31 Funny Ways To Start A Text Conversation And Get Responses!

Online Dating | | , Content Writer
Updated On: May 6, 2024
Funny Ways To Start A Text Conversation

Whether you’ve known them your entire life or you’ve just met them, texting each other is something that you’re definitely doing. The difficult part is having to start the conversation over text. Everyone’s always asking questions like “What is a good way to start a text conversation?”, or “How to start a conversation in a way that isn’t creepy?” Well, the answer is, Humor. Leading with something funny is the perfect way to start the conversation. It is neither creepy nor boring. 

Knowing funny ways to start a text conversation is a necessary skill these days. You want to make sure that the text is funny, but also relatable. So, the best thing to do is to stick to universally funny things. You’ll want to avoid sarcasm and dark humor until they get to know you better.

How Do You Start Texting Someone First?

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Conversations are difficult. Talking to friends and family is normal, but trying to talk to new people is tough. The biggest problem is having to wait for them to text you. It can be torturous and can seriously test your patience. One thing that you can do is initiate the conversation by sending the first text. This will help you feel a little better, at least now the ball is in their court. 

When initiating the conversation, there are a few things that you should keep in mind. Think of these guidelines as responses to your query, what is a good way to start a text conversation? Here goes:

1. Light-hearted

The initial conversations need to be light-hearted. You want them to continue to talk to you and the best way to get them hooked is by talking about something fun. You can talk about movies, school, college, work, sports, anime… the list goes on. The point is to get comfortable with each other before getting radical or philosophical.

2. Questions

The point is to figure out what kind of a person is at the other end of your text, right? So, what better way to do that than asking them questions? Your questions need to be interesting, things that trigger their curiosity. You can ask about favorite movies, food, actor, song, etc. But don’t get PERSONAL. If you ask questions that pry into their personal life, it might scare them away. Avoid things like:

  • Where they live
  • Their family
  • Sexual history/choices
  • Their job
  • Political opinions
  • Religious faith

Pro-tip, avoid questions with a yes-or-no answer. Ask open-ended questions that will get them talking about themselves.

Related Reading: 8 Rules Of Texting While Dating

3. Compliments

This is the safest way to start a conversation. Whether it’s your first conversation or just a new conversation, starting with a compliment never fails. Choose something specific that you can praise or admire. If you’ve followed them on Instagram, you can complement their post. If you’ve just met on Tinder, you can choose something from their bio. For example, if you’re looking for funny ways to start a text conversation with a guy who says he likes photography you can compliment his talent, but negging is a serious no-no.

Choose things that matter to them for compliments. And steer away from body-specific comments (unless they work out and take pride in their physique). Always keep things classy.

what is a good way to start a text conversation
The key to a good conversation starter is humor along with creativity.

31 Funny Ways To Start A Text Conversation And Get Responses!

Now that you know the basics you should be able to start a conversation with confidence. If you’re still nervous or confused, then chill. We’re here to help you out. Keeping in mind these basics, here are a few, “What to say to start a conversation over text” examples:

1. What is your idea of a perfect date?

If you’re looking for flirty conversation starters this one tops the list. Not to mention it will give you the perfect idea for your first date together. 

2. What qualities matter to you the most?

The answer to this will tell you exactly what they’re looking for. You could be EXACTLY their type!

3. Do you watch comedy movies after watching a horror one at night?

Let’s keep it real. We all do this. 

4. Do you believe in love at first sight?

This is a bit common, but it works every time. (Especially with girls, just saying)

5. What is the worst, first date you have ever been on?

If you’re looking for funny ways to start a text conversation with a girl, this could seriously work. Exchanging ‘crappy date’ stories is the perfect bonding topic.

6. If you could date anyone in the world, who would it be?

Here’s a fun question. Everything is on the table. Actor, athlete, a fictional character. The answer can be anything.  

7. What’s the cheesiest pick-up line you’ve ever heard?

You’ve got to admit this is one of those flirty but funny ways to start a text conversation. Admit it, if you got hit with this question, you’d have fun answering it.

Related Reading: 12 Creative And Impressive Ways To Tell Your Crush You Like Him Over Text

8. What’s the best Wi-fi name you’ve ever seen?

Now here’s a question you don’t hear every day about. Creative and funny, a perfect conversation starter. 

9. If you were a candy bar, which candy bar would you be?

Awww, this is a sweet question. Bet they’ll have to think about it.

10. What emoji sums you up the best?  

We all have an emoji that we relate to. The answer to this will tell you a lot about them.

11. What fictional place would you most like to visit?

Hogwarts or Narnia? What’s your escape from reality?

Related Reading: 30 Texting Games To Play – Game Mode On

12. What’s your go-to comfort food?

If you’re looking for funny ways to start a text conversation with a girl but you also want to create a good impression on her, this is the perfect question. It’s personal and yet pretty nonchalant. 

13. Tell me the stupidest joke you’ve ever heard.

Most people go with funny jokes to start a conversation, but you can always ask them this question and flip the tables. Just be ready with your own stupid joke, it will eventually be your turn.

14. What’s your zodiac sign?

If you’re into astrology, this is the perfect question to ask them. It may not be funny, but it’s a pretty good way to get to know them without being intrusive. 

15. What’s your biggest pet peeve? And why?

Stories about online dating

Everyone has one and they always have the funniest reasons behind them. 

16. Dares

Always fun and they can easily turn into one of those cute but flirty conversation starters. All you have to do is give them a dare like one of these:

  • Dare you to send me your favorite romantic song
  • Dare you to tell me a couple moment on your bucket-list
  • Dare you to meet me for coffee
  • Dare you to tell me how you feel about me

17. Would you rather?

Wondering what to say to start a conversation over text? Just play this game! Here are a few examples to start you off:

  • Would you rather have a horse’s tail or a Unicorn’s horn?
  • Would you rather wear a bathing suit or wear formal attire everywhere you go for the next two weeks?
  • Would you rather live forever or die young?

18. What would you choose as your weapon of choice?

This one is for all you fantasy fans. You guys have all thought about the answer to this, so why not get to know their choice? Their choice will speak volumes about their personality. 

19. What would your dream house be like?

This is the perfect question to ask someone if you want to know more about them. Their choices will tell you a lot about their personality. For all you know you might even get to make their dream a reality someday so this info can’t really hurt.

20. If reincarnation exists, what would you like to come back as?

Well, if you haven’t thought about it till now, here’s your chance to come up with an answer. It’s a pretty funny way to start a text conversation, don’t you think?

21. If you had to choose one superpower, what would it be?

Don’t lie, we all know you’ve thought about it. The fun part about this question is the answer to the “why they want that superpower” part so don’t forget to ask.

Related Reading: The Ultimate Funny Online Dating Questions

22. Do you think Jack could have also fit on the headboard at the end of the movie, Titanic?

I say he could have defiantly fit in it, but it’s a never-ending debate. You might want to ask them what they think. This could be a pretty fun conversation if you guys disagree. A debate can spice things up you know.

23. What’s the weirdest trend you’ve followed?

Embarrassment is a universal feeling, so go on and bond over it. Keep your confession ready too.

24. If you could outsource one thing about your life, what would it be?

Another idea right out of the “funny ways to start a text conversation” book. It’s an intellectually stimulating question too and we bet the answer will very amusing.

25. If you were given 1000 acres of land, what would you do with it?

If you’re thinking about funny ways to start a text conversation with a guy, then this one will definitely work. The guys I know have given me some pretty crazy answers to this question. You should try it out, it will be fun I guarantee it.

26. Captain America or Iron Man?

No one who is a Marvel fan can resist this question. The world is literally divided in two because of this. This is especially true for guys. So, if you don’t mind a nice debate then this is a pretty funny way to start a text conversation with a guy.

funny ways to start a text conversation with a guy
Keep things light-hearted and fun.

27. Is a hot dog a sandwich?

Forget about funny jokes to start a conversation, this is the way to go! I mean come on, does anyone in the world really have an answer to this question? 

28. Which sport would be funniest if the athletes had to be drunk while playing?

Now, this is super fun to imagine. Honestly, the answer doesn’t even matter just thinking about it makes you fall off the couch!

29. If you came with a warning sign, what would it be?

Look out for this answer. It may be a funny way to start a text conversation but the reply will be pretty real. And dare we say, insightful too?

30. What makes you nervous?

Instead of using funny jokes to start a conversation, asking an interesting question like this can often be a lot more fun. Just remember, if they tell you theirs, you gotta tell them yours.

Related Reading: Dating As An Introvert – 9 Tips To Make The Most Of It

31. If you had a credit card with no limit for a day, what would you do with it?

If you are still worried about, “What is a good way to start a text conversation?”, you can just go back to classic questions like this one. It may be old, but it’s still fun to think about.

So, there you have it – 31 funny ways to start a text conversation. Just a few warnings, if you’re asking any of the questions that have been mentioned, then you’d better have your answers ready – the question will definitely come back to you. Honestly, starting a conversation is very simple, the only reason it seems like a big deal is because you’re facing texting anxiety. Don’t overthink things, this is simply the beginning. Even if you don’t start the conversation perfectly, as long as you start talking…that’s what matters. Remember all’s well, that ends well. All the best!

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