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Texting Tips – Should I Text Her First To Start A Conversation?

So you got her number!


Now what?

Flirt(ext)ation, huh?

couple taking a selfie

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But what if you flare up the flirt(ext)ation flame the wrong way? What if you are still caught up in the age-old quandary of whether you should text her first? What if you get that crucial first text wrong? What if your series of over-thought messages make her feel awkward and uncomfortable? What if history repeats itself and you find yourself in the same rut of a long, frustrating back-and-forth process of figuring if you will ever get the hottie you have now traded over a thousand texts with out on a date? What if your honest intentions of ‘courtship’ become clouded by swathes of ‘casual dating’ in the tech-age? What if your predilection for a pretty future with your crush is ill-equipped to cross the finish-line through your slow sprint to the finish-line vis-à-vis emoji couplings? What if the much-dreaded miscommunication-over-texting seeps into your chats and mars your chances forever?

Suggested read: Which kind of flirt are you? What is your flirting style?

Don’t worry – we have the perfect solution for all your texting dilemmas. We know that texting is quite a pain in many a man’s rear, and understand that the hodgepodge of social skills you have bundled together for your texting needs to be honed into a fine repertoire of skills that shall make you a pro at the art and seal your success with women. Here’s how:

Should I text her?

One of the most perennially haunting questions of dating-scape, the answer to the should I text her quandary is a resounding YES! While it is a given that texting is the new mantra when it comes to dating, many men have got their basics in the realm wrong and for naught!

Scratching your head, eh?

I am hinting at the objective – the motive behind texting. Men tend to have a singular objective for texting women. To build a rapport. Seems like a great objective, no?

Bam – and you accomplish nothing. Reason – your lack of direction behind that horrible, atrocious non-objective that lands you in the realm of random, half-baked, inconsequential, and usually, lame text messages that kill the deal before you can fill in your tender amount.


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Why I deem the supposedly ‘great’ objective a rather ludicrous pseudo-objective that diminishes your chances at success faster than Kim Kardashian drops clothes is because it tends to make you either a clueless, boring guy who shall end up scaring a woman who traded her number with you a string of out-of-the-blue intrusive questions like ‘what’s up’ and ‘how’s it going’ or the endless conversation guy who inundates the girl with a string of equally boring and pointless dialogues that receive a reply either coz the woman in question is bored or just too nice not to send back a response. And while you may think the second breed has unlocked the key to texting and engaging women, let me break the sorry news – both breeds are diabolically annoying and deemed unworthy of ‘dating.’ This is because while the first inane guy shall be wiped off the date-scape in a single stroke, the latter, at some point or the other, shall be too bewildered to find that whilst he was priding himself for finally getting a girl to evince so much interest in him (the 2am string of two hundred odd messages count, no?), the girl landed herself a boyfriend who wasn’t doing the same.

The difference between the guy who gets the girl and our texting goof-ups – their texting approach!

Suggested read: The pick-up lines that shall seal the deal

The secret – a simple, cut-to-the-chase, effective texting system that shall get you the date!

How – by asking for one via text!

No, I haven’t lost it. It works! Text messaging is terrible for establishing rapport, building an emotional connection, getting into a real conversation, transforming a stranger into a girlfriend or lover, showing your personality and qualities. and growing or maintaining attraction. Using texting for any of these things is like using eggs and baking soda for sugar cookies because those ingredients make the other ‘baked thingy’ recipes so scrumptious – but ending up making the output inedible. So, the best thing to do when you want to text a woman is to avoid beating around the bush, engaging in a series of long winded conversations, and instead, be concise and straightforward. Let her see the interesting YOU in person. And for that, send out just a couple of direct messages that are simple, intriguing, and revolve around setting up the date. A fine example-

‘Hey Katie, hope your weekend was good. :) Had the most amazing prawns last night … can still taste’ em. How’s your week looking?’

Why this works – because it is a personal greeting, you remember her name, give some information, and also show consideration. This evinces just the right amount of non-intrusive communication that can spark interest and shall almost always fetch a response. It could be along the lines of:

‘Hey John, thanks. It was good. Uh huh, I love seafood too. Where did you indulge? I am having a lazy week! :P’

And your cue is to sweep in with a ‘save the date’ stroke:

‘Aha, that’s great to know. Why don’t I take you to the place and you can indulge too? Saturday, 2:00 sound cool?’

 And just like that, the response will be an affirmative. See – short, simple, and sweet! :)

Should I text her ‘first?’

Duh uh – YES. Haven’t I drilled that in already? You got her number, you want a date – do the needful!

All the tips you will need

Now that you know what kind of texts work, you need to know the ‘how-to’ about acing it. Knowing something does not necessarily translate into executing it well. The gap between conceiving an idea, researching it, and executing it well are enormous chasms that cannot be bridged with a simplistic model as the above that structures texts around personal greetings, an interesting remark, and a blatant token of interest that is non-intrusive. There’s some major behind-the-scenes action in that formula that you’d need to get in on so you can nail the art. Here are the things you need to know:

1. Faulty mental models aren’t the women’s problem, they are yours


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Men tend to follow senseless models when it comes to texting. They expect women to act, respond, and text back a certain way and when it does not happen, they blame the women for their lack of results. This sort of victim mentality crashes their plane that had just taken off (when he exchanged numbers) right down and burns it to ashes. And why wouldn’t it – imagine getting silly, intrusive questions from a guy you just met at a bar or on the street! The tip – do not expect one half of the world’s population to change to accommodate what you think is the befitting response to a situation. Kick that faulty mental model to the curb. NOW.

2. Phone numbers are traded a LOT, they don’t mean anything


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Phone numbers are easy. And somehow, this idea just doesn’t get ironed enough. Get it straight, loud and clear guys – phone numbers aren’t a BIG DEAL! If I may put it like this – phone numbers are doled out ever-so-often to a dozen guys! Phone numbers aren’t a promise, they are an opportunity. Use them well.

3. Head to the drawing board to paint the smile you’d want your text to receive


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When you get those coveted digits, you may either have piqued her curiosity enough to make her wait for your buzz or not left too much of an impression to make her remember you. So, remember that you might buz in on her in any situation – a lazy afternoon or a rushed, put-upon, annoying, and wonky work hour! And before you hit send on the message you typed, ask yourself if your text would have made you smile if you received it in any of the above situations or at a point on the spectrum. If the answer is yes, go ahead – I give you a thumbs up. But if the answer is negative, head back to the notes and frame a better one!

Suggested read: 10 things every man MUST know before committing in a relationship

4. Do not shoot the sh*t


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A random, half-baked, non-purposive message, especially from a guy she just made acquaintance with is not going to get you the date. Don’t make her wonder, think or even do immense mental processing over a text. She doesn’t need that and nor do you! Just opt for the simple and straightforward approach that merits an equally simple and spontaneous reply!

5. Keep your eye on the ball


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I have already told you – do not do the messaging in droves. Aimless texting isn’t going to get you anywhere. Talks about the weather, a film or even how her day has been shall get you pigeonholed as an-acquaintance-turning-into-a-friend. You will never get where you want to be. So, if you do not want to miss the mark, aim for it honey!

6. Women love to talk, doesn’t mean squat


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Most men I know assume that if a girl talks to them for long hours or in an endless string of chats, they already know what they are driving at. The real truth is that while you are thinking they know you are interested in them (and somewhere, women DO know), they are thinking I’d like to keep this at friendship. And that’s the story about friendzoning, bitching about girls who gave you the wrong cues (or so you thought), and the bitter reality about killing your progress from a fast-turning valuable friend to a potential lover. So – save the cr*p and get to the point. She will know what you want and will decide if it’s worth a shot!

7. Get the digits by asking for the date, verbatim


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Yes, always propose the date first. Even when you are asking for the number. If she rejects sharing her number, she is, by extension, rejecting all future possibilities with you. So make it known that you seek a date and ask for the coveted digits. Of course, you must rouse her curiosity and pique her interest before you pop the date question. And that isn’t too hard either. Just remember that it is imperative that she knows this and it will make your future texting correspondence infinitely smoother.

8. Use an ice-breaker text


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Breaking the ice with a natural, spontaneous formulaic text I outlined in the introduction allows you a free-flowing range of possibilities later. Do not wait too long before texting her – else you might risk fading into oblivion, building things up in your head, and being awkward and pushing off things for so long that she wonders if and when you are going to text and ruling you out as a potential partner. Cementing the bond when things are still fresh in her mind will work in your favor. Drop a spontaneous ice-breaker text and feel the words spread out as a smile on her face, possibly returned as smileys in her response! 😉

9. The 3-day rule is passe


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The old metric of waiting three days before calling is lame. Trash it. Strike while the iron is hot lest some other bloke beat you to the punch. It is an extension of the previous rule and the maxim is – move faster! But do not appear desperate. Be smooth and swift!

10. Short is sexy


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A rule that holds well for all texts. You aren’t writing a novel. Save yourself and the other person the trouble!

11. Use interesting lingo

woman texting

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This one is a lesson that isn’t as easy to teach. It just helps if you are a quirky person who knows the art of blending in the right dash of color to his texts. And this does not mean an avalanche of emoticons. It just means using language that seems colorful, interesting, and attractive. And the tricks are simple – you don’t have to be a Keats or Marquez. Just using active voice or verbs (say I got this or I napped) and chipping in playful lingo such as ‘scoop you’ instead of the traditional ‘pick you up’ or ‘grab’ and ‘snag’ instead of ‘get’ or ‘have’ are just a few starting points to get you in the mold.

Suggested read: 10 crucial rules for dating your friend’s ex

12. Vary the response frequency


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This is a proven fact that women respond better to men whose response time is unpredictable, within a certain acceptable range. The trick is to not go overboard in either direction lest she auto-reject you, but vary your response time instead of replying two hours later each time. Write her back in ten minutes once and may be an hour later the second time around. Keep her guessing and keep her intrigued.

And that’s all the information you need for flirt(ext)ation! Good luck! :)

Featured image source: Google, copyright-free image under Creative Commons License

Article Name
Should I Text Her First To Start A Conversation
Should I text her first? Should I wait three days to text? To text or not to text - is the REAL question. And we have got the answer right here.
Sejal Parikh

Sejal Parikh

"I'm a hurricane of words but YOU can choose the damage I do to you..."