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How To Start A Conversation With A Woman Over Text That Leads To A Date

How To Start A Conversation With A Woman Over Text That Leads To A Date

How To Start A Conversation With A Woman Over Text That Leads To A Date

If you’re wondering how to start a conversation with a woman over text, you’re not alone.

Texting is the most important and popular medium we have for flirting.

Think about it.

Everything takes place via text.

Initial messages of affection, asking a woman out, courting her, date follow-up — literally everything.

With that being the case if you’re not a good texter you have zero chance of ever winning a woman’s heart.

How to start a conversation with a woman over text

With so much of the courting done via text, it’s vital that you know how to woo a woman online before you do so IRL.

In this article, we’ll teach you how to start a conversation with a woman over text.

However, online conversations are shallow and in no way take the place of phone conversation or a real life date.

With that said, this article won’t just teach you how to chat online, but how to effectively steer the conversation towards asking a woman out.

How To Start A Conversation With A Woman Over Text

Whip out that phone and make sure your fingers are at the ready.

Here are six actionable steps you can take right now to chat it up with that beautiful woman you met at the bar, yoga, rock climbing, the beach, on Tinder, etc.

1) Make An Entrance

The first message you send is your chance to make a second first impression.

It doesn’t matter how you two met, you’ve never met over text messages. How you message her will set the tone for the conversation to come.

So how do you want to play it?

Keep it simple.

She doesn’t have your number so simply shoot her a message telling her whose number this is.

If you got her number from an app say something like:

Hey Sam


(That cute guy from Tinder with the nice face… your words)

Such a message clearly sets a flirty tone.

And hey, it doesn’t matter if she said your face was symmetrical or not, what matters is that she knows you mean business.

The message above is pretty generic. Ideally you write something that touches on something you two were talking about before you got her number.

Let’s say that you met in person and had a more in-depth chat than an app might allow for. Remind her that you’re:

“Hey Jen

It’s Steve, that earthy hiker guy from Dave’s party”

If you two had a laugh or riffed on something during your initial chat, this first message should touch on that positive moment from your first interaction. In this imagined scenario the guy sending the message clearly bonded with the woman he’s texting over how much he or they both like hiking. 

For an even bolder move, don’t even tell her who you are.

Simply pick the conversation up from where you left it.


“I still can’t believe you’ve never had a lox bagel. We’re gonna have to remedy that.”

2) Pick Up Where Things Left Off

It can be difficult to keep the vibe going via texts.

This is why you’re going to cheat.

Instead of starting from scratch, talk to her as if the conversation never stopped.

What were you guys really vibing on before you asked for her number?

Were you talking about the amazing Pitbull she just adopted, the fact that John Mayer is the most underrated lyricist in music, or how much you two miss Lunchables?

How to start a conversation with a woman over text

Whatever the case might be simply start messaging her about that conversation.

Milk it until it’s run dry.

But here’s the thing.

Every conversation has its limit.

There’s only so much you can say about how overrated Beyonce is before the conversation goes stale.

After a few more exchanges you should be ready to take the conversation from online to IRL.

By this point you should have built up enough rapport to be able to:

1) ask her out

2) have her say yes

3) know what she’s into so you can use a compelling TDL

3) Ask Her Out

I’ve said it before but I’ll say it again.

Dating apps aren’t actually for dating.

As Ellen Fisher — anthropologist, senior research fellow, at The Kinsey Institute, and all-around badass — says, people have dating apps all wrong:

The bottom line is these are not dating sites, they’re introducing sites.”

“Dating apps” is a misnomer.

You don’t actually date anyone on these apps, rather you’re introduced to them.

The same logic applies to texting.

Sending messages whether on a dating app or via text is shallow.

You’re missing out on non-verbal queues, smells, and nuances that you can only get in an IRL date.

That said, you want to steer the conversation towards asking her out throughout your conversation.

Base the first date idea on whatever you two have been chatting about.

If you’ve been vibing on biking, suggest going for a scenic bike ride. If you’re both wine enthusiasts invite her for a picnic at the beach that includes an aged bottle of quality vino.

When you do finally ask her out, use a TDL.

TDL stands for time, date, location.

A TDL is your lodestar, let it guide you to the promised land.

A high-quality TDL looks something like this:

“Liz! You, me, bowling and arcade at Shoots & Scores this Friday at 7pm. Bring your A game.”

We have the time (7pm), the date (Friday), and the location/activity (bowling/arcade).

By outlining all the details of the date you’re giving her a concrete offer she can either accept or reject.

There is perhaps one alteration you might want to make to the date request.

Depending on the relationship you already have with this woman she may not 100% understand that you’re asking her on a date.  If you met via Tinder and Bumble you may not have to explicitly call it a date. However, if you’re friends or acquaintances you may want to make it crystal clear.

To do so simply tell her that you are in fact asking her on a date.

Something like, “Let’s go on a date this Friday at Shoots & Scores…” should do the trick.

Now that you know how to use a TDL it’s time to ask her out.

However you might be thinking, why so soon?

You’ve got to strike while the iron is hot. Wait too long and the fledgling flame won’t be hot enough anymore.

Also, realize that 50% of Tinder users have never dated a match.

This is because most are too *fill in the blank* to actually ask a woman out.

Luckily you’re not one of those people.

While you still have momentum ask her on a date that is too fun and easy to reject.

The closer the date is to her home and the more interesting the date idea is the more likely it is that she’ll accept.

Making a woman do something she isn’t into or driving 30 minutes to see you is a guaranteed way to be rejected.

4) If She Rejects Your TDL

Rejections are bound to happen.

This is how to behave when she rejects you.

Firstly, address her objections.

Perhaps she writes you saying:

“Haha, that sounds great, but I have to work late that day.”

The problem is the timing and/or day. Simply change the day for either one prior or after the original TDL and ask her again.

In an ideal world, she would’ve responded, “Haha, that sounds great, but I have to work late that day. Why not Thursday?”

But this rarely happens, even if she’s into you.

However, perhaps her rejection is even vaguer than the one above:

“Sorry I can’t.”

If this is the case, voice your disappointment before asking her on another TDL a few days later.

Tell her, “Bummer, I was really looking forward to teaching you a thing or two. I’ll bother you again in a few days.”

If she rejects your TDL a few times be sure to change up the date idea. Repeatedly asking someone to go on the same date will get stale. Ask her on a completely different date the second or third time around.

If she ghosts you, ask her on three TDLs before calling it quits.

5) Keep Pre-Date Chat To A Minimum

She’s finally agreed to go out with you.

Hell yes.

Now it’s time to keep your fingers away from the keyboard.

But why you ask? She likes me why not keep the good times rollin’.

Because chatting it up after a date’s been agreed upon is like filling yourself up with bread before the steak arrives.

Any interaction via text is superficial. It takes the mystery away from meeting in person and deflates any sexual tension you had been building.

Between the TDL and date, you should be silent.

That is of course until the day of or the day prior when you text her again to confirm the date.

6) If She Needs To Know You A Bit Better Before Going Out

When you ask her out with that first TDL there are many reasons she might reject it.

One reason is that she just doesn’t know you that well.

If that’s the case you’ll have to invest more time kibitzing online before meeting IRL.

To ensure this conversation doesn’t drag on and isn’t horribly cliche here’s what you’ll do.

Answer Her Questions

Continue to talk about whatever you two were vibing on (make sure this convo lasts less than 20 text exchanges). 

Any most of her questions. If there’s a particularly humorous answer you have for one of her questions tell her that you’ll only answer that on the first date. Use it as an incentive while reminding her that your ultimate goal is meeting in person.

Don’t ask her many questions if any at all. Save these for the first date. Focusing the attention on her will make you come off as super interested in her. Showing genuine interest is always hot.

Let Her Stalk You

She hasn’t yet agreed to the date because she doesn’t feel comfortable enough.

Address her concerns by allowing her to feel as though she knows you by providing her with your IG and FB information.

Letting her stalk away will address any concerns she might have about what you look like, what you do, your hobbies, etc.

Go On a Virtual Date

If you can tell she isn’t about to agree on a date anytime soon you can ask her on a 15-minute virtual date.

Share a glass of wine or beer and simply chat it up for 15-20 minutes.

Ask Her Out Again

After all these steps have been satisfied it’s time to ask her out again.

Now that you know more about her be sure to use a TDL that involves a date idea you know she’ll love.

Also make sure that the date is close to her home or place of work, brief, and fun.

7) MegaDate

You shouldn’t have to invest so much time trying to get a complete stranger to go out with you.

Avoid spending hours texting back and forth with one woman you don’t even know by MegaDating.

MegaDating involves going out with various women at the same time.

It means leveraging social media, dating apps, friends, etc. to find suitable single women to date.

When you’re dating so many women at the same time, you won’t get hung up or waste time trying to convince a reluctant stranger to go out.

If you’re not sure how to get started MegaDating, just talk to me or one of my colleagues and I’ll let you in on the secrets of how to score more dates with super compatible women. 

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