17 Ways to Keep a Text Conversation Going

Published April 20, 2020
Man sitting on sofa using cell phone

Explore easy, creative ways to keep a romantic text conversation going. The last thing you want is for your text conversation to dry up before it even gets started. Asking the right questions at the right time ensures your romantic texting continues.

1. Ask Open-Ended Questions

It's always best to ask a question that is open-ended. This type of question can't be answered with a yes or no or other one-word replies. For example:

  • Closed question: "How are you today?" Usually receives a one-word response making for an awkward end to the conversation.
  • Open-ended question: "What kind of things did you have going on today?" You can then ask more open-ended questions based on the response.
  • Open-ended question: What happened today at work/school that you found exciting or interesting?

2. Make Your Questions Flirty

How do you keep a girl interested when texting? A few tips can help you have a meaningful and ongoing conversation with a girl over text messaging. Instead of simply asking what she was doing today, phrase your question so your personality shines through. While you're getting to know her, she's getting to know you. If you have a fun and flirty personality, then let her see it. For example, you could ask her:

  • "What kind of rules did you break today?"
  • "What kind of mischief did you cause today?"
  • "What naughty thing did you do today?"

3. Getting to Know You Ice Breakers

When texting someone new, questions or lead-in requests are a great way to get to know her. What do you want to know about her? Think in terms of meeting someone in-person and how that conversation might go. For example, you could text:

  • "Tell me about your job [fundraiser, school, etc]. What do you like about it?"
  • "What do you like about living in [insert town/city]?"
  • "Why did you decide to go into [career or college major]?'
woman with smart phone

4. Participate in the Conversation

You want your texting to be an actual conversation, not a 20-question drill or a speed-dating quiz. The questions should be used as a way to lead and continue the conversation. That means it should be a two-way exchange. For example, you should contribute something to each response that shares a little about yourself in a natural conversational manner.

  • Her: "I became interested in healthcare when I was in high school."
  • You: "Ah... Very studious. My interests were less ambitious - the next football game." (smiley face)
  • Her: "You played?"
  • You: "Yeah, quarterback. So, what happened in HS that made you interested in HC?"

5. How to Keep a Text Conversation Going

Once you get the conversation rolling by sharing a little about yourself, continue to redirect it back to her. If the conversation about her interest in something dries up, quickly shift to another subject that is related. Don't just jump into a completely different topic. The key is to allow your conversation to progress similar to an in-person conversation would.

  • Ask her what college she went to or what college she plans to attend.
  • Listen to her response and continue to inquire about her career or college plans.
  • If she has graduated and enjoys a career, ask her about her workplace.
  • If she hasn't started college and it's long-distance, ask if she's familiar with the city.
  • If you have been to the city, then you can add some details about what you know. She'll probably have questions for you.

6. How to Text Asking for a Date

Once you've established a rapport and you want to take your conversation to the next level, you should arrange to meet up in-person for your first date (or date early in your relationship). The most acceptable way is to text for a coffee date. Set a date and time and then show up prepared to have an in-person conversation.

7. Plan Ahead to Keep a Text Conversation Going

Whether you're texting with a romantic partner or a potential one, you should have a good idea about how you wish your conversation to go. Prepare a few topics ahead of time to help you keep the conversation on track. Don't type out your questions as though rehearsed. Allow the conversation to have a natural flow. Choose topics that are relative to the person, your region, company they work for, career, and other personal interests.

Thoughtful man relaxing at home

8. Use the Weather As Lead-in to Broader Text Conversation

Talking about the weather doesn't have to be mundane. It's a great lead-in to a texting conversation. There are a few things you can do to ensure your conversation doesn't die an awkward and painful death. The weather is a great way to start a text conversation and can lead to many other weather-related topics. The weather offers a segue to discover more about what the person is doing or may be planning to do.

  • "Did you get a lot of snow last night?"
  • "We had a bad thunderstorm last night. How was it where you are?"
  • "Wow, it got cold really fast. How is it where you are?"

9. Talk About Holidays As a Texting Ice Breaker

There are many holidays year-round. Depending on the time of year, you can text about a past or upcoming holiday to break the ice for your first text message with a new romantic interest.

  • "What do you like most about [insert a holiday]?"
  • "It was really hot this fourth of July. How did you celebrate?"
  • "Where do you go for Thanksgiving?"
  • "Where are you going to be July 4?"

If your romantic interest doesn't have plans for the upcoming holiday, make some together.

10. Generic Types of Questions for Text Conversations

There are some generic questions you can use or frame to fit your personal situation. You can always embellish them to reflect your personality. Each question can lead to a much larger and fuller conversation.

  • "What makes you happy?"
  • "What's your favorite food?"
  • "What is your favorite movie?"

11. How to Resuscitate a Dying Text Conversation

Keeping a conversation going with anyone requires a little texting knowhow. If your relationship is new, you can use that list of possible topics to have in mind should your conversation die out. If your conversation stalls, you can change the subject by texting something like:

  • "Oh, I just remembered…"
  • "I just got a notification about a new TV series…"
  • "My friend, George, just texted me about [insert topic]. What do you think about it?"

12. How to Steer a Text Conversation in New Direction

If your text conversation seems to be going nowhere and is rapidly growing mundane and boring, you can always take it in a new direction. One ideal way to do this is to text, "Not to change the subject, but I just [saw the trailer for a new movie, a flyer for a new art exhibit, etc]…" Then ask her/his opinion and if she/he likes that type of movie or art. If she/he does, then you have a perfect segue for a date.

woman with cell phone

13. One Topic Reminds You of Another Topic

If at any point your conversation stalls, be prepared to jump to another topic. You can seamlessly move to a different topic by saying, "That reminds me of something I [saw, read or heard]…" and then continue discussing the new topic.

14. Revive a Stalled Text Conversation With Music

Another question that can revive a stalled text conversation is to ask her/his opinion about a song or bad. You could text, "I just heard this really cool song [give details or text a link]. What do you think of it?" This will lead to a conversation about music and all kinds of related topics. You'll quickly discover if the two of you have the same taste in music.

15. Tell a Joke to Keep a Text Conversation Going

If you're having trouble keeping your text conversation moving along, try a joke. If you don't know the other person very well, keep the joke clean and generic. Just make sure it's funny! An easy segue might be, "Hey, don't mean to veer us in a different direction, but my buddy just sent me a joke you might appreciate…" then text the joke and go from there.

16. Play a Text Game to Keep Engaged in a Text Conversation

One way to keep your romantic partner engaged in your text conversation is to play a text game. You can find several question games online, such as Would You Rather or Never Have I. For more fun, take turns asking the questions, so each of you has a chance to discover more about the other.

17. Topics to Avoid to Keep Your Text Conversation Going

There are two topics that most social mores dictate should not be discussed since people have very strong opinions about them- religion and politics. The quickest way to put an end to a text conversation with someone new before it gets going is to text about religion and/or politics. The only exception is if you already know the other person's affiliations and they hopefully mirror your own.

17 Ways You Can Keep a Romantic Text Conversation Going

These 17 ways to help you keep your romantic text conversation from stalling are easy to use. Each tactic provides you with a small arsenal of ideas to ensure you have quality text conversations with your romantic partner.

17 Ways to Keep a Text Conversation Going