30+ Texting Conversation Starters


It’s funny how getting a “hello” for texting conversation starters makes you feel like a pre-teen on AOL instant messaging (more commonly known as AIM). Most of us answer with the same energy we receive, so if someone says “hello,” we’ll say “hey” or “what’s up.” It almost feels odd that the dialogue doesn’t end with “nm u?”

Of course, these types of chats aren’t conducive to getting to know one another or piqueing anyone’s interest, and they’re unlikely to result in a date. If you’re online dating, you might have to rely on your text messaging banter to win someone over, which can be difficult.

Here’s a suggestion and/or challenge: never text “hello.”

“Hey,” “hi,” or “hello” are words I rarely respond to. I take a look at the text and decide to give the person some time to tell me what they’re looking for.

If you’re texting someone on an app (especially a straight, cis woman), chances are they’re getting a lot of messages. You want yours to be different from the others! You still want to engage the person you’re messaging with and make texting fun if you’ve switched to texting.

Here are some texting conversation starters that are just as cool and casual as “hello,” but will actually lead to engaging discussions that will help you and the person you’re texting get to know each other better.

30 Texting Conversation Starters that are Casual, Cool, and Intriguing!

1. What was your favourite aspect of the day?

This is one of my favourite texting conversation starters since it takes the standard “how’s your day?”

2. How’s it going today?

This classic book, on the other hand, is never a terrible idea. It demonstrates that you are interested in their day and sounds more pleasant than “what’s up?”

3. Welcome to the day. What are the plans for today?

Another option to inquire about their day is to do so first thing in the morning. It can also serve as an icebreaker if you want to ask them out that day because you’ll be able to see whether they’re available.

4. How is your week shaping up?

This is a terrific method to transform texting into a date if you’re not a huge texter. Find out when they are available and make some plans!

5. Where should our first date take place?

Another text opening to demonstrate that you’re not trying to waste time with small talk, but this can also lead to a discussion about their hobbies, favourite foods, and so on.

6. What are three emojis that best describe your day thus far? I’ll take the lead…

This SMS is a lovely approach to inquire about someone’s day, especially if neither of you is particularly gifted with words. You can ask questions based on the emojis they give to keep the conversation going.

7. What is your favourite type of food?

This text works best when accompanied by an eye emoji, which allows you to preview the next question you’re about to ask. And the question you’re about to ask is, “I love Thai food as well!” On my block, there’s a fantastic establishment. “Can you tell me when you’ll be free so I can take you there?”

8. I’m hoping this was your reaction when my name appeared on your phone: *insert sweet GIF or emoji here*

This is flirty and sweet, and it’s a wonderful approach to start a conversation without going too deep.

9. Hello and good morning!

Take the good morning text, but add something fresh to your knowledge of the person you’re contacting. After all, in a partnership, synchronised sleep cycles are crucial.

10. Today is such a beautiful day! Do you want to go for a walk or something?

Again, winning texting conversation starters turn a simple small talk topic into a potential date or something more exciting.

11. Thinking of you and wishing you a wonderful day!

If you want to contact someone but aren’t sure if either of you has time right now, this is a fantastic method to stay in touch without taking up too much of their time.

12. Do you have a favourite cocktail? I guess I’m going to need one after the day I’ve had.

This simultaneously asks a question about them and tells them something about yourself. It’ll also make them wonder why your day is so difficult.

13. You were in my dream the night before last.

Texting conversation starters elicit a response, and no one can resist responding with, “What happened in your dream?”

14. What is your astrological sign?

Whatever you think of horoscopes, they may tell you a lot about a person. If your date merely responds with their sign, inquire as to whether or not they believe the description matches their personality.

15. Did you hear about [insert current event here]? What are your thoughts on the matter?

Personally, I don’t think politics is a fun topic to flirt with, so stick to celebrity news, viral internet sensations, or something less divisive.

16. Are you having any fun at work today?

At this point, you presumably know what they do for a living, but do you really? If they enjoy what they do, they’ll most likely enjoy telling you about it, which will earn you brownie points!

17. I saw your Instagram photo and those donuts look incredible! How did they fare?

If you follow each other on social media, you may easily piggyback on their postings for natural discussion starters.

18. I just came upon your Instagram post…

I believe we will need to return to the doughnut shop, and this time I will purchase a donut.

You may also use their social media posts to ask them out on a date if you’re a little more brave!

19. What was the outcome of your [interview/meeting/test]?

This may sound insignificant, but you’d be amazed how much it means to someone when you realise they have a big event that day.

20. Could you assist me in deciding between [X] and [Y]?

Did you realise that requesting favours makes others like you more? Furthermore, asking for someone’s input makes them feel special. Inquire about which tie to wear tomorrow (with photos), which rug to order for your new apartment, or which ice cream flavour to pick up at the supermarket. Perhaps they’ll even invite themselves over for ice cream with you!

21. Hello there! What are your plans for the week? Let’s get together for supper one night?

Simple, straightforward, and to the point. It’s impossible to go wrong here.

22. Have you heard the new album by [band]? So far, this is my favourite music.

If you’ve already talked about music and are on the same page, this content will be more effective. They might not recognise the artist you’re talking about if they’re into EDM and you’re into country.

23. This song makes me think of you *insert song link here*

Always endearing, and who doesn’t enjoy music suggestions?

24. Do you have a guilty pleasure? I’m not ashamed to disclose that I’m currently watching The Bachelor.

When you include a morsel of information about yourself, like this, interesting queries appear to work best and come across more casually.

25. I just thought I’d say hello because you came to mind.

While this isn’t much more than a standard “hello” text, it’s a lot prettier and will almost certainly earn you a better reaction.

26. You’re looking fantastic right now. I can’t see you, but I know you’re there because you always are.

This is a flirty, entertaining text to send that will definitely make your date smile.

27. Email me the most recent meme you downloaded to your phone. It’s for the sake of science.

While being a little cheeky, get a glimpse into your date’s sense of humour.

28. By the way, do you like to text or call?

What are the chances? Perhaps your date despises texting as much as you do and would like to converse on the phone or Facetime instead? You won’t know unless you ask.

29. I can’t get over how adorable you looked in [piece of clothing they wore on your last date.

This is a guaranteed method to make your date feel good about themselves and encourage them to text you first.

30. Animated GIF

If you’re extremely bashful and can’t think of anything to say, type “hello” into the GIF search field and see what comes up. Send a charming animated GIF. It may not be one of the best texting conversation starters, but it’ll be better than a “hello.”

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