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35 Best Text Conversation Starters For The Shy & Socially Awkward

When you’re faced with a flashing cursor, it’s hard to know what to say. Learn some conversation starters for texting and never be stumped again!

best text conversation starters

Starting a conversation can be really difficult. It’s even harder if you don’t really know the person all that well. What do you talk about? How do you actually continue the conversation? You can’t just start with a “hey” if you want it to go anywhere. The answer? Having a good list of text conversation starters ready to go!

If you’re a little shy or socially awkward, you’ll benefit from having something ready to go because it takes off the pressure.

You can avoid sitting there, thinking and taking forever to come up with something. Then, when they reply, you’ll be much calmer as a result.

[Read: Texting your crush: A step-by-step guide to doing it right]

Aside from having conversation starters for texting in your mind, why is texting hard for some people?

Some people can talk in person without any issues, but when it comes to texting, they have difficulties. You’d think they could just transfer their talkative persona to their phone but for them, much of their ability to talk to someone easily comes from the energy and attitude of the other person.

With a text, you’re going in blind. You don’t have body language to read, or a facial expression to work with. There is also a high possibility of misunderstanding one another over text. That’s why some people find it hard to text.

On the other hand, someone who is shy might not know what to talk about, and end up completely stressing themselves out.

In the end, they might not send the text at all. When you have a few text conversation starters in your mind already, all of this is made ten times easier. [Read: The 20 biggest unwritten rules of texting etiquette you should always remember]

30 conversations starters for texting to banish the awkwardness from any conversation

Thankfully, there are plenty of text conversation starters you can choose from. Some of these are actual sentences you can copy word-for-word while others are simply guidelines you can use to get creative on your own.

The bottom line: these will help you get that conversation rolling and take the pressure when the cursor is blinking and your mind is blank!

Let’s start with a few ideas, and work ourselves down to a list of examples you can use as a conversation starter while texting anyone you like.

1. Send a meme you think they’d find funny

Memes are by far the best thing for getting a conversation started. It really only takes sending a single image to start talking. You can even send them memes that remind you of them. The point is to start the conversation without even actually saying anything. Let them reply and go from there. [Read: How to be funny and make people love your company]

2. Ask a question about their hobbies

People love talking about stuff they enjoy. And if you know their hobbies, then you know what they enjoy. It doesn’t take much to get someone chatting about the stuff they do in their free time. Ask them questions about it and what they like most. They’ll probably carry the conversation from there. [Read: 25 very cute ways to say Hi in a text message and start texting]

3. Discuss something major going on around you

This can be anything from big world news to something more specific to where you live. If you find common ground, you’ll be able to get the conversation going easily.

Everyone has an opinion about what’s going on. Get them talking about theirs. [Read: Texting anxiety: How to send & receive texts without freaking out]

4. Follow up with something they told you about

If they told you they’d be going to a concert Saturday, text them on Sunday asking about it. Not only does this show you’ve been paying attention, but it’s one of the text conversation starters that allows them to really do the bulk of the work.

5. Tell a joke

Everybody loves jokes. You can even tell cheesy ones if you want. It doesn’t have to be anything major. Just look up some funny jokes online and send one their way.

You’ll be able to laugh about how horrible it is and the conversation will carry from there. [Read: 70 hilarious and cheesy pickup lines to get anyone laughing over text]

6. “I just saw the funniest video I think you’d love”

This is great if you’ve been watching some YouTube videos or Instagram reels and want to share something with them. It starts a conversation and also gives you something very specific to talk about.

7. “Hey! What’s the name of that band you were talking about last week?”

Opening with this is a perfect way to start a conversation because there are so many places to go from there. You can also alter this to better fit with something you know they were talking about. Clearly, not everyone will have told you about a band last week. [Read: 30 flirty conversation starters examples you can use if you want to flirt with someone]

8. “Have you ever been skydiving?”

This might seem like an out of the blue question, but it’s great because they don’t know the context of it. Maybe you’re thinking about doing it. Maybe you just saw someone else do it. You can talk about how it went if they did and if they want to if they haven’t ever been.

9. “I can’t believe what’s going on right now”

This can be in relation to world news or an event what’s happening where you live. It’s a pretty simple statement but it opens the door to a longer, deeper discussion.

10. “Lol! This is totally something I can see you doing”

Send this text along with a meme or video of someone doing something funny. Just make sure that it’s something that the other person would actually do. Otherwise, it’s kind of pointless.

Making them laugh and relating something to them will definitely get a reply and start a fun conversation. [Read: How to start talking over text – 15 ideas to start flirty banter]

11. “I don’t know what to have for dinner, any suggestions?”

This is a genius idea when it comes to text conversation starters because not only does it come out of the blue, but it might also lead to you asking them to join you for dinner, either at home or in a restaurant. You never know, it might be the start of something beautiful!

12. “Any Netflix suggestions?”

It’s casual, it’s fun, it’s nothing too suggestive, but it could lead to a long conversation about new suggestions and favorite shows. Of course, if this is someone you’re kind of seeing or crushing on, it could also lead to Netflix & chill!

13. “What are your plans for the weekend?”

It’s innocent enough but the fact you’re asking shows that you’re not only interested but possibly going to suggest something you could do together. It’s also not a closed question, which means they have to give you more than a ‘yes’ or ‘no’ answer. [Read: How to ask someone out over text and get that satisfying “yes”!]

14. “Any suggestions for relieving stress?”

You’re kind of fishing for sympathy here because when someone texts you a question like this, you’re obliged to ask them why they’re stressed.

Either way, you might get some great tips and a conversation out of it! Out of all the conversation starters for texting, this one has potential for a long chat.

15. “What’s the best bit of your day so far?”

This is better than “hey” for sure, and it’s more than “how are you,” which makes it a great text conversation starter. Hopefully, they’ll say that their high point was you texting them but even if you don’t get that reply, you’ll get a longer conversation out of it at least.

16. “I saw your post on Facebook, tell me more!”

Obviously, to use this one you’ll need to have seen something interesting or controversial they’ve posted on social media. Rather than commenting on the post, texting them means you’ll get a more in-depth chat out of it and you’ll get the gossip! [Read: Social media and relationships: The good, the bad, & the ugly]

17. “How was your meeting?”

It doesn’t have to be a meeting, it can be anything they’ve told you about that’s happening that day. Perhaps it’s a job interview, a presentation, a workout, anything. Asking shows that you were paying attention the last time you talked and that’s impressive in itself.

18. “If you could go anywhere in the world right now, where would it be?”

This one might seem random, and out of all the conversation starters for texting we’ve had so far, it’s a little out there. However, the beauty of this particular text is that you can use your imagination. If they ask you why you texted them that question, you can say you were just dreaming of far-flung travel! [Read: Tinder conversation starters – 31 ways to intrigue them instantly]

19. “What emoji would you choose for your day so far?”

This one is fun! If they text you back a sad face, you can then ask what is wrong. If they text you back something joyous, you can ask why their day is going well.

This one has a lot of scope for a continued conversation. Of course, don’t forget to give your own emoji! [Read: How to start a conversation with a stranger & say the right things]

20. “What is your favorite ice cream? Let go get it this afternoon!”

Cute, quirky, and you’re asking them out for a casual date or meet up, so it covers all the basics. You can even text this to someone you’re not romantically interested in, perhaps a friend you want to cheer up. Of course, in that case, you should already know their favorite flavor!

21. “I’m just texting to brighten up your day!”

This is a cheeky one but it’s a fun thing to text someone. It will definitely make them smile even if they don’t want to. Conversation starters for texting don’t always have to lead to deep conversations, sometimes they can just lead to cheeky and even flirty chats. [Read: How to ask someone to hang out over text correctly and have success]

22. “I’m having a boring day, can you tell me a joke?”

Earlier on we mentioned telling a joke, but if you’re out of laughs, why not ask them to tell you a joke instead? Wait for the reply and don’t expect it to come straight away; most people need to think a little before coming up with their best gags. [Read: Use humor to win her over: Funny things to say to a girl]

23. “Let’s play the story game, I’ll start”

If you don’t know the story game, basically one person starts off the story and tell a little of it, then the other person takes over, and it keeps going in that pattern until the story is finished. This is a great way to spend a good chunk of your day chatting. That makes it one of the best conversation starters for texting! [Read: 32 really fun and flirty games to play over text and connect with someone]

24. “I’m in the market for a new cell phone, any recommendations?”

Asking for someone’s opinion on something you’re going to buy is a great way to get a conversation going and keep it rolling. Of course, you might not be in the market for a new phone at all, but they don’t know that. Sneaky!

25. “What is the most spontaneous thing you’ve ever done in the middle of the day?”

They’re bound to think that you’re bored and you want to do something spontaneous and exciting to perk up your day. Nothing wrong with that! It will definitely lead to a deeper conversation and maybe you can both be spontaneous together. [Read: 33 awesome date ideas every couple should try]

26. “Avocados, yay or nay?”

Odd but certain to get a reply! Avocados – you either love them or can’t quite figure them out, right? Find out where they are on the spectrum by asking this question and get the conversation started.

27. “Tell me your most controversial opinion”

The great thing about opinions is that they’re text conversation starters and they’re going to keep it going too! You can agree with them, disagree with them, learn from them. The options are endless.

28. “How did you have your eggs this morning?”

Another cheeky one! Maybe you already know how they like their eggs, but if you don’t, this is a great way to find out!

If you end up spending the night with them one time, you can surprise them with their favorite eggs for breakfast. Jumping ahead a little? Possibly, but it’ll make them laugh at least. [Read: Good morning texts – 50 ways to start someone’s day with a smile]

29. “What smell always brings back memories to you?”

We’ve all been there – you’re going about your day and you smell a particular scent. Bam! You’re back in high school about to take a big test, or you’re in the middle of breaking up with your first love. Smells are powerful and they’re handy ways to start a conversation too.

30. “Your face just popped into my mind, I wanted to say ‘good morning'”

They’ll be pleased you thought of them and you’re greeting them too. Good morning texts are the best, aren’t they? [Read: 20 reasons a good morning text is so important]

Top tips for making the conversation last

It’s not always just enough to get the conversation going. You’ll also need to know how to keep it rolling. Here’s are a few ways you can maintain a great conversation after starting it.

1. A quick clarification on questions

Earlier we mentioned questions. Now, questions are a great way to keep a conversation going after it’s been started, but don’t go over the top.

Really, all you need to do is ask someone to elaborate or ask follow-up questions. The trick here is to not ask too many.

If you’re just asking and asking and asking about something, they’ll feel like they’re being interviewed, which will make them want to stop talking to you. [Read: 40 easy questions to ask your crush to subtly flirt with them]

2. Don’t try to control it too much

Let the conversation go where it’s going. If you started talking about bands and something got on the topic of tattoos, let it be. Don’t try to control the conversation too much because that’ll feel awkward and uncomfortable to the other person.

3. Figure out what they like talking about and expand on it

You can easily tell when someone likes talking about something because their responses will be longer and will seem happier.

Expand upon those things. Ask questions about that topic to keep the conversation rolling in a great direction. [Read: How long does getting to know someone really take?]

4. Be yourself!

Don’t try too hard to be a certain way. Just be you. If you’re trying too hard, it’ll come across in the texts. Talk just as you would with a close friend and you’ll be just fine.

5. Let them start the conversation sometimes too

Don’t always be the driving force of the conversation. Let them hit you up first sometimes. Let them take the lead when it comes to what topic to talk about. This allows for a good balance that’ll seem natural and fun.

[Read: 25 good conversation starters for when you’re drawing a blank]

We know how hard it can be to get a good conversation going when you’re shy or just not great at talking to people. Having some fun and flirty text conversation starters ready to go will definitely make anyone you text look forward to texting you back!

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