How to Start a Conversation Over Text (+ Common Mistakes)

Scientifically reviewed by Viktor Sander B.Sc., B.A.

These days, almost everyone keeps in touch via text or instant messaging, and many of us message new friends or partners first before talking on the phone or face to face. But it’s not always easy to initiate a conversation. You might feel awkward about reaching out or unsure what to say in your opening message.

In this guide, you’ll learn how to begin a fun conversation over text with someone you already know or someone you just met online, for example, on a dating app such as Tinder, a social media platform such as Facebook, or an online community.

Sections

  1. How to start a conversation over text
  2. How to start a conversation over text after a fight
  3. Common mistakes when starting a text conversation
  4. Signs to move on and stop texting

How to start a conversation over text

If you are struggling to think of things to talk about or aren’t sure what kind of opening lines work best, here are some examples of ways you can begin a text conversation.

1. Re-introduce yourself

When you’re texting someone you recently met in person for the first time, use your first text to re-introduce yourself. If they gave you their number, but they don’t have yours, they might not realize who is messaging them. To save confusion, remind them of your name and how you met.

For example, here are some ways you could re-introduce yourself:

  • Hey, it’s [Your name] from dog training class!
  • Hi, it’s [Your name] from the crochet workshop.
  • Hi there! This is [Your name] from the coffee shop 🙂
  • Hey, it’s [Your name] from the party. Rick gave me your number 🙂

2. Continue a previous conversation

If you have already spoken to someone, whether in person or online, it can be easier to continue a previous conversation rather than thinking of a new topic.

Here are some opening texts that could continue a face-to-face or online conversation:

  • Hey! Did you ever get around to trying that new chili recipe you were telling me about?
  • Hi! 🙂 I think you told me you were going to a conference yesterday. How was it?
  • So I’ve thought more about our book conversation, and I can’t believe I forgot to mention how much I love We Need To Talk About Kevin. Have you read it?

3. Mention something from a profile or post

If you are talking to a stranger online, look at their profile, bio, or something they recently posted. You may be able to find a few good conversation starters. Open with a simple statement or compliment, followed by a question.

Here are some examples of opening messages you could send to someone online:

  • [On a craft forum]: I loved your recent post on how to upcycle coffee tables. Do you have any photos of your work online?
  • [On a dating app]: It looks like you love to hike. Where was the second photo in your profile taken?
  • [On an Instagram post]: That is such a stunning terrarium. I’ve never seen stones that color. Where did you get them?

If you want to talk to a stranger, try to build rapport and trust by leaving public messages or comments before messaging them directly.

4. Ask them for expert advice

If you are messaging someone who has a particular passion or interest, tap into their expertise. You may start a conversation about something they love, and they might be flattered that you’ve asked for their advice.

For example, if you know that the person you’re talking to loves dogs, you could send them a photo of an unusual-looking dog you saw in the park and say, “Hey, I know you’re a bit of a dog expert. What breed is this? It’s so cute.”

In this case, you could then move the conversation to the pros and cons of various dog breeds, dogs the other person has owned in the past, and other dog-related topics.

Alternatively, you could show someone that you value their opinion by asking them to help you make a decision. Let’s say they’re keen on fashion and you’re shopping for shoes online. You could send them links and say, “So I’m in need of your advice! I’ve got these shoes in my basket. What do you think would work best with dark jeans: the blue pair or the ones with red stripes?”

5. Ask for their opinion of a celebrity’s post

If you’re talking to someone who follows celebrity culture, mentioning something a famous person has posted online could be a good conversation starter. For example, you could say, “Wow, just saw [Name’s] latest Tweet…I wasn’t expecting that! Have you read it?!”

6. Send a text that piques their interest

Instead of making a statement about something that has happened to you, add some interest and drama by sending a “teaser” text that piques their interest. You can then reveal the rest of the story once they’ve replied.

Here are some examples of texts that could make them curious:

  • You won’t believe what happened to me this morning!
  • Guess what I saw on my way to the store? I’ll give you three tries.
  • You’ll never guess what came through the mail today.

7. Send a GIF, meme, or emoji

Get into the habit of saving funny or thought-provoking memes, GIFs, videos, and articles you find online. They can be effective conversation starters, especially if they are related to the other person’s hobbies or interests.

For example, if you’re talking to someone who loves nature, you could send them a video clip of an unusual or newly-discovered species and ask, “Have you seen this before?”

8. Say “thank you” for a recommendation

If someone has recommended something and you enjoyed it, open a text conversation by thanking them. Be specific; tell them exactly why you liked it. Add a follow-up question too, and you might be more likely to get a response.

Here are some ways you can thank someone for a recommendation and start a conversation at the same time:

  • I just finished watching [name of TV show]. I loved it. Thanks for the recommendation! Got to admit that the ending took me completely by surprise! Did you see it coming?
  • I finished reading [name of a book they recommended], and I’m so happy you recommended it to me. I love the way the narrator speaks. It’s hilarious. Would you recommend the others in the series?

9. Talk about current or upcoming holidays

Holidays can be a great conversation topic. You could ask someone how they’re planning to celebrate a holiday, what they like or dislike about it, or if the holiday has recently passed, whether they had a good time.

For example, you could say, “Can’t believe it’s March already! What are you doing for Spring Break?” or “December 1st: Christmas has officially started! Have you heard any cheesy Xmas songs yet?”

10. Open with a flirtatious message

The tips in this guide don’t apply only to friends; they are also useful if you’re texting a guy or a girl you like. You don’t need to use any special lines or tricks when you talk to your crush.

But to make your feelings clear, you could try opening a conversation with a light-hearted, flirtatious message when you’re texting someone you like.

Here are some examples of how you can open a text conversation by flirting:

  • I’m in a coffee shop, and I was just curious: what type of coffee do you drink on a first date?
  • I forgot to tell you earlier that your haircut makes you look even cuter than usual 😉
  • I’ve got a pint of ice cream and two spoons. It’s a shame you’re not here…

Follow the other person’s lead when flirting. If they don’t reciprocate, pull back. They might feel more comfortable flirting with you later when you know each other better.

11. Let the other person know it was good to see them

If you’ve recently hung out with someone, start a conversation by saying something positive about your time together. This kind of message will probably make them feel flattered, and it’s a natural way of making it clear that you’d like to see them again.

For example, here are some ways you could let them know how much you enjoyed hanging out with them:

  • [To someone you went on a date with]: I had a great time last night! I can’t remember the last time I laughed so much. I’d really like to meet up again.
  • [To someone you hung out with online]: That was the best Zoom call I’ve ever had. We should definitely watch more films together.

12. Give them a compliment

A sincere compliment can be a positive way to open a conversation. Most people appreciate it when someone else notices their talents or interests. Encourage the other person to open up by adding a question.

For example, here are some compliments you could use to start a conversation over text:

  • [To someone on a dating site]: I love that photo where you’re abseiling. It looks like you’re having an awesome time! Do you do any other outdoor sports?
  • [To someone you met in art class]: The charcoal sketch you made in class yesterday was just amazing! Do you ever use charcoal and pastels together?

Depending on the situation, you could compliment someone’s appearance. For example, if you’re flirting with someone on a dating site, it’s generally OK to let someone know that you think they’re attractive.

However, generic compliments (e.g., “You’re so pretty”) are usually best avoided. They can come across as shallow and low-effort. Instead, try learning more about the other person and compliment their traits, skills, or achievements instead. If you want to compliment their appearance, highlight something specific (e.g., “Your eyes are amazing, they’re such an unusual color”).

Check out our guide on how to give compliments for more tips.

13. Send a photo or short video clip of your pet

A photo or short clip of your pet can be a fun way of opening a conversation. For example, you could caption a photo of your dog sitting next to a chewed cushion with “Look what he did this morning!” or “He’s lucky that I love him so much!”

14. Ask an offbeat or funny question

If you know that the person you’re texting has an offbeat sense of humor, you could send them a slightly random or thought-provoking question.

If you’re anxious that your text will seem too random, briefly explain why you’re thinking about the topic in the first place. For instance, if you’re stuck waiting for a train, you might have time to think about philosophical questions.

Here are a few examples of how you can use a quirky question to start a conversation:

  • I’m stuck waiting for my bus, so naturally, I’ve started to think about robots. So, do you think people will start having romantic relationships with robots in our lifetime?
  • OK, I’ve got an important question for you: Would you rather be reincarnated as a skunk or a dolphin? And yes, I am bored at work.

For more ideas, check out our list of fun questions for any situation and deep questions to truly get to know someone.

15. Acknowledge long periods of silence

When you’re texting someone you haven’t been in contact with for some time, begin by explaining your silence and acknowledging that it’s been a while since you were last in touch.

End your text with a question, preferably about something that’s going on in their life.

You may be able to get some inspiration from their social media posts, or you could try reaching out on a special occasion, such as a birthday or holiday.

Here are a couple of texts you could send to someone after radio silence:

  • I apologize for not staying in touch. I’ve been so busy with law school, and the year has just flown past. I saw on Facebook that you’ve just started a business. How exciting! What kind of stuff are you selling?
  • So sorry for the silence. Work has been nonstop lately. Hope you’re having a lovely Christmas. Are you doing anything special?

If you want to reconnect with a friend over text after months or years apart, check out our article on how to text someone you haven’t talked to in a long time.

How to start a conversation over text after a fight

Opening a text conversation with a thoughtful apology after a fight can be the first step to reconciliation.

In most situations, you should try to:

  • Acknowledge exactly what you did
  • Acknowledge that you have hurt the other person’s feelings
  • Offer to make amends or ask if there’s any way you can make it up to the other person
  • Give the other person space to process what you have said

Do not demand forgiveness. It is up to the other person whether or not they can move past what has happened. You may need to follow up with an in-person meeting or phone call, depending on the situation and what the other person wants.

Here’s an example of an apology that could work well over text:

“I deeply regret criticizing the decorations you chose for your wedding. It was a thoughtless and unnecessary thing to say, and I am very sorry for upsetting you at what should be a really happy time. If there’s anything I can do to make it up to you, please let me know. If and when you’re ready to talk, I’d love to hear from you.”

For in-depth advice on how to text a friend after a fight, read more about sending sorry messages to a friend.

Common mistakes when starting a text conversation

If your text conversations dry up quickly or you hardly ever get replies, you might be making some of the following mistakes:

1. Using the wrong tone

One of the drawbacks of texting is that your recipient might misunderstand the tone of your messages. For example, you might think it’s obvious that you’re joking or using sarcasm, but because humor is subjective, it might not translate over text.

If you aren’t sure whether you’re using the right tone, it can help to read a message out loud before you send it. You could also ask yourself, “Could this be interpreted in more than one way?” If there’s a reasonable chance your message could be misunderstood, rewrite it.

2. Using incorrect spelling and grammar

Lots of people are annoyed by incorrect spelling and grammar. You don’t need to be a great writer, but it’s a good idea to use autocorrect and proofread your messages before you send them. Text speak usually comes across as irritating, so as a general rule, it’s better to type out full words and sentences.

3. Sending texts at the wrong time of day

It’s usually best to avoid sending a text late at night. It’s likely that your recipient will want to go to bed rather than reply to your messages. Late-night messaging can also come across as inappropriate if you’re still in the early stages of getting to know someone.

4. Apologizing for starting a conversation

Assuming that you are polite and respectful, there is no need to apologize when you reach out to someone. Remember, if someone does not want to talk to you, they can choose to give minimal answers, wait a long time before replying, or simply not respond at all.

For example, do not say “Sorry to bother you, but…” or “I’m sure you get lots of messages, and I hope I’m not being a nuisance…”

5. Starting a conversation when you are busy

You don’t have to reply to a text immediately, but if you send a message and wait a long time before you reply to the other person, you may come across as rude. If you want to send someone a message just to let them know you’re thinking of them and you’re busy, tell them you won’t be able to reply for a while.

6. Diving straight into heavy topics

Most of the time, you don’t know what someone is doing or what kind of mood they’re in when you send them your first text.

If you dive straight into a heavy or complicated topic, such as politics or your relationship problems, your recipient might feel overwhelmed. They may feel obliged to send an equally serious response, which they may not have the time or energy to do. Keep the conversation light at the beginning. You can move on to more intense topics later in the conversation if you both have time for an in-depth discussion.

As with most guidelines, there are exceptions. For example, if you are messaging a friend or partner and you know they are happy to have debates or deep conversations over text, it’s fine to open with a weighty question or statement.

7. Sending very long messages

Messages that are more than two or three sentences long are probably too long for most text conversations. If you are both sending lengthy messages back and forth, suggest that you speak on the phone or exchange voice messages instead.

8. Sending multiple messages in a row

If someone doesn’t reply to your message, resist the temptation to send them another message. It won’t necessarily encourage them to reply, and you may come across as needy. Do not ask someone why they haven’t replied, and never demand a response. No one is obliged to give you an answer, and making demands could make the other person feel pressured or harassed.

9. Asking too many closed questions

Closed questions can be answered with a “Yes” or “No.” Closed questions aren’t always bad, but if you want to start an interesting conversation, it’s better to ask open questions too. An open question encourages the other person to give you a fuller answer, which you can then build on. Open questions often start with “What,” “Where,” “When,” “How,” or “Who.”

Here are some examples of closed questions:

  • “Did you have a nice vacation?”
  • “Did you hear about the job online?”
  • “Do you like your neighbors?”

Here are some examples of open questions:

  • “What was the best part of your vacation?”
  • “How did you hear about the job?”
  • “What do you think of your neighbors?”

Signs to move on and stop texting

Here are a few signs that someone would prefer you to contact them less often or to stop contacting them altogether.

1. They never text you first

If you are always the one to initiate text conversations, it may be a sign that the other person isn’t very interested in getting to know you.

However, bear in mind that some people are shy and feel awkward about reaching out. If you have great conversations over text or in person, and they are clearly interested in meeting up, you may just need to accept that you’ll always be the one to text first.

2. They take a long time to reply

Some people have busy lives. But in general, if someone wants to stay in touch with you, they will make time or at least explain why they can’t text much. If they often say “I’m busy,” it’s usually a sign that messaging you is a low priority.

Others deliberately vary the amount of time they wait before responding to a text because they think it makes them appear mysterious or “hard to get.” They might wait hours or even days before responding. This kind of game playing is usually a red flag. It suggests that someone isn’t willing or able to communicate in a healthy way.

You can learn more here about why some friends don’t text back and what you can do.

3. They only give you short answers

Someone who wants to keep a conversation going will usually give you answers you can build on instead of short replies.

Of course, there are people who just aren’t very good at keeping a conversation going over text, and some who prefer to talk in person. If they are warm and engaging when you meet up or talk on the phone, it may not matter that they aren’t a big texter.

4. They don’t ask you any questions

Some people simply don’t understand that enjoyable conversations involve an exchange of questions and answers. But in most cases, someone who doesn’t ask you any questions about yourself probably isn’t interested in getting to know you.

5. They usually text you late at night

It’s not always a bad sign if someone often texts you late at night. For example, they may work long hours, and late in the evening might be their least busy time of day.

But texting late at night can imply that they don’t respect your need for sleep. Late-night conversations might also turn sexual quickly, which can be uncomfortable if you don’t want to swap those kinds of messages.

6. They send you lots of sexual texts

As a general rule, people who take a conversation in a sexual direction early on are not looking for a meaningful friendship or romantic relationship. So unless you are looking for the same thing, it’s best to stop texting if the other person appears to be mostly or only interested in sex.

7. They message you but aren’t keen to meet up

Unfortunately, some people enjoy messaging and flirting with others online but have no intention of meeting up or starting a relationship. They may use apps because they are bored and want to kill time or just because they like getting attention.

If you’ve asked someone to meet, but they don’t seem keen, or they repeatedly make excuses and cancel plans, it’s probably best to focus on other people.

8. They ask you to stop texting them

If a person tells you that they don’t want to hear from you anymore, respect their boundaries and do not message them again.

Remember that contacting someone who has told you they aren’t interested in talking anymore is harassment. Depending on where you live, sending unwanted messages can be a criminal offense.

David Morin is the founder of SocialSelf. He's been writing about social skills since 2012. Follow on Twitter or read more.

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