Texting is great for staying in touch when you can't meet someone in person, but getting the conversation going can often be difficult. If you're not ready to say goodbye, but you feel like the conversation has stalled, you may be able to jump-start things by changing the subject or picking up on something you've been talking about. Not sure where to start? Do not worry! This article compiles a list of the different things you can send via text message to make the conversation interesting and fun.
Steps
Method 1 of 13: "What have you been up to lately?"

Step 1. Go old-fashioned with this tried-and-true classic
It may sound basic, but people don't always have much of a chance to talk about themselves. Let the other know that you really care about what is going on in their life and hopefully they will feel comfortable opening up. You may find that they have been working on an interesting project or they may tell you that they have had problems. No matter what they say, build the conversation from there with follow-up questions. If it leads nowhere, talk about something else.
Remember to ask open-ended questions so the person can expand rather than questions that can be answered with "yes" or "no." For example, it is better to ask "What did you do today?" instead of "Did you have a good day?"
Method 2 of 13: "Tell me more about …"

Step 1. Follow up with something they said earlier
A great way to relive a conversation is to pick up on something the other mentioned. You already know that he is interested in talking about it, so ask him for more details. This will show that you are a good listener and by being interested in the person you are talking to will automatically make you seem more interesting.
- You can ask something like "What did you finally choose to eat? Was it tasty?"
- You can also say "I wanted to ask you … Did you say something about planning a trip next weekend. Where are you going?"
Method 3 of 13: "What have you been looking at these days?"

Step 1. Relive the conversation while you get recommendations
If you don't know what else to talk about, find out what the other person reads, watches, or listens to. If you've never heard what he mentions, ask him to tell you a little more.
This is very useful if you mention that you have spent a lot of time at home watching television, reading books or listening to podcasts. Just say something like "I've wanted to get into the podcast world. Where should I start?" or "I need a new marathon program. Do you have any suggestions?"
Method 4 of 13: "What do you think of…?"

Step 1. Get the conversation going by asking for the person's opinion
People are generally happy to share their opinions on things. Use it to your advantage by asking a question that gives the other person a chance to tell you what they really think. Just avoid anything that is too serious. Political and religious debates can get very heated, and it's easy to misinterpret the tone by text message. For added security, opt for a lighter theme.
You can say something like, "Well, I need a serious opinion. Be honest. Waffles, pancakes, or French toast? There is only one correct answer."
Method 5 of 13: "Today, I discovered that …"

Step 1. Take the initiative by talking a little about yourself
Don't feel like you have to constantly pressure the other person to talk about themselves. If you overdo it, she might feel like you're questioning her. If you need a twist, talk about something interesting you've done recently. Hopefully, your interlocutor will pick up the thread and ask you some follow-up questions.
- For example, you can talk about something interesting you learned in school, tell a funny story, or mention that it is the third day in a row that you have seen a rainbow.
- If you haven't done much, talk about something that happens in your life. For example, maybe your little sister dyed your dog purple or you have new neighbors.
- You never know what might start a conversation, so don't be afraid to bring up something random.
Method 6 of 13: "You have the most amazing …"

Step 1. Impress someone with a compliment
You can never go wrong if you say something nice to the person you are talking to. If the conversation stalls, say something you've always liked about her. Even a casual compliment will encourage her to open up a little more with you.
- For example, you can share something you really value about her by saying something like, "You always make me feel good when I'm down. You're the best!" or "I miss your amazing smile."
- You can also mention something that you have that you really like, like "I wanted to ask you where you bought that amazing jacket you were wearing today. It looks great on you!"
Method 7 of 13: "You won't believe …"

Step 1. Engage the person with a moment of maximum suspense
Sometimes it takes a bit of encouragement for someone to really be interested in a conversation. Increase her interest by making her wonder what you will say next. Just make sure the following are important so she doesn't get disappointed.
- If you have a good story to share, start by saying something like "Something crazy happened to me at work today" or "You can't believe who I saw!"
- This can also be a fun way to let the other know that you think of him. For example, if you eat at a restaurant that you know he loves, you can say "Guess where I am right now." (You will earn additional points if you offer to bring him food.)
Method 8 of 13: "During your childhood, did you …?"

Step 1. Learn more about the person by asking about their childhood
If you write to someone you don't know very well but are comfortable with each other, ask questions to find out what they were like during their childhood. This can say a lot about the person, from what their family is like to what is important to them right now. Just keep in mind that childhood memories can be tied to strong emotions, so don't snoop if something seems too sensitive.
Ask lighthearted questions like "Who was your favorite Disney princess as a child?" or "Did you have any awesome holiday traditions as a kid?"
Method 9 of 13: "Do you remember that time …?"

Step 1. Bring up an inside joke or funny story
Make the other person smile by mentioning a funny memory they shared. It could be a distant inside joke between you and your best friend, or something silly the waiter said during your date the weekend before. Just make sure it's something that you both find fun. The other person may be upset if you laugh at something they find embarrassing.
If you can't think of anything, share a funny meme with the person
Method 10 of 13: "I was thinking that …"

Step 1. Mention random thoughts that arise in your mind
Don't worry if it's cool or smart. Go ahead and let it go. If you don't censor yourself, you might be able to think of very interesting things. As a bonus, you can find out if the other person vibrates with your personal brand of weirdness.
For example, you can say "I was wondering why people never evolved with purple hair" or "Have you ever noticed that our math class always smells like mustard?"
Method 11 of 13: "Are you free to make a video call?"

Step 1. Change things up by calling the person
If you feel like texting isn't giving you everything you want, see if the other person is willing to talk on the phone or have a video chat. This way, you'll be able to pick up on more nuances, and it's a great option if you want to talk about something in greater depth than text messages provide.
If the other person says they can't speak because they are busy, you will better understand why the conversation has started to slow down
Method 12 of 13: Nothing

Step 1. Wait a while before sending a message again
Sometimes when a conversation slows down, it's because the other person is busy or bored texting. Maybe you have something else in mind. Instead of filling each moment of silence, give him some space to decide if he wants to take the lead in the conversation or take a break for a bit.
You don't need to completely ignore the person, and don't make it a waiting game where you don't respond for exactly 17 and a half minutes. Just find something else to do for a while and see if she feels like talking
Method 13 of 13: "Let's talk later!"

Step 1. Let the conversation end if you feel there is no more to talk about
If the person you're writing to sends short replies or takes a long time between messages, they may be ready to take a break. Instead of leaving things open, give them a clear ending with a friendly "Bye." This will also make it easier for you to come back with a new conversation a day or two later.