Dating and Texting: Overcoming Worst-Case Scenarios

Here’s how to successfully handle awkward dating-and-texting situations.

For a lot of our clients, finding the right vibe and style when texting a woman can be tough.

On one hand, they don’t want to show themselves as overeager by sending too many texts too soon.

On the other hand, they don’t want to be ghosted because they waited too long or said the wrong thing.

With the right skills and knowledge, however, texting won’t feel like you’re walking a tight rope.

In fact, it will feel natural, fun, and exciting.

Best of all, it will feel that way for her, too, and she’ll be the one excitedly checking her phone waiting for the next text from you.

So what is this magical mix of skills and knowledge for dating and texting?

Read on to find out!

Skill #1: Hone Your Low-Pressure Texting Vibe

Just like all parts of dating, successful texting begins with the turn-on equation of Relaxation + Excitement = Turn-On.

You can think of the X + X part of the equation in a number of different ways depending on your vibe.

Maybe it’s Chill + Fun, Open + Engaged, Laid-back + Playful — whatever it is, you want to bring an easeful curiosity and sense of fun to the conversation.

The great thing is when you’re enjoying yourself and exploring a connection, there’s no need to be on guard, defensive, or hesitant.

Part of maintaining that chill vibe is exploring the potential for chemistry without pressure — on yourself or on her.

This includes knowing what to do if she’s not engaging with you on the same level (we’ll get to that soon).

By staying focused on your search for women who are warm and open to you, it will be easier to accept if things don’t work out.

You’ll be able to let the conversation — and the stalled relationship — go without getting too down on yourself.

Skill #2: Tap into Your Humorous Headspace

You should be someone she feels excited to see. The way you do this is by being fun and having fun.

Believe it or not, having fun” is a skill.

One way to discover and build your humorous headspace is by watching stand-up comedy or other fun and funny things.

By learning how others appreciate and express humor, you can play with it as well and find your own fun, creative headspace over time.

This discovery will then filter into your text messages. They’ll be more entertaining, conversational, and will earn more responses.

For an example of taking this to the limit, check out this oldie-but-a-goodie article from Nick Notas.

He hijacks his friend’s OkCupid account (which wasn’t getting lots of engagement) and live-chats with a woman to show how playful you can be.

Guess what? The woman was totally into it because it was fun and silly.

Dating and Texting Scenarios

Once you feel confident with your new skills, overcoming worst-case texting scenarios becomes much easier.

That said, there are some tricky situations that may have you wondering how to move forward.

Let’s look at how you can handle some of the most commonly awkward texting scenarios.

“I Don’t Know What or When to Text after Our First Date.”

Once you’re back home from your first date, your next text to her can be that same day/night, depending on the time of your date.

Option 1

If she took a cab or made her own way home, you can text something like:

“I loved spending time with you tonight. Did you get home safe?”

Option 2

If you took her home (so you, therefore, know she arrived safely, unless one or both of you was abducted by aliens on the spot), you can simply say that you enjoyed spending time with her.

Optionally mention something funny or noteworthy about the date if you have something in mind.

It’s not necessary to wait an arbitrary number of days to text her again if you enjoyed yourselves.

The idea is to keep the relationship warm by engaging with her.

She Hasn’t Responded

Give her a day, and then send a fun text (more on that below). She will usually respond.

If you still don’t hear anything, wait two days and then send one more fun text.

This gives her the chance to respond if she had the craziest week of her life, which sometimes happens (late-night chess matches are no joke).

After that, let it go.

Here are some examples and options of “fun” texts that have worked for previous clients.

Option 1

Send a picture of the gorgeous day outside along with a positive, low-key message like…

“Hey so-and-so, it’s a beautiful day! Sending good vibes your way.”

If it’s rainy and you don’t like the rain, send her an image of your rainy window with a thoughtful caption like…

“Hey, hope you’re keeping cozy and dry.”

Option 2

If the weather is neither here nor there, try sending her a photo of something sweet and/or silly that you found and think she’d like.

It’s even better if the message involves one of her hobbies or passions.

For instance, if the woman you like is a rock climbing fan, you could text her the recent story about the climber who scaled El Capitan without ropes.

Attach a light message — “Saw this and thought of you!” — for added effect.

She Responds by Saying, “I’m Busy,” and Doesn’t Suggest an Alternative

Key into what she’s busy with, and engage.

Big events — like traveling, moving, changing jobs, or being a bridesmaid in an upcoming wedding — are big deals.

These types of events can get very overwhelming and stressful. For her, going on a date is not as critical as big life responsibilities and changes.

So, if a big event is the reason she’s busy, there’s no need to plan a date.

Instead, try the following low-key texts.

Option 1

Demonstrate your understanding nature by texting a message like…

“Totally get that. I’ll be right here when you’re free.”


“Totally get that. Let me know when you’re free.”

Then comment about where she’s traveling to or being busy or whatever she’s focused on.

Remember to keep it low-pressure, conversational, and fun.

Option 2

You can simply text her things like…

“How did it go today?”


“Do you need anything?”

Being super chivalrous will make her feel special, and make YOU a special person to her.

Stay confident and chill, because anything else is not a good vibe for you and her.

Option 3

Plant seeds of an adventure with you with a message like…

“As soon as you’re done moving, I’m going to reward you with [insert fun date or other treat]!”

This shows that you can always be a fun source of happiness in her life, even if you just met her recently.

Why These Options Work

It’s a good idea to send specific date-focused messages no matter if you’re trying to get a 1st date, 2nd date, or any date after that.

Yet things can get heavy with a bunch of planning and rescheduling texts.

These options allow you to change up your tone in chivalrous, thoughtful ways.

In the end, she’ll either get back to you or she won’t. If she gets back to you, start engaging and working your way toward a date.

If she doesn’t respond, apply your “let it go” skill and move on. You did everything beautifully, and some people just flake out. That’s how it is.

This 3-text rule works because it helps you avoid thinking: “Should I still be texting her!?”

After 3 texts, you know it’s okay to just let it go.

Summary: Texting Is a Dating Skill We Can Help You Build

Communicating via text can be more challenging than through a phone call or face-to-face because you don’t have those vocal or physical ways to check in with the other person.

But if you want to develop a real relationship with someone who you met either on Tinder or in real life, improving your text conversations is key.

Even being a good man doesn’t mean this is a given, though, especially if you come from a history of thinking you have to play games or follow strict arbitrary rules like never sending long texts or always sending good morning/goodnight texts.

You don’t have to do any of that! Next time you’re texting someone, simply follow the guidelines above, and wonderful things are likely to follow.

That said, even the best texts don’t mean that things don’t change last minute before the next date, or even that there will always be a second date.

There are so many factors are at play.


Where to take things from here?

No matter how you slice it, ghosting is prevalent these days.

In a recent survey by the dating app PlentyofFish, 80% of the respondents said they were ghosted by someone they dated or tried to date.

One of the biggest reasons guys believe they’ve been ghosted, they tell us, is because of their text messaging style.

Put simply: They think they’re bad at being funny and low-key in their text messages.

In many cases, we’ll review the messages they sent and there’s plenty of material to work with right at their fingertips.

With just some quick tips and pointers from us during our dating coaching program, clients learn how to avoid being ghosted and instead get positive responses from the women they text.

Plus, they’ve learned how to have confidence in their funny, creative headspace. It’s a double win!

Getting in the right mindset will improve your dating life all around. For more on how to develop a chill, resilient vibe, check out:

If you are ready to tackle the skill of dating like you mean it (because it’s about a LOT more than what’s in this one article), then check out how we can potentially collaborate on that.


About the Author:

Amy has been an Alpha Advocate with us for the past 2 years (she just had her second anniversary!). During calls with potential clients, she carefully listens to each situation and shares her honest thoughts on how each guy can improve his dating life and whether or not our program is the right fit.

phone call / real life / face-to-face / good morning / check-in / text conversations / next time / long texts / real relationship / tinder / play games / goodnight / best friends / good man / last minute / next date / potential partner / second date / wonderful things / next week / cell phone /

Sarah Jones
Sarah Jones
Sarah Jones is founder and CEO of Introverted Alpha; the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of Sarah's 22-page ebook inside the blue box just below.

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