Text message flirting guidelines

A common request I receive is for help and guidance on texting a new potential suitor. Usually I receive such requests from men, as women tend to more readily ask their friends for advice, but occasionally I get such requests from women too. Sometimes I get asked outright to write a text from scratch for someone, although I will explain shortly why this doesn’t actually help in the long run.

Due to this demand, I have decided to compile a list of general guidelines for texting someone you have recently met and acquired the phone number of. These guidelines are most relevant for the beginning stages of dating. After knowing someone for a while and getting past the initial pressure of texting someone new, you won’t have to worry about these concepts, although they are still useful to keep in mind when texting in a relationship…

First thoughts are usually the best:

Have you ever sat there staring at your phone, agonising over what to write, modifying your drafts hundreds of times, asking around your close friends for creative input and then agonising some more before finally sending something similar to what you had in the first place? More often than not, what you immediately think of when crafting a text message is the best option. Overanalyses kills creative flow!

Further on from this point, less thought is generally better. An attractive person is usually a busy person and hence will send texts whilst on the move or just before heading off to do something. Sending a message quickly with your first thoughts has two benefits: it conveys that you have a busy lifestyle in the way you have written the message and it also prevents overthinking whether what you wrote was the best possible message, or whether the other person will reply!

Keep it short:

One of the biggest turnoffs in dating, whether you are male or female, is being needy. Nothing displays neediness more than a long essay in text message form, that clearly took considerable time to compose. Keep your message as short as possible while still saying what you want to say.

Amount and frequency:

A good rule of thumb for how long and frequent your text messages should be is to do roughly what the person you are text flirting with does. By that I mean, if they are taking five or six hours to reply to each text, you generally want to be hitting the same frequency. Don’t be ruthless with this if a quicker response seems reasonable but resist the urge to get excited upon receiving a text message and respond in an instant if they aren’t doing the same.

This does not contradict my earlier point of replying with your first thoughts. Read the text message, put your phone away and then reply from scratch when you want to. If you are receiving immediate replies from them, consider making them wait a bit for your next message. Nothing builds tension and intrigue more than them waiting, within reason, for your reply. You will be on their mind all day!

Keep the interaction exciting:

Nothing kills interest more than a mundane and prolonged text exchange. Yes you will be building rapport by doing this but text is not the best way to achieve this; you want to do that in person! Make sure every message you send is exciting and interesting. You want them to be smiling and giggling when they receive your message whenever possible!

If you are being asked in-depth rapport style questions then make them wait until they meet you to find out more and handle the question with a cocky and funny response in the meantime. They are only asking such questions in the first place to ensure the interaction continues and to make sure you know they are interested.

Text messages are one of the easiest forms of communication to take out of context, so don’t take everything literally and don’t jump to any conclusions about anything they have written.

Make sure the interaction is always progressing:

Despite being an easy and quick way to flirt with someone, texting can only get you so far. What you really want to be doing is leading up to a phone call or an in-person meet-up.

An easy way to progress to meeting in real life is to casually introduce the prospect, once again in a fun and flirty way. I’ll give an example, which I’m sure is something similar to what I sent my girlfriend initially to suggest we meet up in person:

“Hey. [response to their last message]. Well I think I’ve finally assured myself that you’re not a boogieman so I’ll let you come and hang out with me sometime next week. 🙂 What’s your schedule like?”

There are several other points I get asked about, such as whether to text or call and how to introduce call-back humour. For now though, keep in mind that you should never worry about something as trivial as a text message and remember that whatever you are sending, if they are replying, they are indeed interested! 🙂

Much love,


18 replies
  1. dave
    dave says:

    i know what ya mean bout not texting too much. i’ve got this girl who texts me like everyday asking what i’m up to. sometimes just that. what would be the best response to that? thanks.

  2. Christy Benson
    Christy Benson says:

    So I’ve got this regular from the coffee shop who hijacked my number and now texts me constantly. How do I politely say that the only reason I’m nice to him while serving him coffee is because I’m paiiiiid to be nice? Hmm.

  3. Samuel McCrohan
    Samuel McCrohan says:

    Hey Dave, quite a desireable problem ai! 🙂
    Like I mentioned in the article, a girl will text you things like that purely because she is interested in you. I’ve had girls text like this in the past and without being overly harsh, it’s often because they can’t think of anything more imaginative to keep the conversation flowing.
    On a more practical note, make sure your life is busy and interesting so you’ll always genuinely have something to reply to that question with. If you haven’t yet and want to meet up with this girl though, it also seems the time is definitely now. 🙂
    Good luck and thanks for your comment,

  4. Samuel McCrohan
    Samuel McCrohan says:

    Ah my dear Christy,
    I’m interested as to how a customer ‘hijacks’ one’s number! I’m shocked you’re only nice because you’re paid to be anyway… I hope that’s not the reason you’re oh so nice to me!! 🙂 If you don’t actually want to tell him you’re not interested, I guess the only way to give him the message is to not reply to his texts. A bit of Christy-spit in his coffee might work too… actually, he might like that! 🙂

  5. Heidi
    Heidi says:

    I certainly did reply to Sam’s witty message (as they frequently are, even now after two years of being together!) and I definitely would say I made a good decision in doing so : )

    The point that sparked the most interest for me is the amount and frequency of texting. When I first met Sam I was so used to texting back and fourth with my friends many times throughout the day, and I would try and reply almost instantly to any message I was sent. I therefore found it very difficult when I realised Sam would take a painstakingly long time to reply to my messages. Even though I found this hard and would have to restrain myself from not texting back too soon, I found the unknown exciting. When I eventually did receive a message from him, they would always make me smile : ) I loved challenge of thinking about an equally good reply…although mine rarely were!

    Another point I would like to add is the use of language in a text. I would previously write all my texts in shorthand, which I believe many people did and still do. I have changed this habit however and now write full sentences and use correct English grammar. The main reason for this is so that texts are legible and cannot be misinterpreted. What do you think about this Sam?

  6. Samuel McCrohan
    Samuel McCrohan says:

    Aww you’re such a sweetie! 🙂 Your texts always make me smile too! 🙂
    It’s funny you’ve mentioned the grammar and spelling point, as it was in my extended notes, that I cut out of the final article. I think it is largely a personal thing (which is why I didn’t include it) but to me it does convey a certain level of intelligence to write correctly whilst on the other hand, text abbreviations convey a certain lack of intelligence (although it’s not necessarily true).
    Thankyou for your contribution babycakes, 🙂 xxx

  7. Christina
    Christina says:

    Sam I’m very impressed with all the advice and I do definately agree with the majority of the points made. I did however, take a completely different approach and remember saying to my boyfriend of now three years at the point of number exchange, “Don’t take hours responding to my texts if you like me because if you like me you’ll text and if you don’t you wont, the space inbetween doesnt bother me!” It may sound to the point but I thought I was quite tactful and said it in a funny way and it seemed to work as we were frantically texting and meeting up practically every day over the summer, it was so exciting and I wasn’t any less thrilled by the fast pace but all the more excited as they were all cheeky and very funny texts (yes im hilairious) 🙂 I guess every situation is different and I think the fast pace only worked because the texts were more exciting than needy, I just felt like we wanted each other more and we didnt let the rules get in the way

    P.S He didn’t however, serenade me on his knees with “Under the Sea!” so extra points were definately lost there xx

  8. Samuel McCrohan
    Samuel McCrohan says:

    Hey Christina,
    haha never underestimate the power of Sebastian the Crab (despite the fact he’s a lobster)!!
    That’s a great point. I presume it worked so well because it was mutual. Although you had laid down the Christina law :), it seems he was equally keen and excited with the many texts and seeing each other lots. You hit the nail on the head when you said that it was all exciting rather than needy. How did you guys meet out of interest?
    Thanks for your comment my dear and I hope you like the website, 🙂

  9. RaiulBaztepo
    RaiulBaztepo says:

    Very Interesting post! Thank you for such interesting resource!
    PS: Sorry for my bad english, I’v just started to learn this language 😉
    See you!
    Your, Raiul Baztepo

  10. Analeese
    Analeese says:

    Hello Sam,
    I have to say a lot of this article really infuriated me!
    When it comes to sending text messages I think you are thinking about it way too much.
    Let me tell inquisitive daters reading this – for goodness sake, if you want to text someone just text them! Don’t play games! If you wait six hours or so every time you send a text, in my view, you’re just showing that you’re either too inconsiderate or lazy to make time to reply or you don’t really like the person you are texting all that much.
    If you want to text back immediately and frequently then just do it. If you don’t then you’ll just be hiding your true personality traits. If the receiver of the texts finds this annoying then this is a good hint that a relationship will not work – you don’t work in the same way. The same applies if you usually take a long time replying to texts simply because you are busy – if the receiver can’t cope with your hectic lifestyle then a relationship with them would not work.

    Of course this is simply my opinion and we can see through Heidi’s post that there are some girls who do not agree with me, but through my experience talking to girl friends this is the main consensus!

    • Samuel McCrohan
      Samuel McCrohan says:

      Hey Analeese,

      I appreciate what you are saying but it simply isn’t that easy for a lot of guys. I get a countless number of e-mails from students every week purporting text-related problems that are so trivial to the actual bonding of two people but have ruined potentially fulfilling relationships.

      There are so many counter-productive things that guys and girls do with the aim of creating attraction and rapport, mainly as a direct result of social conditioning and more specifically the whole pursuer/prize agenda of dating. Texting is a sad way for a relationship to be halted, before it’s even been given a chance.

      I always advocate acting genuinely and with integrity but simply put, a lot of guys haven’t been taught the best ways to convey their personalities to attract a woman and this goes for texting too. To be honest I could have had just one tip to trump this whole article… ‘Get the person you like on the phone and arrange a meet-up in real life’ and this is what the article was leading towards, in a way that would be easy for someone whom texting is not too far outside their comfort zone, whereas other methods would be.

      Thanks for your comment… I like women with strong opinions! 🙂

      Sam x

  11. claire
    claire says:

    how do i get my partner to be more affectionate?… he was very much affectionate through texts , emails and such up until 6 months of dating, and i don’t doubt the feelings he has for me are the same as what i feel for him but i just like to be flirty and affectionate to keep things fun and kicking. I want to approach him about it without it sounding like im criticising him, but i have tried to spur him on but i hasn’t really gotten us anywhere. I would really appreciate your advice

    • Samuel McCrohan
      Samuel McCrohan says:

      Hey Claire,

      This sort of scenario is extremely common in relationships and in fact six months is a common waypoint for it to occur.

      As a relationship progresses, it is common for either or both people in the relationship to become subconsciously complacent. It could be the case that as your boyfriend has become more comfortable and secure in the relationship, he feels less of a need to continually do things to attract or impress you.

      As I mentioned, this is usually a subconscious development and therefore does not necessarily dictate a change in his actual feelings, like you said. In other words, if your boyfriend genuinely thought he might lose you, he would probably amp up the affection and flirting once more. This isn’t to say that you should convey in any way that he might lose you, but is worth thinking about so you can work out how any changes really came about.

      Verbalising to your boyfriend that you love it when he’s affectionate and flirty with you could work, depending on his personality and mood at the time. As you say, you don’t want to come across as critical, so if you do decide to be direct, make sure you focus on things you would like him to do, rather than things you want him to stop doing!

      The fact that you say he has acted in this affectionate and flirty way in the past means that you can very easily encourage the same behaviour again by taking the lead. Think back to the sort of interactions you are reminiscing and think how you could get a similar variation of rapport going again.

      One idea could be to send role-play style text messages and get him to play along. Heidi and I do this every now and again, as it is one way to remind us not to let the relationship become too serious or boring.

      There are obviously loads of other ideas that would have a similar effect, but the main thing is to give him a REASON to be affectionate and flirty with you and then I’m sure he will naturally adapt. 🙂

      Thanks for writing,


  12. Michael
    Michael says:

    Hello, Sam!!

    I’ve been texting this girl back and forth and we started out right off the bat, flirting and even getting into the more graphic details, even sending a couple of pics 🙂 but, the only question I have is…there must be a framework, I feel like I am starting to run out of clever things to say, and advancing the relationship…I feel like I’m losing the interest, what kind of questions can I ask to reignite the fire, because I got all sorts of text messages telling me all of the dirty things she wants to do to me, and what not, and we’re probably meeting up tomorrow, so, I need something like a checklist I can follow before I send every text, and that way, close the deal..



    • Samuel McCrohan
      Samuel McCrohan says:

      Hey Mike,

      There are specific structures you can use for writing text messages but it is more important to simply ask “what will this text achieve?” before sending each one. The answer to that question will differ depending on how far the relationship has developed so far. Remember to always progress the interactions and the relationship as a whole.

      A text message can be something to spike attraction, make her smile and get her thinking about you. It can also be used to test her level of compliance or comfort (seeing how she responds to a sexually teasing text for example). It sounds like you are already doing both of those, so the only thing to ensure is that you don’t overdo it… Keep her wanting more!

      A lot of people text just for the sake of it, or simply to prolong or force the conversation. If you have already arranged to meet up then only use the texting in moderation to get her excited about meeting up. You don’t need to continually have something clever to say. Keep any questions as light, funny and with a judged amount of sexual suggestion and save any deep or meaningful questions for when you see each other in person. 🙂

      Thanks for reading,


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