Tips for Flirting Over Text

Texting or chatting now seems to be the go-to way to flirt. But regardless of how long you’ve been doing it, it still feels like uncomfortable and confusing territory. 

Tips for Flirting Over Text

Oftentimes, we feel overly self-conscious about our choice of words, or we over-analyze every emoji we receive. Is this joke too tacky? Is this meme inappropriate? They haven’t replied, do I send a follow-up? I can go on and on with these questions.

In this article, I list down some tips for flirting over text, which, when done properly, actually work. 

  • Starting the Conversation – Just like in real life, first impressions matter. This determines whether you will get a reply or get ignored. So work on your opening. Here are a few things to remember when starting the conversation:
      • Be casual. It’s text, so there’s no reason to be too nervous. You can simply send them a quick question about how their day has been, or something similar, then hope for the best.
      • Set the right tone. If you’re flirting with someone during this quarantine period, maybe you can start by asking them how they’re holding up. Or if it is a person that you’ve known for a while but you’re only starting to flirt with, maybe start with an inside joke, or start a conversation about a topic which you know they will appreciate.
      • Small talk. I know a lot of people don’t like small talk, but if you want to get somewhere, you need to be able to take your initial hello to an actual conversation. Make sure to keep the small talk light and fun. For some more help, check out these text examples at Connection Copilot.
  • Sense of Humour – this plays an even bigger role in flirting over text than it does in real life. Use light sarcasm and a healthy amount of self-deprecation.
      • Sarcasm – if they ask you for example what you’re doing to keep yourself busy during this pandemic, maybe you can say something like “making a list of people I wanna see once this is over,” or something funnier. Make sure to keep the sarcasm light. There’s a difference between being sarcastic and being a jerk.
      • Self-deprecation. This is tricky. Make sure you don’t do this too much. If they ask you what keeps you busy these days, you can casually reply, “counting my sorrows,” followed with a wink or a laugh emoji.
      • Focus on building rapport. Don’t move on to anything else unless you’re sure you’ve already established some rapport. Take it easy.
  • Reading Responses – One important flirting skill to learn, both in text and in real life, is being able to interpret what kind of vibe you’re being given, and then responding appropriately. 
      • If you’re getting a good response, then take the conversation up a notch. They might respond quite positively to your joke and say something like, “you’re funny,” “I haven’t laughed this hard in a while,” then that’s a good sign. But it’s important to take this part slowly. Use innuendos and make subtle remarks instead of actually saying it so as not to freak them out. 
      • Similarly, if you’re not quite getting a positive response, learn to exit gracefully. If they don’t reply to a joke, for example, that could be an indication that they’re not interested. Or if they reply to what you thought was an interesting question with an unenthusiastic one-liner, then it’s time to excuse yourself. Remember to be respectful. Move on.
  • Ending the conversation – You wouldn’t want to put them in a situation where they run out of things to say. Learn to be the person to end (or pause) the conversation, leaving them wanting more. Make them look forward to talking to you again the following day.


Flirting over text can sometimes feel overwhelmingly confusing. The tips above can help. But ultimately, remember, the same rules apply both in text and in real life: be genuine, kind, and respectful. Those things always work.

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