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38 Ways to Start a Conversation Over Text & Make Each Text Fun to Reply

You’ve got their digits, but what now? You need to be witty and entertaining, but first, you need to learn how to start a conversation over text. 

how to start a conversation over text

Getting to know someone over text is hard. It’s tedious and if you don’t get the conversation moving in the right direction, you’re out of luck. Knowing how to start a conversation over text so you don’t bore the person you really like can help you land that special someone.

If they’re always bored talking to you via texting, they won’t want to risk hanging out in person. They’ll see that you don’t have anything to talk about and they won’t want to waste their time on someone boring! [Read: How to not be a boring texter and keep your crush really interested]

Why good conversation always leads to a great connection

You may not think that what you say over text will make someone like you more, but it will. When you say all the right things – and all the honest things – it helps someone get to know you better.

You build up a banter that creates chemistry and when someone feels that chemistry over the phone, they’ll be really eager to meet in person and hang out with your often. That’s why learning how to start a conversation over text is so important.

Not to mention the fact that great conversation opens the two of you up to each other. When you get talking, you learn a hell of a lot more about a person than you would if you just sat across the table from them and asked question after question. [Read: How to flirt over text and type your way into someone’s heart]

How to make conversation over text and appear exciting and fun

In order to avoid boring your crush to death, you’ll want to pick up a few pointers. Here’s how to make conversation over text exciting in a way that’ll draw their attention and keep it on you.

1. Avoid typical greetings

“Hey, what’s up?” is not a great way to start a conversation. It seems innocent enough but they probably always get texts like that. In order to seem different and better than the others, you need to be unique.

Instead, start with something relevant to them. Something like, “Can you believe that last episode?” when referring to a show you both watch can be more than enough. Use these 25 really fun and cute ways to say “hi” in a text message and be more interesting to give yourself a great head start!

2. Begin with a question

As we mentioned above, starting with a question is a really powerful way to get someone’s attention. Not only are you bypassing the boring way to greet them, but you’re texting them with a purpose. It’s one of the best ways to learn how to start a conversation over text.

It also makes them feel a hell of a lot more important, and when you make someone feel important, they like you more!

3. Don’t be afraid to dig deep

Don’t stick to casual conversation. If you want to know more about them, just ask.

You can easily transition into some deeper questions just by saying something like, “Someone asked me about my least favorite part of childhood and I was wondering what yours was? Mine’s not being able to eat what I want, when I want! Sksksksk.”

This is super simple, but it also reveals something about yourself while kickstarting a new conversation. They’ll feel more comfortable sharing something about themselves once you already have. [Read: How to open up to you so you can really connect]

4. Focus on the real conversation

There are a lot of people who focus on getting the other person to like them by asking a bunch of questions about them one after the other.

This is not the way to get someone’s attention over texting. It’ll just seem like an interview.

When the conversation is going and it’s pretty smooth, don’t halt it just to ask a question. Let things progress naturally. [Read: How to not be a dry texter – Signs you’re one and the best quickfixes]

5. Use some emojis when necessary

If you want to make your conversations a little more exciting, use some emojis!

Nothing gives a text conversation personality like a well-placed emoji. Use it to show emotion and make it fun and silly. Your crush will appreciate it. [Read: 20 flirty emojis that’ll make you a pro flirty texter in no time]

6. Let go of dead conversations

When a conversation is done, it’s done. Stop trying to revive it.

You’ll only make things awkward and they’ll be bored with the whole thing since they clearly don’t want to talk about it anymore. Just let the conversation end when they do and start up a new one!

7. Talk about things they enjoy

If you know what they like to do, then start talking about it. People love chatting about what they’re passionate about. If you know they love painting, talk about that!

Ask what type they like, why they like it most, or who their inspiration is. Not only will they be grateful for you wanting to know about what they love, but they’ll also never forget how invested in their passion you were. [Read: 20 intellectual conversation topics that ignite meaningful communication]

8. Avoid short replies

Just stop with this. If you want to learn how to make conversation over text, you actually need to have a conversation.

If you just send back, “cool,” when they talk about something, there’s nothing for them to work off of. You’re basically stopping the conversation right there. [Read: Dry texting and the real meaning behind those dry one-word replies]

9. Ask follow-up questions

When you’re in the middle of a conversation, the best thing you can do is ask follow-up questions about their response.

If they tell you their opinion on something, ask how they came to it. It’ll keep the conversation going and also show them how invested in it you are – and how much you care to hear what they think. [Read: 60 fun and deep get to know you questions to peek into their soul]

10. Talk about controversial issues

You may need to be careful with this one but if you do it right, you could have a great conversation that lasts a long time.

You never want to talk about something that might offend them, but talking about semi-touchy topics will always make for great conversation. Just be prepared for some friendly arguments. They can even be great. [Read: How to have playful banter and keep the naughty flirting alive]

11. Avoid cliché topics of conversation

Nobody likes talking about the weather. Unless you have a crazy story about a storm that just went by, don’t talk about the weather.

Make sure your conversations are unique and not something they could be talking about with anyone else.

12. Use their social media to your advantage

You have permission to creep on their social media, that’s right! You can get a lot of great ideas for conversation right from their feed.

If they share a post about something and have a strong opinion, you can bring that up. They clearly enjoy things on their social feeds so use what you can to get their attention. [Read: Social media and relationships – The good, the bad, and the ugly]

13. Send them memes you think they’d enjoy

Memes are always fun. And making your crush laugh will definitely earn you brownie points.

Send over some funny memes and wait for their reply. Just make sure not to overdo it or send too many at once. [Read: How to be a fun texter and make them laugh while reading your texts]

14. Pay attention

Pay attention when they’re texting you. Notice what things they seem to talk a lot about and tailor your conversations to other similar things.

In order to know how to make conversation over text, you need to know how to pinpoint what matters most to them. [Read: How to be a better listener and pay more attention]

15. Don’t overthink everything

When you sit and think about what you’re going to say and go over every word multiple times, you’ll panic. It’s not necessary. Send what you feel and keep the conversation genuine. If you try too hard, it’ll show.

Easy and fun questions you can ask to make conversation over text

Now that you know some of the basics of how to start a conversation over text, let’s dive deep and give you some really specific ideas for how you can get a conversation going – and keep it going – over text. Here are some questions you can ask to make conversation over text.

1. If you were on death row and had one last meal to eat, what would it be?

This is a fun question, but it also will let you see what kind of eater they are. If they say fast food, then you know they are a fast food junkie.

If they mention something more exotic like Indian food, then you know they aren’t a picky eater. Either way, it will help you figure out what kind of restaurant to take them to on a date in the future. [Read: 20 flirty texting facts to help you have a good love life]

2. If you won the lottery tomorrow, what would you spend your money on?

You can see a lot of this from this question. First, you can see how materialistic the person is. If they say they would buy a mansion, diamonds, fancy cars, and yachts with it, then you know they are into material possessions.

But if they say they would donate a lot to charity help others, then that shows you a different set of moral and priorities. You can also see if they are more of a spender or saver, because they might say they would invest it in the stock market. [Read: Texting anxiety – How to send and receive texts without freaking out]

3. Would you run 5 blocks, naked, in broad daylight in a major city for $1,000,000?

The answer to this can show a few things. First, are they shy about their body? Or are they adventurous and would try just about anything? Some people like crazy activities, and some would never, ever do it.

If they say no, keep probing and ask how much money it would take for them to do it – if any. Also, ask if they would do it if they had a paper bag over their head so no one would know who they are. [Read: 40 sexy and naughty would you rather questions that’ll make anyone horny]

4. If you found out that your parent, sibling, or best friend was selling national secrets to our enemies, would you turn them in?

This question will let you know how loyal they are to their loved ones. It’s kind of a tricky question because on one hand, if they turned them in, it shows that they are loyal to their country.

But if they wouldn’t turn them in, then they are loyal to their loved ones. Either way, the meaning behind that is up to you. [Read: Am I texting too much? 16 signs they think you area clingy texter]

5. Do you believe in ghosts or evil spirits?

This question will help you get a feel for their spiritual beliefs. You might find out that they are an atheist and don’t believe in spirits. Or you might find out that they believe in the devil and evil.

After discussing that, you can probe deeper and ask if they have ever seen a ghost or had any encounters *or know anyone who has*. Or if they would stay in a house that was supposedly haunted.

6. Do you think that marriage is necessary to have a family?

Even though marriage is still common these days, some people believe it is not necessary. If the person you are trying to make conversation with over text is someone that you think you would want to date long term, this is an important question.

It’s important to be on the same page with each other on values like that. But if it’s early in the relationship, try to de-personalize it. Don’t bring the “we” into it. Just keep it objective. [Read: Texting etiquette and flirting – 26 rules guys and girls must follow]

7. If scientists discovered a cure for cancer, but it automatically killed 10% of the people who took it, would you want it to be released to the public?

This would lead you to an interesting philosophical discussion about the value of life. Of course, we all value life.

But this kind of question allows you guys to wrestle with the question of whose life is more important – the ones whose lives are saved or the ones who might be killed by the drug? There are a lot of implications from this question that could be taken even deeper.

8. Do you think aliens exist or are we alone in the universe?

The concept of alien life and whether it exists is a great way to see how deep of a thinker the person is. Sure, we’ve all thought about aliens because most people have seen movies about them.

But you can ask a lot of follow-up questions to see how much they have actually thought about the topic. You can even have a little debate between the two if you if you have differing opinions. [Read: Lack of communication in a relationship and why it signals the end]

Who are you texting? How to change your conversation depending on how well you know them

Now you have an overview of the subject, how to start a conversation, and a few fun but long-winding questions to start a conversation over text, there is something else you need to know.

There is no one rule or method that applies to everyone you may be texting. If you’re texting someone for the first time, it will be different than starting a follow-up conversation or chatting up a friend.

Before going in with a pickup line or dirty joke, take into account how well you know this person and what sort of conversation will feel natural. [Read: How to not be a boring texter and keep anyone you chat with interested]

1. Are you texting someone new? 

When it comes to knowing how to start a conversation over text with someone new, that is probably the most challenging. If you didn’t meet at school or work, you may not have anything in common to offer a reason for reaching out.

Be unique. Instead of starting with a “hey, what’s up?” try something that makes you stand out a bit. If you’re hoping to make a plan out of this conversation, maybe something like…

“Hey, it’s *your name here*. I had a great time meeting you the other day. There’s a new restaurant opening around the corner from me. They’re supposed to have the best cheese fries if you’d like to go sometime.” [Read: How to ask someone out over text and get that satisfying yes]

2. Just want to talk?

If you’re texting someone new, but don’t want to commit to meeting up, try something more playful and interesting to get a conversation going.

Even something as simple as, “I was watching The Office, and something Michael Scott said reminded me of the other night.”

Adding a glimpse of your hobbies or interests into your first text will give them something to latch onto to carry on the conversation. It can also welcome follow up questions. Say you mentioned just getting back from a weekend away, you can then talk about traveling. [Read: 40 questions to ask your crush to subtly flirt with them]

3. Are you texting someone from work?

If you recently got a mutual friend’s number, say a coworker or peer, reaching out should be easier. You have common ground to walk on, so to speak.

You can go in asking about a work project, clarifying something your boss said, asking for some notes you missed, or even bringing up something a mutual friend said.

This all makes starting a conversation a bit less nerve racking. It shows you have a reason to reach out on top of just wanting to chat. [Read: How to not be a boring texter and keep anyone interested]

4. Can you woo a friend?

Probably not with one text, but with a series of fun and flirty conversations… maybe so. If you have a crush on a friend of yours, avoid texting them the same way you normally would. That will only push you further into the dreaded friend zone.

Try something subtly flirty. Even a simple compliment like, “You looked great yesterday,” puts a less platonic spin on the conversation.

You can also go for the go-to, make them laugh. Try a meme or link to a funny article.

Or you could come all out and make it obvious that you are looking to advance your friendship. Send them a BuzzFeed list or quiz about being stuck in the friend zone and see if they pick up on that less than subtle hint. [Read: How to text flirt with a friend and subtly seduce them]

5. Want to reach out to the person you’ve been dating?

Knowing exactly how to start a text conversation with the person you have only just begun dating can be confusing. Do you go straight in all comfy like you’re official with a “Hey, babe?” Or do you hold back? 

No matter what, never say, “Sorry if I’m bothering you.” This message in and of itself is bothersome and annoying. It shows you have a lack of confidence and question this person’s interest.

So even if they say something like “sorry, busy right now.” Respond with a “No worries, talk later.”

You want to remain confident, but not too enveloped or else you can come across as a little needy. Start with a question regarding something you’ve discussed before. Ask how that meeting at work went or if their mom had a nice birthday. This not only shows you listen but are invested in their life too. [Read: How to keep a text conversation going when you have nothing to say]

6. Want to reach out after a fight?

Sending the first text after a fight can be awkward. You don’t know if the anger has blown over. You aren’t sure if you can go in with humor or how exactly to measure the situation.

If you want to start a text conversation after a fight, whether big or small, an apology is a great place to begin. It doesn’t have to mean you admit you were wrong, but just that you feel bad that you fought and want to work it out. [Read: The first fight in a relationship and what to do next]

7. Can you start a conversation after radio silence? 

Just like texting someone new, starting back up after weeks, months, or even years of not talking can easily go array. Either the person won’t answer, will be curious where you’ve been all that time, or will actually want to talk.

The best way to go about this is to come straight out with the facts instead of trying to hide it. Saying something like, “Hey, I know it has been a long time since we talked, but I wanted to see how you are” is a great place to start.

You could also start this conversation with an old picture you may have found or reboot news on a TV show you know they love. Anything that would show that something reminded you of them will feel more natural.

8. Trying to reach out to someone who is ghosting you?

This is something I’ve researched a ton in my younger years. Wanting to talk to someone who is ignoring you is part of human nature. You want to know what you did wrong or why they ghosted.

Will they apologize? Will they ignore the fact that they’ve been so rude? If you are trying to do this, I’m sorry, but don’t. We know you didn’t want this answer, but it isn’t worth it. If this person can’t send a simple text, they aren’t someone you’d want to date or have in your life. [Read: Being left on read – what it means when they don’t text back and what you need to do]

9. Do you feel guilty for ignoring someone?

If you were the ghoster and feel badly for being so rude, starting a text conversation can be awkward. Now, the fact that you feel bad is a good thing. It shows you have a heart, unlike many people who ghost.

If you genuinely feel bad and want to start talking to this person again, own up to it. Say that you are really sorry for ghosting them and hope they’ll give you another chance. Don’t make an excuse or try to avoid what you did. They know and you know.

10. Are you trying to reconnect with an ex?

We very rarely promote this. There is a reason your relationship ended. You may miss things right now, but that is because you’re not together. Unless you have both fixed the issues that broke you up in the first place, it isn’t a good idea.

If we can’t talk you out of it and you’re going to do it anyway, try this… Be honest about why you’re reaching out. Don’t be shy. Don’t act like you just thought of them.

If you want to hook up, come out with it. If you want to pick up something you left at their place or have recurring feelings for them, be honest. There is no point in wasting time beating around the bush. [Read: How to text your ex after no contact and not make the same mistakes again]

11. Do you need something?

If you want to talk to someone because you need a favor, you have to have a balance of kindness and bluntness. Learning how to start a text conversation when you need something is about subtlety.

Be kind and ask how they are. Have a genuine interest in how they’re doing. Don’t wait too long to ask for the favor. This will come off like you’re using them.

Ask for the favor and offer something in return at the same time. Don’t say, “I’ll owe you one.” For example, “I could really use your help moving my couch this weekend. Pizza and beers are on me.” [Read: Are you a user? 15 uncomfortable facts to help you face the truth]

12. Are you lonely?

If you want to talk to someone because you’re lonely, don’t text someone that could reject you. Don’t reach out to someone that has ghosted you before.

Don’t start a conversation over text with an ex or someone you’re in a situationship with. It will leave you feeling worse.

In this case, text a trusted friend, sibling, or even a parent. They will be able to cheer you up and keep you company, even digitally. [Read: Why do I feel so alone? The answers that can change your life]

13. Do you have a topic in mind?

If you already know what you want to talk about, there is no need for niceties. You don’t need to go in with small talk. It is texting, not a work email.

If you want to talk about something awkward that happened or ask a sensitive question, do it. You can preface it with something like, “if you have the time I’d like to talk about something…” This lets them know you want their attention.

But, then jump into it. [Read: Why being blunt can be a great asset]

14. Is it worth it?

If you want to start a text conversation with someone you don’t like, just to fill the time, is it worth it? Are you trying to text someone who always gets under your skin? Why? What will be different this time?

Ask these questions before starting a text conversation, especially with someone that isn’t close to you.

15. Are you still too nervous?

If all else fails, a wrong text fake out is slightly immature, but still a less risky way to go. If you’re scared of rejection or ghosting you can say something you would text a sibling.

Something like, “we’re out of milk,” or “I don’t know, ask mom.” They’ll know this text isn’t for them, but it can be an entryway into a new conversation. [Read: The accidental text on purpose – How to use it and when to avoid it]

Now you know how to start a text chat, it’s time to get to it

You now have all the information you need to not only start a conversation over text but keep it going, what are you waiting for? Push aside your nerves and get to it. You never know, maybe it could lead to a full-on conversation in person pretty soon!

[Read: 12 clever text messages to get anyone to text back right away]

Knowing how to start a conversation over text is pretty much a must-have skill with the way dating works in this age and time! Follow these tips and just send out your first text, it’s easier than you think!

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