23 Ways to Make Conversation Over Text So You Never Bore Your Crush

When you like someone, how do you find interesting things to talk about if you’re not face-to-face? Here is how to make 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 make 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.

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. [Read: 25 really fun and cute ways to say “hi” in a text message and be more interesting]

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.

And that 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: 20 meaningful topics that ignite deep conversation]

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.

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.

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.

Questions you can ask to make conversation over text

Now that you know some of the basics, 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: How to keep a conversation going with the opposite sex]

In order to make progress with your crush, you need to know how to make conversation over text, and good conversation. These tips will help you stand out from the crowd and get their attention.

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