How To Keep A Conversation Going: 20 Clever Tips For Texting

Good conversations are the key to healthy relationships. If you wonder how to keep a conversation going over text, this post will help. Not everyone is a great conversationalist. Some struggle to come up with new ideas and keep the conversation going.

However, everyone can improve their communication skills with deliberate efforts. If you want to talk your way to a person’s heart through text, this post is for you. Read on.

In This Article

20 Tips To Keep A Conversation Going Over Text

1. Keep the conversation two sided

If you are constantly talking about yourself or topics of your interest, you might be considered selfish. Instead, figure out their likes and dislikes and offer topics to your partner to keep the conversation flowing. For instance, if they like the sitcom Friends, ask questions like, “what is their favorite episode in Friends?” Wait for their response and respond back quickly.

2. Have a unique style of texting

Developing your creative style of texting is the key. Try not to be too formal, at the same time, respect them. You may use emojis, but don’t overuse them. You can text them, “Good morning, hope you have a wonderful day!” to make them feel elated. You may also use some humor to keep the text light.

3. Make them feel special

When chatting with your partner, exchange compliments and show appreciation. Instead of talking about yourself, ask them about their day or things they find interesting. For instance, you could say, “How did you sleep? I’m sorry you had trouble sleeping, but I really enjoyed our conversation last night.” It will make the conversation more special for them and encourage them to keep talking to you.

protip_icon Do remember
Before initiating a conversation over text, be clear about your intentions. Do you want to build a strong connection, or do you want someone to just talk casually? The clearer your motives are, the more open you can be about them.

4. Pay attention to details

Before sending the text, proofread that message to ensure it is correct so that you don’t embarrass yourself with grammatical mistakes or spelling. Ask follow-up questions and talk about their emotions to let them know that you are all ears to what they have to say.

5. Stay relaxed

When nervous, you might make mistakes while texting. Do not pretend to be extra cool or act like someone else. Don’t be in a rush, take time to type, and maintain a good flow. Relax and go with the flow.

6. Be yourself

If your texting style is being sarcastic, go with it. They will get used to it. Also, do not use too many short forms so that they misunderstand you. For instance, instead of texting ‘brb,’ say ‘Will be back in a few minutes.’

7. Know when to close the chat

If you feel that the conversation is going to end, give clarity. Don’t abruptly leave the conversation; instead, inform them. It would be a good way to keep the conversation going later. It also eliminates any confusion or anxiety for the other person when they see you aren’t responding.

8. Use past conversations

If they have spoken about their pet being ill last week, ask them how it is now. They will know you are paying attention to the small details, which keeps them interested and the conversation alive.

9. Be light over text

People only stick to things that make them happy. So keep the conversation light and fun and make them feel positive throughout. For instance, you may talk about your day, discuss hobbies, or tell jokes. Give engaging replies to maintain a good flow of conversation.

10. Stop multi-texting

Sending a dozen messages in a row isn’t a good idea. It can make them feel you are needy. At the same time, if they send you too many texts, be open and clear instead of coming to conclusions.

11. Be patient

People work and have their life with friends and family, so do not expect quick responses. Give them time, check in frequently and don’t come up with wrong assumptions. Instead, remain positive and give them enough space and time to respond back to your texts.

protip_icon Did you know?
Studies suggest that people who are highly emotionally reactive and use text messaging often feel rejected and experience deep anxiety when they don’t see immediate replies to their messages (1).

12. Use memes

Memes are a great connection-building way

Image: IStock

Memes are a great connection-building way to keep the conversation going. If you want your conversation to be fun, give engaging replies. Send them a meme that is funny and repeatable, and wait for their reply. It is the best style to keep the conversation from dying out.

13. Surprise them with a call

Some may think phone calls are old-fashioned, but it is easier to keep the conversation going. Rather than typing an essay to them, surprise them with a call and make them feel special.

14. Don’t answer with one-word

If you are interested in someone, why reply in one word? Instead, drop that habit and send them proper text messages and ask open-ended questions and make it engaging. Acknowledge their response and compliment their views by sharing your thoughts.

protip_icon Quick tip
If you are the one receiving one-word texts, stop texting for a while and see if they care to text you back.

15. Talk about life

It doesn’t mean you need to be philosophical, instead talking about each other’s lives would help you get to know about each other’s lives. This can be a good way to keep the text conversation going.

16. Use more open-ended questions

Use more open-ended questions

Image: IStock

Give your conversation partner a chance to answer open-ended questions rather than answering straight yes or no. This is one way to show curiosity, for example, ask open-ended questions such as “What happened today at work that excited you?”

17. Get curious when needed

Displaying genuine curiosity in your partner’s conversation would interest them. Building curiosity can make the conversation more interesting. You may go with “I’m curious to know about…” and make the chat intriguing.

18. Find common ground

The most common way to start bonding with someone new is to find common grounds. For instance, if you both love traveling, you can share each other’s bucket lists. And if you are animal lovers, you may talk about their uniqueness or pets. You may also share stories, ask for advice, or revisit previous topics to make your conversations more engaging.

19. Know the right time to talk

Always is not the best time to have a conversation. Ask them if it is a good time to talk. Sometimes, it could be a bad day, and they could prefer to be calm.

20. Listen intently

Pay attention to what they tell you

Image: IStock

Express to the other person that you are engaged and interested in talking to them. This can make them feel good and try to listen to them actively, which can help strengthen the relationship. The rule of thumb for being a better listener is to not worry too much about what to say next. Pay attention to what the other person is saying. This can keep the text conversation going. People usually open up when they have been heard, seen, noticed, and listened to, even small details of who they are and how they express themselves is important.

Frequently Asked Questions

1. How can I prevent a conversation from becoming dry over text?

You can keep the conversation engaging and flowing by using humor to lighten the mood, selecting topics that appeal to both of you and sharing personal experiences and stories. If the conversation starts to dry out, taking a break and returning to it later can give you time to come up with new things to discuss.

2. How can I encourage a boring texter to talk?

Some people may take longer to warm up or may not be as talkative as others. Asking intriguing questions that show genuine interest can encourage the other person to open up. Sharing an interesting event and asking for their opinion can help spark a conversation and give them something to respond to. It’s important to be empathetic and patient and allow the other person time to respond.

3. How can I use humor effectively to keep a text conversation lively?

People have different preferences regarding humor, so take note of their previous responses or any cues they give about their sense of humor. Puns and clever wordplay can add a touch of wit to your conversation. Look for opportunities to play on words or create a humorous twist based on the context of the conversation. Emojis and GIFs can convey tone and humor effectively in a text conversation.

4. What are some strategies to avoid misunderstandings or miscommunications in text conversations?

Be mindful of your tone and word choice, and ensure your messages are easily understood. Avoid using ambiguous or vague statements that could be interpreted in different ways. Add an extra sentence or two to provide context or clarify your intentions. Emojis and emoticons can help convey tone or emotion in text messages. However, use them sparingly and appropriately, depending on the context and your relationship with the recipient.

5. How can I use personal anecdotes or experiences to make the conversation more relatable?

Personal anecdotes or experiences can be a great way to make conversations more relatable and engaging. Consider the topic or subject being discussed and think about any personal experiences you’ve had that relate to it. Briefly explain the situation, the people involved, and any relevant background information. This helps others understand the context and become more engaged in your story. While personal anecdotes can be captivating, it’s important to be mindful of the conversation flow. Keep your story concise and focused on the key points you want to convey.

6. What are the effective ways to show empathy and support through text messages?

Showing empathy and support through text messages can be a powerful way to connect with someone and provide comfort. Show that you are engaged in the conversation by listening to the other person’s feelings and experiences. Provide encouragement and reassurance to let the person know that you believe in them and that things will improve.

7. How do I handle disagreements or differing opinions while respecting the conversation?

Handling disagreements or differing opinions while maintaining a respectful conversation involves several key principles. Practice active listening by giving attention to the other person’s perspective. Avoid interrupting or formulating a response while speaking, and use respectful and constructive language during the conversation. Avoid personal attacks, derogatory remarks, or dismissive language. If you disagree with a particular point, ask the other person to provide further clarification or expand on their perspective. This approach encourages a deeper understanding of their viewpoint.

Maintaining the other person’s interest and keeping the conversation going can be tricky. However, following a unique texting style and keeping the conversation two-sided can break the monotony and let the other person participate equally. So use more brainstorm ideas for engaging conversations, ask them open-ended questions, and pay attention to details to ensure no miscommunication. Be patient and avoid multi-texting so that you may not look anxious to get a response. Remember, the key to continuing chatting over the text is finding common ground so you both can take turns to express yourselves.

Infographic: Themes For Your Conversation

While you are enlisting the tips that will help keep the conversation going, you also need to remember that not all things are suitable to be discussed over texts. So, what things should you discuss with your partner or friends over texts that will help you kill time better? We have prepared the following infographic to help you with the same. So, read on and remember to make a note of it too!

conversation themes that best work with text messages (infographic)

Illustration: Momjunction Design Team

Get high-quality PDF version by clicking below.

Download Infographic in PDF version Download Infographic
Download Infographic in PDF version

Key Pointers

  • With the advent of technologies, communication has largely become virtual.
  • To master the trick of texting, learning the art of carrying on a conversation is essential.
  • Stand apart by sticking to your own style of texting.

Master the art of sustaining engaging conversations! Discover tips and tricks to keep the conversation flowing and make it enjoyable for everyone!


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  1. Text messaging: Are dependency and Excessive Use discretely different for Japanese university students?;
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