22 Tips to Keep a Conversation Going Over Text
Add warmth and personality to messages for more engaging, meaningful interactions.
Texting has become one of the most popular forms of communication in our daily lives, transforming the way we build and maintain relationships. While initiating a conversation over text is relatively easy, keeping it going and making it interesting requires skill and consideration. Whether you are reaching out to a friend, partner, or new acquaintance, these 22 proven tips will help you sustain engaging, enjoyable, and meaningful conversations over text.
1. Keep the Conversation Two-Sided
Effective texting is a two-way exchange. Avoid dominating the conversation with only your thoughts or topics. Instead, ask about your texting partner’s interests and experiences. Notice what excites them and tailor your questions accordingly.
- For example: If they love the show Friends, ask, “What’s your favorite episode of Friends and why?”
- Wait for their response before moving to the next message; don’t overwhelm them with multiple texts in a row.
2. Develop Your Unique Texting Style
Everyone appreciates individuality. Let your personality shine through your texts, whether it’s humor, wit, or a supportive tone. Emojis can add flavor, but use them sparingly and contextually.
- Text simple greetings: “Good morning! Hope you have an amazing day!”
- Add humor when appropriate to keep things lighthearted.
3. Make Them Feel Special
Show that you value your conversation partner. Compliment their achievements, remember little details they’ve shared, and express appreciation.
- Example: “How did your interview go today? I was thinking about you.”
4. Pay Attention to Details
Carefully read their messages and respond to specifics. Proofread your messages to avoid misunderstandings caused by typos or unclear grammar. Following up on previous discussions shows you listened.
- “You mentioned your dog was sick last week — how’s he feeling now?”
5. Stay Relaxed
Don’t stress about crafting a perfect reply. Take your time, type at your own pace, and let the conversation flow naturally. Avoid trying too hard to impress or acting out of character.
6. Be Yourself
Authenticity is attractive. If you’re naturally witty or sarcastic, don’t hide it (as long as it’s context-appropriate). Avoid overusing abbreviations to prevent confusion.
- Instead of “brb,” try “I’ll be back in a few minutes.”
7. Know When to Close the Chat
If you need to end the conversation, do so gracefully to prevent confusion or hurt feelings. Transparency sets expectations and can keep prospects for future conversations alive.
- “I have to head out for a bit, but I’d love to pick this up later!”
8. Use Past Conversations
Referencing topics from earlier chats shows that you remember and care. This approach can also revive a flagging conversation or serve as a natural reentry point.
- “Last week you said you were starting a new book — how’s it going?”
9. Keep Things Light
People gravitate toward positivity and happiness. Keep your texts fun, talk about uplifting experiences, or share light jokes to foster a warm atmosphere.
- Share experiences from your day.
- Swapping funny memes or stories can make the exchange enjoyable.
10. Avoid Multi-Texting
Sending a flurry of messages can appear overwhelming or needy. Let the conversation breathe — patience keeps things comfortable for both parties.
- If you receive too many texts at once, respond directly and openly rather than making assumptions.
11. Be Patient
Not everyone can reply instantly. Understand that your texting partner has their own schedule and commitments. Give them space, and don’t jump to conclusions if they take a while to respond.
- Check in periodically, but avoid excessive follow-ups.
12. Use Memes for Connection
Memes can be a bonding shortcut — especially when they’re funny or relatable. They quickly inject humor and can revive slow conversations.
- Make sure the meme suits your partner’s sense of humor.
- Wait for their reaction before following up.
13. Surprise Them with a Call
Sometimes, switching from text to a call can deepen your connection or clarify a discussion that’s going nowhere over text. A surprise (well-timed) call often makes the other person feel valued.
- Ask if it’s okay to call or simply say, “Would you like to chat for a few minutes?”
14. Ask Open-Ended Questions
Open-ended questions invite detailed responses, making conversations more engaging. They require thought and encourage longer replies compared to simple yes/no questions.
- “What was the highlight of your week?”
- “If you could travel anywhere, where would you go and why?”
15. Share Stories and Personal Experiences
Stories create connection and give your texting partner something to relate to or ask about. Share what made you laugh today or an interesting thing you noticed.
- Be genuine, and keep details relevant and brief.
16. Be Attentive to Their Mood
Not every day is the same for everyone. If you sense a change in their texting style (short answers, lack of emojis), check in supportively rather than pressing for engagement.
- “You seem a bit quiet today — everything okay?”
17. Use Compliments Thoughtfully
A genuine compliment can make someone’s day and encourages them to keep chatting. Remember to be specific and sincere — generic flattery rarely makes an impact.
- “You always know how to pick the perfect movie!”
18. Respond Promptly When Possible
Timely replies demonstrate interest, especially in the early stages of building rapport. However, balance promptness with your own availability and comfort.
- If you can’t reply right away, let them know (“I’ll get back to you in a bit — on a call right now!”).
19. Don’t Overthink Every Message
It’s easy to fall into the trap of analyzing every word or emoji. Simple, honest messages often feel more authentic and less forced.
- Trust your instincts and refrain from editing or rewriting excessively.
20. Mix Up Conversation Topics
Variety keeps conversations fresh. Alternate between fun, meaningful, and even silly subjects to maintain engagement.
- “What’s a weird fact about you that most people don’t know?”
21. Share Photos or Interesting Content
Photos, GIFs, and articles can add a new dimension to your conversation. They provide visual cues and new talking points.
- Share a picture of your pet or something funny you saw — just make sure it’s appropriate and welcome.
22. Know When to Take the Conversation Offline
Certain topics or moments may be better suited for a phone or video call, or an in-person conversation. If texting feels limiting, suggest moving the chat to another medium.
- “Would you like to grab coffee this weekend and chat in person?”
Texting Etiquette: Do’s and Don’ts
In addition to using the above strategies, it’s important to observe good texting etiquette to avoid common pitfalls.
- Don’t use text as your main conflict resolution tool. Serious issues are often best discussed in person or via a call.
- Don’t send ambiguous emoji or tone-heavy messages that might be misinterpreted.
- Do check your recipient’s texting preferences — some people enjoy frequent messaging, while others prefer periodic check-ins.
- Do know when to step away and give your partner time to respond.
Examples of Keeping a Conversation Alive Over Text
| Do | Don’t |
|---|---|
| “What was the best part of your day?” | “Hey” or “What’s up?” (without follow-up) |
| Share a funny meme that made you laugh | Send repeated “hello?” or multiple unanswered messages |
| Reference something from a past conversation | Only talk about yourself |
| Say, “Let me know when you’re free to talk more!” if ending chat | Disappear without a word |
Frequently Asked Questions (FAQs)
Q: How do I keep a conversation going with someone who gives short answers?
A: Try asking more open-ended questions or bringing up topics you know they enjoy. Sometimes, people respond briefly because they’re busy, distracted, or shy. Give them space, adjust your expectations, and remember that engaging conversation is a two-way street.
Q: What should I do if the conversation goes dry?
A: If things stall, switch topics, share a meme or funny story, or ask for their opinion on something you know they care about. Alternatively, take a break and reconnect later — sometimes space is what’s needed to reignite interest.
Q: Is it okay to send memes or GIFs to keep the conversation lively?
A: Absolutely! Memes, GIFs, and photos add levity and visual interest, making conversations more dynamic. Just make sure the content aligns with your partner’s humor and preferences.
Q: How can I tell if someone is not interested in texting me?
A: Consistently short replies, lack of questions, delayed responses, and no effort to keep the conversation going may signal disinterest. It’s best to step back and respect their space.
Q: When should I switch from texting to calling or meeting in person?
A: If the topic is sensitive, nuanced, or if you feel more connected through voice, suggest a call or video chat. Similarly, if the connection grows, meeting in person can foster a stronger bond than texting alone.
Final Thoughts
Keeping a conversation going over text is both an art and a skill. By applying these strategies — from asking thoughtful questions to sharing a laugh — you build trust, deepen connections, and ensure enjoyable, memorable exchanges. Remember to be patient, authentic, and attentive to both verbal and nonverbal cues for lasting, rewarding relationships in the digital age.
References
- https://www.momjunction.com/articles/how-to-keep-a-conversation-going-over-text_00775410/
- https://www.joinonelove.org/learn/texting-dos-and-donts-in-relationships/
- https://www.youtube.com/watch?v=pcB28nLP3LE
- https://www.momjunction.com/articles/how-top-keep-the-conversation-going-with-a-girl_00760908/
- https://www.scribd.com/document/805145639/251-Bold-Flirty-and-Thoughtful-Questions-to-Ask-Your-Crush-MomJunction
- https://matthewhussey.com/blog/17-texting-tips-that-lead-to-commitment/
- https://helloprenup.com/communication/75-conversation-starters-over-text/
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