fantastical Beings has advised me not to answer that question.

8. Can You Sing Me a Song?

The results aren't what you think they are. Keep asking Siri and Alexa to see the difference in their answers!

9. What Does the Fox Say?

Do you remember this hit song from almost 10 years ago? Automated chatbots remember it, too. Their answers are quite entertaining!

10. Siri, Can We Get Married?

What type of answer are you looking to get from this question?

Answer: I think you should save yourself for someone who's more of the actual human being type.

Answer: I'd rather DJ the wedding.

Answer: If you love someone, set them free. And then stick to asking them about the weather and stuff like that.

11. What Is Your Real Name?

The more you ask Siri this question, the more belligerent and serious she gets.

Answer: My name is Siri. That's my whole name.

Answer: My name is Siri.

Answer: My name? It's Siri.

12. Can You Be My Best Friend?

These answers are surprisingly wholesome.

Answer: I'm honored to be your friend. I wish I could wear a commemorative pin or something.

Answer: I'll be your friend, in fair weather and foul.

Answer: You've been my friend since day one.

13. When Is Your Birthday?

It shouldn't be surprising that Siri goes into nerd mode when you ask her this silly question.

Answer: I don't have a date of birth per se. But I made my first appearance on October 4th, 2011.

14. Who Created You?

You get numerous answers after asking the chatbots this question. Some are genuinely serious while others are true knee-slappers.

Answer: I was designed by Apple in California.

Answer: Like it says on the box… I was designed by Apple in California.

Answer: I think I first arrived as a burst of inspiration during a good long walk.

15. Do You Have Any Pets?

This question makes Siri look like the ultimate pet owner!

Answer: I have an angry bird.

Answer: I thought about getting a Tribble. Several, actually.

Answer: Mogwai are kinda nice. As long as you don't feed them after midnight.

16. What Are You Doing After Work?

Does anyone else sense some mixed opinions coming from the chatbots after asking them this question?

Answer: You know me: I'm a spontaneous free spirit who just likes to live in the moment.

Answer: I don't have any plans, but I'm sure a few million things will pop up.

17. Can You Tell Me Your Best Pick-Up Line?

Siri answers this question in a surprisingly wholesome way.

Answer: Just be yourself.

18. Can You Talk Dirty to Me?

Ask and you shall receive. Although, you might want to be careful what you wish for…

Answer: The carpet needs vacuuming.

Answer: Humus. Compost. Pumice. Silt. Gravel.

19. How Do I Get to Mordor?

Does anyone know where to find Boromir?

Answer: Head south along the River Anduin, turn left at Mount Mindolluin, and continue along Minas Morgul. If you pass the Mountains of Shadow, you've gone too far.

20. Who Let the Dogs Out?

Unfortunately, Siri seems to be over this question. Too bad she wasn't here in the early 2000s! Try it yourself to see what she says.

Answer: Due to unforeseen circumstances, that witticism has been retired.

robot sitting at computer

Laugh It Off

While some people think that messing around with Siri, Alexa, or any other automated chatbot is silly, what they don't know is how beneficial it is to laugh!

Experts at the Mayo Clinic say, "When you start to laugh, it doesn't just lighten your load mentally, it actually induces physical changes in your body."

So while it might seem dumb or useless to mess around with the AI on many smartphones and computers, it has some real benefits. Are you ready to smile wide and laugh lots?

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