How To Keep A Conversation Going Over Text?

If you like talking to someone, you might wonder how to best interact with them. On the one hand, you don’t want to come across as awkward or clingy.

But you have also probably realized texting sometimes feels safer than talking face-to-face.

Whether you’re talking to a potential romantic interest, best friend, or colleague at a new job, practicing optimal text etiquette is important.

Here are the best ways to make the most of your text conversation:

Tips for When You’re Texting Someone You Like Romantically

Are you trying to connect with someone you really like? Texting is an easy way to get to know someone, strengthen a relationship, and have meaningful discussions. Likewise, it’s fun and often feels less intimidating than talking on the phone.

But if you have trouble keeping conversations, the other person might lose interest before they even get to know you.

Here are some tips for making the most of your text conversation:

Ask the Right Open-ended Questions

Any qualified relationship expert will tell you this: if you want to keep a conversation going, make sure you ask the right questions.

A close-ended question can be answered with a simple one-word ‘yes’ or ‘no.’ For example, “did you go to that job interview today?” is a close-ended question. There usually isn’t much room for further discussion.

Open-ended questions help keep any conversation flowing. So, instead of that first question, you might instead ask:

  • “Hey, how did that interview go today?”
  • “You met with the directors today, right? What did you think?”
  • “I was thinking of you during that interview. How was it?”

These open questions exhibit genuine curiosity and invite further discussion. And. the more open-ended questions you ask, the more your conversation will flow.

Talk About Yourself

Don’t respond with one-word answers yourself! If you want to start bonding with someone, you need to open up and keep things interesting.

So, for example, if someone asks, “how are you?” don’t just respond, “Good.” Instead, consider responding by genuinely answering the question. For example, you might say, “I’m feeling a little tired today. Had trouble sleeping last night. But I’m hanging in there. What about you? How are you doing?”

Reference a Previous Conversation

Did they mention their favorite restaurant to you in passing the other night? If so, you have an easy reference point. For example, you might say, “Hey! I’m considering going to that place you mentioned loving for dinner tonight. What should I order?”

This approach keeps the conversation flowing and shows that you’re interested (and paying attention) to previously referenced discussions. Bonus points if you can somehow tie in an inside joke with your text!

Flirt Appropriately

Flirting is both an art and a science, but many people find that technology makes it easier to practice this important dating skill.

As a first step, you want to start slowly. How comfortable do you feel with this other person? Have they been flirting with you?

Some general flirting tips include:

  • Send compliments: Everyone loves to feel praised. Something like, “I loved spending time with you today,” or “You’re amazing!” can go a long way.
  • Use emojis: Most people agree that emojis can help intensify a text conversation. Don’t be afraid to throw in the heart, kissy face, or evil face to convey your thoughts.
  • Don’t ever send unwanted nudes: Not only is this inherently dangerous (photos can be saved forever), but many people find them offensive and rude.
  • Keep hinting about being interested: It’s fun to be sly. Questions like, “do you want to know what’s on my mind right now?” can drive someone wild.

If you two have been flirting for some time now, consider sending more romantic, longer messages. But don’t jump into those immediately- they can come across as too forward.

Find Common Ground

If you’re just getting to know each other, asking questions that help you learn more about their preferences or interests is helpful.

Finding common ground makes it easier to have a good conversation. You can start with easy, surface-level topics like discussing a favorite movie or food. Knowing their interests can help you feel more connected, and it can keep the conversation going.

Send Pictures, Memes, or GIFs

If you want to keep the conversation light, consider sending a funny meme or image to the other person. Decide whether or not providing any additional text is necessary (many times, it isn’t!). But you may want to say something like:

  • “I saw this earlier, and it totally made me think of you!”
  • “Doesn’t this remind you of what we discussed earlier?”
  • “What’s your reaction to this meme?”
  • “Haha dying at this!”

Bring Up Something You Saw Them Share Online

Are you feeling a lull in the conversation? Consider referencing a recent post or story they shared. This makes things more personal than simply commenting or messaging them about it on social media.

Of course, if you plan to do this, you want to establish a baseline relationship first. If you barely know the other person, this forward approach may come across as invasive.

You certainly don’t want someone thinking you spend your free time stalking their social media.

Know When to Stop Responding

At some point, a conversation needs to have a natural break. You don’t want to intrude on someone’s personal time or pressure them into responding.

And if you sense that the other person is pulling back, pause before sending more texts. If someone likes you, they’ll want to keep the conversation going. If someone’s having doubts, they’ll naturally withdraw.

But, as a general rule, don’t just stop texting someone to get their attention. People who care about you will notice your absence, but they’re likely to worry they did something wrong- or that you’re upset with them. It’s much better to be upfront if that’s actually the case.

However, you might want to cut down or pull back your texts if:

  • they keep responding with one-word answers
  • they take several days or weeks to get back to you (without a reason why)
  • they never ask you questions about yourself
  • they seem annoyed or bothered by your texts

If this behavior emerges from nowhere, it’s worth asking if something happened. You very well may have done something that bothered them. If that’s the case, be sure to listen closely and learn from your mistakes.

But if they are vague or relatively non-responsive, it may mean they are either too busy or no longer interested (but aren’t willing to be assertive in their response).

Tips for When You’re Texting Friends

Making friends is hard, and maintaining those friendships can be even more challenging. Good relationships require ongoing maintenance.

Fortunately, texting makes it easy to connect with one another, no matter how busy your lives are or how far apart you live from one another.

Text Them Regularly

Try not to go too long without connecting. In fact, it may be helpful to tell your friends that you want to make a genuine effort to stay close.

Keep track of their birthday and other important dates on a calendar or stored in your phone. That way, you can reach out and send some kind words when that time comes.

Reach Out If You Sense They’re Struggling

Are you concerned that your friend is going through something? Does it seem evident they had a bad day?

Reaching out over text shows you care and are there for them. You can send a message like:

  • “Hey, I just want to let you know that I’m thinking of you. I’m here if you ever need anything.”
  • “I know you’re going through a lot right now. Are you free for coffee this week to catch up?”
  • “I’m picking up dinner right now. What can I drop off for you?”

Don’t pester someone to send a response right away. If your friend really is going through something, it may take time for them to collect their thoughts and reach out. But sending them a kind text shows that you’re ready for them the moment they text back.

Keep the Conversation Light

Aside from those more serious moments, friends generally use texts to connect with one another. Keep the conversation going by sharing funny pictures, inspirational quotes, or updates from your day.

Use Texting to Solidify Plans

Ultimately, nothing beats face-to-face conversation when it comes to meaningful friendships. You can text each other all day long. But you should use these conversations to try to make real-life connections.

Fortunately, texting makes it so easy to make and concretize plans. You can start by sending a simple message like, Hey, I haven’t seen you in a while. What are you doing this weekend? Would you like to meet up for lunch?

This is one area where closed questions may be more beneficial. Your friend has to either accept or decline your invitation. It’s much more efficient than saying something like, “We should hang out soon! I miss you. What are you up to?”

Tips for When You’re Texting Coworkers or Bosses

Text etiquette takes a different turn when it’s for professional purposes. Nowadays, many employees are also expected to interact with their team through texts (along with emails, Zoom calls, or Slack messages).


Don’t Act Like You Are Friends With One Another

Sometimes, loosening your style when texting with coworkers or bosses is tempting. This is especially true if they’re acting casually with you.

But remember: you never know what can be used against you. And any response stays documented.

So, when in doubt, assume you’re being treated as if you’re in an important meeting.

Always Proofread Your Texts

We’ve all heard of autocorrect fails, and you don’t want to send a ridiculous text to your boss! Before you send anything, give it a quick read. Ensure you don’t say something you wouldn’t say in person!

Use Appropriate Spelling and Grammar

Even if your colleagues or boss are acting casually, it’s still a good idea to consider your professional reputation. That means using complete sentences with proper punctuation.

After all, you’re interacting within a professional context, and you don’t want to lose credibility for how you write something.

Maintain Work-Life Boundaries

Unfortunately, it’s becoming increasingly common for employers to expect their employees always to be available. And you sending quick responses- even when you’re having dinner with your family or enjoying your weekend- only enables that behavior.

Unless it’s truly part of your job description, it’s worth reconsidering your separation from your professional and personal identity. Whatever is being discussed can often wait until an in-person meeting the next day.

Your work should have a protocol in place for managing true emergencies. If they don’t, you should consider broaching that conversation with your employer.

When You’re Texting Someone You Don’t Know Very Well

Do you want to keep a conversation going with someone new in your life? Maybe it’s a new neighbor or friend of a friend.

Or maybe you’re trying to solidify plans with a professional (like a house cleaner or painter). Here are some strategies to keep in mind.

Remind Them of Your Name (And How You Met)

Even if the other person saved your number, that doesn’t mean they’ll automatically remember you. And if they don’t recognize who’s texting them, they might not answer.

So, when texting someone new, consider an opening line like, “Hey! It’s (insert name). We met earlier today. Wanted to reach out to you about (insert topic).”

Start Slowly

When you’re talking to a new person, you don’t want to overwhelm them. At first, focusing on being a better listener than a talker is often helpful.

Ask open-ended questions, but don’t ask too many in a row. Wait for the other person to answer before sending another one.

Be Mindful of Jokes or Sarcasm

People often connect over humor, but texting can sometimes make it hard to distinguish a serious tone from a funny one.

When in doubt, try to avoid snark until you know someone better. You don’t want to come across as offensive, and you don’t want the other person to guess your intentions.

Show That You’re Paying Attention

If you’re trying to form a new friendship with someone, you want to convey your interest in getting to know them. This entails actively listening when they talk (or text) and paying attention to the details they tell you.

For example, you might say, “I started that TV series you discussed last week! Thanks for the recommendation. I really like it so far.”

From there, you will probably learn more common interests. That will allow you both to ask and answer open-ended questions to one another.

Don’t Blow Them Up

As much as possible, try to avoid reaching out multiple times in a row before the other person answers. Doing so often comes across as intrusive and annoying.

Be Considerate of Usual Sleeping Schedules

Maybe it’s okay to text your best friend in the middle of the night. But are you making plans with the new neighbor who just moved in? Consider that they might not silence their notifications, and your text may wake them up.

What’s the Best Group Text Etiquette?

Individual text conversations have their own standards. But when you’re texting within a group, you also want to keep some general considerations in mind:

Don’t Just Talk to One Person Directly

If a conversation feels like more of a one-on-one discussion, take it off the group platform. If you don’t, other people will likely feel annoyed or awkward. Or, they may even chime in to express their feedback.

Don’t Start a Group Text Conversation With People Who Don’t Know Each Other

Have you ever been looped into a group text with a bunch of random numbers? It’s a little weird. You’re not sure if you should make small talk or get to know the other people. If someone you don’t know poses a question, you might wonder if it’s appropriate for you even to answer.

So, with that in mind, try to avoid initiating this kind of conversation yourself. The only exception is if you’re trying to plan a specific event to which all the people on the chat thread are invited (or participating).

Always Give Others a Chance to Respond

If there’s one rule to follow, it’s don’t monopolize the group text! This isn’t a place for you to vent or pretend that everyone wants to know your innermost struggles.

Give everyone a chance to share their insights and keep the conversation going. And if you do realize that you’re the only one talking, give it up for a while.

Keep the Conversation Light

In most cases, group texts aren’t meant for heavy, serious discussion (unless that’s the intended purpose of the text). Don’t make things intense unless they absolutely need to be.

Don’t Start a Second Group Chat

Some people start a second group chat to essentially keep secrets or gossip about people in the first group chat. This behavior is rude, and you risk sending the wrong message to the wrong thread.

Most people don’t want friends who behave that immaturely. And if your friends already do this, it may be time to reevaluate your priorities with them.

Other Universal Texting Considerations

No matter who you’re texting, there are some practical rules to consider when starting, ending, or maintaining a conversation.

Consider When to Facetime or Call

Don’t underestimate the power of switching up your communication in a world that thrives on texting. A recent study found that real companionship occurs over the phone or through video, even if it is awkward. Voice, in particular, seems to strengthen intimacy.

In addition, you’re able to have a more in-depth conversation when you’re actually speaking to someone. Even the best text conversation can create problems. For example, you might assume that if someone doesn’t respond immediately, they’re upset or withdrawn.

It can also be hard to interpret a single message’s specific tone and context (are they being sarcastic or actually mean?).

In general, it’s a good idea to consider a voice-based conversation when:

  • you’re in a dire emergency
  • you want to talk about something serious
  • it’s a complicated subject, and you don’t want to spend paragraphs explaining it
  • you’re sharing bad or surprising news

That said, most people actually prefer if you ask to call them. So you might reach out with a text like:

  • “I want to talk to you about something important. Is now a good time to call?”
  • “It’s too much to text right now. Want to FaceTime?”
  • “Okay if I call you later? It would be easier to talk about this over the phone.”

Be Patient

Life gets busy, and you don’t want to hound people to respond when unavailable. In addition, some people need time to formulate their thoughts before reaching out.

But if a few days pass and you don’t hear anything, it may be reasonable to reach out. Say something like, “Hey, I haven’t heard from you lately. Just want to check in and see if things are all right?”

Outweigh the Pros and Cons of ‘Read’ Receipts

In general, most people turn their read receipts off. We usually don’t want others to know when we’ve viewed a message, particularly if we choose to ignore it or respond to it much later. There’s an inherent social pressure that comes with leaving the receipts on.

Some people argue that it’s better to turn on the feature. Why? Because it shows a sense of respect. It also may motivate you to respond to people faster instead of waiting days or weeks to get back to them.

Use Voice Messages With Caution

Voice messages are like a hybrid between voicemails and texts. They can help explain more complex ideas. But they can also come across as annoying or even conceited.

As the first rule of thumb, you should consider the intent. Are you sending audio because you hope it will satisfy your need to talk about something? Or are you considering what’s best for the other person?

Most people find that it’s easier to skim through a text on a busy day than stop what they’re doing to listen to a voice message.

If you’re unsure of the best option, it’s probably best to text someone and say, “I have to talk about something too long to text. Let me know a good time to call!”

Try to Avoid Fighting Over Text

Although it may seem easier and safer than hashing it out in person, it’s almost always better to avoid fighting when you text someone. Why?

Because it’s easy to get swept away with your words and be “brave” behind a screen, but that makes it also likely for you to say something you will later regret.

You can’t really have a texting argument on equal footing. For one, you might share a bold opinion, but you still have to wait for the other person to get back to you. This may keep you in limbo, which can increase frustration and anxiety.

Finally, remember that texts aren’t necessarily private. If you and your friend, for instance, start arguing, they might send screenshots to the rest of your friends. Suddenly, a private conversation becomes this massive, public affair.

If the other person is initiating the argument, you can intervene with them by:

  • telling them you’d like to discuss the matter in person
  • acknowledging whatever happened today (or the day of the conflict) but reinstating that you need time to process it

Let Someone Know When You’re Stepping Away

If you are involved in a serious text conversation, avoid leaving the other person hanging.

For example, if you’re getting ready for bed, send a quick message letting them know you’ll be going to sleep soon. Or, if you’re at work, remind them that you’re busy and may not get back to them immediately.

Final Thoughts

All relationships find their natural flow when it comes to communication. Some people, for example, truly enjoy texting each other daily.

They have no problem giving minute-by-minute updates. Others have no problem just checking in periodically to see how the day is going.

And keep in mind that not everyone likes to text! Some people really do value all that comes with face-to-face interactions- body language, eye contact, and all.

There isn’t a perfect way to have these virtual conversations. But try to keep them fun, interesting, and engaging. If someone likes you, you’ll make the text conversation work!