How To Start A Conversation Over Text? Tips To Turn You Into A Texting Genius

When we meet someone new, we often wonder how to start a conversation. Or more precisely, how to start a conversation over text. We live in a digital era, and we often meet people online. And that is why you need a good text message that will engage you two in a conversation. And hopefully, a date and something more.

But the first step is to find a way to connect with the new person you meet. You can go a number of ways. You can ask for their number, you can ask for a date, or you can try and see how you two click together.

The good thing is that most text phrases, tips, and rules, work for both men and women. Just tweak them to make them more personal.

With our few simple tips, you can make starting a texting conversation easier than ever. There are lots of icebreaker texts, flirty text, and everything in between.

Pros And Cons Of Texting

Let’s be honest. Most of the new people we meet today are online. We meet them on Facebook, Instagram, Tinder, or some other dating application. And there is nothing wrong with that. Times have changed. Social media took over. Before we get to some tips on how to start a conversation over text, let’s take a look at the pros and cons of texting.

On the plus side, the ease of texting makes it a preferred choice for simple conversations among young people. Texting also allows you to multitask. You can chat with several people at once. You can also watch a video on YouTube and chat on Facebook Messenger at the same time. Just turn that heads thing on.

When used with other forms of communication, texting can be fun, useful, and convenient. But it has to start somewhere.

On the flip side, the negative part is that some conversations are just better off having over the phone or in-person. And the girl or guy you like might not be a good texter.

Generally speaking, we say that if you cannot express something in two sentences, it is a too heavy topic for a text. Just pick up the phone and have a conversation.

With that in mind, here are some ways for how to start a conversation over text.

Give A Compliment

Compliments work perfectly when it is the first time talking to a potential girlfriend or boyfriend. It is a good way to break the ice. For example, “you look great in that (insert color) shirt.”

You can compliment anything you like. Scroll over your potential partner Instagram or Facebook feed, and find something you can compliment. Just do not sound creepy and like a stalker. Don’t look for a picture from five years ago.

Weekend Plans

It is a simple question that will get you two engaged in a fun conversation. Just ask “hey, what do you have planned this weekend”. You get an idea of his/her interests while also engaging in a conversation for a date. If both of your schedules are open, you can get together.

The Low-Risk High Reward Approach

Again, we have a simple question for you. It is, “how would you describe yourself in three words”. It might sound like a job interview question, but it is not. This question gives you maximum insight in minimal characters.


How Do You Relieve Stress?

We live in a stressful environment. Stress is everywhere around us. There is no going around it. And we all have different ways to cope with stress. Ask your crush what is his/her way to relieve stress? Maybe you two have a common interest that helps you fight with everyday life.

What Was Your First Concert?

As you can see, many of these questions try to gauge the common interests you two might have. This question helps understand what kind of a person you are talking to. And hey, you might get into a fun conversation about past music traumas.

What Is The High Point Of Your Day So Far?

When you want to start a conversation, the trick is to ask questions that will let the other person talk. He/she cannot answer with yes or no. That is the blueprint.

So, no matter who are you talking to, ask him/her about the day. But do not just ask how was your day. Be creative. Be different.

Are You Working On Anything Exciting At The Moment?

Here is another question that will definitely put you two in a conversation. It is a great conversation starter. Do not limit this question to professional initiatives. You can work on something creative outside of work. For example, an exciting dinner project.

What Do You Bring With You Everywhere You Go?

There are many questions that help you understand the person you are talking to. This is one of them. We all have things we cannot live without. What is yours? What is your crush’s favorite item?

It helps you understand whether you talk with a pragmatic person who brings only essentials, or someone different.

What Is The Most Interesting Thing You Have Read Recently?

This is another question that will spark interest, fun conversation, and engage you two in a discussion. It can be a book. Or an interesting article. Or anything in between.

Do You Have Any Hidden Talents?

We all have them. You might find out something about your crush’s photography skills, singing skills, dancing skills, or even poker skills.

Make a reference to something they mentioned

If you two have met before in a group, and now you want to start a conversation over Facebook Messenger or Instagram, this is it. It shows you have paid attention to the conversation. Girls love it.

Cliffhanger Text

What do you want to do when a show or movie ends with a cliffhanger? You instantly want to see the sequel, the next episode, the next season, and so on. Right?

Well, the same logic applies to a conversation as well. You can start a conversation and make the other person want more. Just give him/her enough information to pique their curiosity.

The Meme And Emoji Way

This is one of the most common ways young people start a conversation nowadays. Meme works as a great conversation starter. GIFs as well. But do not send thousands of memes and GIFs. Or emojis. Stick to one or two that will gauge interest and pique curiosity.

It is a fun and silly way to show someone you think of them.

If You Could Outsource One Thing In Life, What Would It Be?

For some people, it is cleaning. For others, it is cooking. The list goes on, grocery shopping, driving, studying, walking the dog, laundry, and so on.

The trick here is to ask your partner what would he/she spend that extra time on.

If You Came With A Warning Label, What Would It Say?

Expect a dirty little secret. Of course, if that is a person who is comfortable speaking about it. Not all people are.


What Is Your Favorite Food?

Sometimes, the old-time classic text does it best. It is an old trick, but it will never die. Go back to basics with this text conversation starter. You can continue the interesting conversation by talking about a spot where you had that food. Or a good restaurant that has great cuisine. The options are limitless.

If You Could Travel Anywhere In The World, Where Would You Go?

These types of questions help you understand more about your crush. Sometimes it is a place they have visited before. Or it might be a destination on their travel bucket list. In both cases, you can talk about your travel endeavors.

Teasing Text

If you want to be playful and flirt, you can always go with some teasing text or flirty text. For example, “If I worked where you work, we would get in so much trouble”. Or, “I hope you have a good day. Mine is awful, and I would welcome a hug from you”.

Casually Ask Him/Her Out Question

As we said before, you can never go wrong with basics. For example, “I was just heading out for a drink. If you are interested, let’s go and grab a drink”. Or, “I really want to see X movie tonight. If you are in the mood, we can meet there”

Top 3 Rules For Successive Texting

We talked about some of the ways for how to start a discussion over text. But let’s talk about some of the rules about texting.

Show Your Confident Side

Sending the first text is bold. But it also shows major confidence. It shows you are not afraid of going after what you want. You might feel nervous at the time, but it is fine to text first. But if you want to send a text, do not overdo it. Show you are confident.

If your text shows any hesitation, you are in trouble.

Be Original

Everybody texts this day. And because of that, you have to be a savvy texter. You have to stand out from the crowd. The basics like Hey, Hello, Hi, How are You, do not work anymore.

They are utterly boring and a total turn-off. Most users even ignore a message like Hey.

Ask Open-Ended Questions

We touched on this topic a bit before. We explained some questions that start a conversation. Basically, an open-ended question is one that cannot be answered with Yes or No. These open-ended questions give the discussion somewhere to go. They show interest, and they are not flat and fading.

Here is an example we gave you before. Do not ask “How was your day”. Instead, ask “What was the best part of your day”.

Written by Steven

Steven is a young student from San Francisco who is obsessed with computers.

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