The “Playfully Aloof” Messaging Strategy

How to Keep the Dynamic of YOU as the Prize and HER as the Chaser While Texting

Let me be clear – you are not supposed to be initiating messages between dates. You’re not texting “just to talk.” You’re not checking in, seeing how her day is going, or validating her over text.

Instead, you’re using “playfully aloof” responses to react to her, not reach out to her.

What’s the goal of a Playfully Aloof response?

To make her laugh
To be a little confusing
And to give her zero real information

The Formula: Funny (playful) + Confusing + Challenging (aloof) = The Perfect Text

Example of a Playfully Aloof Message

Let’s say it’s boys’ night. She texts you:

Her: “Hey what’s up? What are you guys doing?”
You: “Having a pillow fight and talking about the girls we like… top secret stuff.”

You responded—but didn’t actually tell her anything. And you did it in a way that was playful, light, and mysterious. And the best part – That kind of message doesn’t count as giving her real attention. It doesn’t count as a text from you.

Why Playfully Aloof Responses Work

When a woman wants your attention, she messages you. Hey, it’s not a bad thing. The problem is, when you respond seriously (or logically) you become boring and she loses interest.  And if you’re “attractive” over text, she will want to constantly text you 24-7 to get more VIRTUAL ATTENTION.

Most guys are logical and boring over text. The “better” ones try to be attractive over text—flirty, witty, even romantic. Still not good enough. Why? Because even when you’re attractive over text, she gets too much virtual attention and feels no urgency to see you in real life.

Remember, texting is a low-value time slot. So no matter how good your messages are, if you’re giving her too much access, you’ll end up with:

A long message history. No dates. And a girl who lost interest.

So What’s the Solution?

Playfully Aloof Messages.

  • They don’t satisfy her craving for serious attention
  • They don’t trigger the “things are moving too fast” alarm
  • They don’t make her feel like she has you all figured out
  • They leave her wanting more (which makes her want to show up for the date)

She ends up thinking:

“I just talked to him… but I still feel like I didn’t get anything from him. I guess I’ll have to go on a date to get my fix.”

That’s the goal.

When to Use Silly Messages

  • ONLY when she reaches out to you first
  • NEVER to initiate contact between dates
  • Not to keep conversations going— hit her with one and then disappear

Why This May Feel “Wrong” (But Works)

This may go against what you’ve learned. You’ve probably been taught to be “high value” or “attractive” over text. But even attractive messages give her validation.
And when she gets all your humor and attention virtually, she doesn’t need to see you in person.

Playfully Aloof messages give her a hit… but never the full dose.

What Makes a Great Playfully Aloof Message?

Use this formula:

  • Funny (Playful, random, absurd)
  • Confusing (Doesn’t quite answer her question)
  • Challenging (Withholds real information or gently teases)

Her: “Good morning! How did you sleep?”
You: “mypillow.com… it really works. Use promo code SLEEPYPETE.”

That funny but makes zero sense—and that’s the point. She doesn’t know what to do with it… so she thinks about you more.

Humor Is The Delivery System

If you’re not being a clown, you’ll eventually become her fool. Humor is how you signal:

  • “This isn’t serious”
  • “You don’t have me figured out”
  • “You’re going to have to earn the real version of me”

5 Goals of a Playfully Aloof Message

  1. Avoid long, logical, predictable conversations
  2. Keep things light, playful, and emotionally positive
  3. Save serious attention for the date (where it matters)
  4. Prevent giving her too much validation
  5. Subtly show detachment (aloof) —without ignoring her or seeming butt-hurt

5 Benefits of the Playfully Aloof Message

  1. You come across fun and self-sufficient—happy with or without her
  2. You get credit for responding—without giving away value
  3. You don’t fill up her emotional “tank,” so she wants to see you
  4. You subtly flip the prize/chaser dynamic—without trying too hard
  5. You show you’re not needy, without being rude or cold

Pro Tips:

  • Don’t forward memes— If the meme gets the laugh, you don’t.
  • The shorter the better.
  • Non-sequiturs work great: statements that make no logical sense after her question.
  • Avoid “inside jokes” or callbacks to previous moments—it signals you’re replaying memories instead of creating new ones.
  • Don’t try to be “funny.” Just be silly. Confusion is more powerful than a punchline.

Advanced: The Prize Frame Reversal

You can take Playfully Aloof messages to the next level by reversing her prize frames through humor.

There are 3 common prize frames women subconsciously hold:

  1. She’s the one being chased for love
  2. She’s the one deciding when intimacy happens
  3. She’s the more beautiful one

Now—don’t address these directly. Just use playfully aloof humor to flip the frame:

Her: “You didn’t text me back last night.”
You: “My fan mail got backed up again. You’re lucky you made it to the top of the stack.”

Common Mistake (Client Story)

This past Friday we texted back and forth for about an hour. It went well and we did a ton of catching up. So we set up a date for yesterday to go out and eat. Then about 11am she texts me saying she feels sick and that we may have to do it another time.

Can you spot the mistake he made?

His mistake was filling up her need for his attention by spending an hour texting back and forth.

Although her excuse was that she wasn’t feeling well, the real reason she broke the date was because she felt satisfied and suddenly didn’t need his attention/validation anymore. 

Playfully Aloof After a Breakup (Why This Works Even Better)

When a woman breaks up with you, she expects you to be sad, hurt, or begging.
So when you respond with something silly, lighthearted, and genuinely happy—it drives her crazy (in the right way).

She wants to see you miserable. Instead, she sees you thriving. And that’s when she starts wondering… “Wait—did I lose the prize?”

Final Coaching Notes

  • Silly messages are ONLY used to respond to her messages.
  • They should always feel slightly aloof, like you’re above the conversation—not mean, just playful
  • And above all: Less is More.
    Know when to walk away. Don’t let even the best silly exchange become a long conversation

Key Takeaway

Texting isn’t for connection or exchanging information. It’s for confusion, challenge, and playful misdirection. The real attention? That happens on the date. That’s where you reward her.

Let me be clear…

We are NOT “initiating” any messages to her between dates.

Silly messages are used as a RESPONSE strategy!

OUR MAIN GOAL is to MAKE HER LAUGH AND NOT REVEAL ANY INFORMATION

(aka: be funny & confusing)

For Example: let’s say you are out with the boys (it’s boys night)

Her: Hey what’s up? what are you guys doing?

You: having a pillow fight and talking about the girls we like…top secret stuff

Notice how you responded, but you didn’t actually reveal any information. The message was funny, challenging and slightly confusing. Thus. THIS text message doesn’t count towards giving her attention.

Let’s break this text messagwe down into parts

  • we’re having a pillow fight (funny, silly)
  • talking about the girls we like (mysterious, confusing)
  • top secret stuff (challenging, as in I’m not going to tell you)

The perfect text delivers in all 3 areas: funny, confusing and challenging

Remember, you should always be putting on a CLOWN SHOW….because If you’re not the CLOWN, you’ll end up being HER FOOL


Why Silly Responses?

First off –

You need to realize that the silly messaging response strategy (SMS) is much different than anything being taught and may even go against what you believe would work.

Most guys are boring and logical when messaging girls, so every other dating coach teaches “how to be attractive” over text. While that’s better than being boring, it’s still not the highest level.

So before we get started using the example texts, you need to understand WHY we use the silly messaging strategy (SMS) in the first place.

  • Silly messages don’t trigger her “things are going too fast alarm”
  • Silly messages don’t make her THINK that she’s already has you all figured out
  • Silly messages don’t make her FEEL like you are BORING and predictable.

See, there is a method to the MADNESS

Here’s The Problem: 

When a woman wants your attention, she messages you. Hey, it’s not a bad thing. The problem is, when you respond seriously (or logically) you become boring and she loses interest. 

And if you’re “attractive” over text, she will want to constantly text you 24-7 to get more VIRTUAL ATTENTION.

Remember, texting is a “low value” time slot to give away your time. So whether your texts are boring OR attractive, eventually you’re just left with a long history of messages, and ZERO DATES

Ignoring all of her messages isn’t the solution either. You don’t want to punish her for wanting to hear from you or seem BUTT-HURT

Here’s the good news – 

Even though you will occasionally have to respond to her messages, if you make them silly and confusing, they won’t count TOWARDS  giving her attention.

Common Mistake: (client story) 

This past Friday we texted back and forth for about an hour. It went well and we did a ton of catching up. So we set up a date for yesterday to go out and eat. Then about 11am she texts me saying she feels sick and that we may have to do it another time.

Can you spot the mistake he made?

His mistake was filling up her need for his attention by spending an hour texting back and forth.

Although her excuse was that she wasn’t feeling well, the real reason she broke the date was because she felt satisfied and suddenly didn’t need his attention/validation anymore. 

The Solution: Silly Messages

Engaging in a “silly” exchange allows you to communicate with her without completely satisfying her craving for your attention and validation.

She thinks – 

I know I just heard from him, but I still feel like I need more of his attention.

I didn’t get to tell him all about my bad day at work. Or my argument with Brenda. And I didn’t get to find out what he’s been doing either!

I guess I’ll just have to go out on a date with him to get “my fix”

Real World Examples 

Let’s say it’s her birthday.

Every guy she knows is going to text her “Happy Birthday” and fawn all over her. 

Now, you don’t have to completely ignore her birthday. But you can message her some silly song lyrics: 

Birthdays were the worst days, now we sip champagne when we thirsty!  

Or if she texts you something boring like…

“good morning, how did you sleep?”

You would reply back with something silly like – 

Mypillow.com…. it really works! Use my promo code SLEEPYPETE

If you’re thinking, Chris, that doesn’t make any sense – well, it’s not supposed to.

CONFUSION = Challenge

Your main goal isn’t to answer her question directly or try and be “funny”.

The point is to slightly confuse her.

To throw her off her game. To make her wonder what’s going on and where she stands.

Remember, confusion = challenge (a positive one). If you’re not going to confuse her in a humorous way over text, you always have 2 other options:

  1. change your name to Ramstein and start a cult
  2. buy her a yacht and name it “my princess”

5 Goals of The “Not Serious” Message:

  • Avoid getting roped into long BORING, LOGICAL and PREDICTABLE (BLP) text exchanges
  • Keep things fun, playful and upbeat (show her you’re always in a great mood and avoid getting baited into negativity, “deep talks” or mentor/therapist mode)
  • Silly messages subtly tell her to SAVE the REAL conversation for the date (in a polite way)
  • Not give her any “serious”  attention or validation so she has to go on an actual date with you to get your “serious” attention
  • Show her you can (subtly) walk away by not “trying” hard to keep the conversation going. It allows you to seem a bit aloof and detached, without having to ignore her message. (a negative challenge)

THIS IS NOT AN “ATTRACTION TECHNIQUE”

Warning –

You actually don’t want to seem like you’re trying too hard to make her laugh. Don’t worry about being funny, it’s more important to just be silly.

Even trying to be “attractive” is too much because then she’s going to want to text you EVEN MORE. Then she will get all of your fun and laughs VIRTUALLY and never needs to go see you.

Remember –

Sending an attractive text still counts as a “giving her ATTENTION over text” – whereas a SILLY MESSAGE does not count.

Quick note: do not send her funny memes or forward funny “videos”. (that would be considered traditionally funny) Although they may be funny, it means the meme was funny, not you, I’d rather YOU get the credit by sending your own original silly message.

The 5 Benefits of Silly Messages:

#1) Silly message convey that you are a FUN guy and in a GREAT MOOD (even when she’s not with you) You don’t need her approval to be happy. You are happy WITH or WITHOUT her

#2) You get credit for sending her a message, but it doesn’t count towards giving her SERIOUS (logical) attention. 

#3) It doesn’t fill up her need for your “validation”, making it more likely she will make the effort to come see you in person (for a date) versus keeping your relationship virtual (messaging only) 

#4) Silly messages allow you to position yourself as the prize and make it seem like she is chasing you, without bragging or “trying too hard”

#5) You show you can”walk away” because you’re not trying to have a conversation with her. You’re not trying to “keep it going”. When you send a silly message, it doesn’t matter if you get a response, because unlike when you ask a woman a question, it doesn’t require one.

Bonus: unlike “no contact” silly messages never make you come off like you are butt-hurt or mad at her (pouting) or purposely trying to ignore her or cut back your attention.

Remember, if you ask her too many questions over text it will start to feel like homework (vs. fun) and she will lose interest. Even if she was the one messaging you.

Key Points Explained

Here’s the main takeaway –

Serious attention/validation should ONLY be given when she’s out on a date with you (in person). Not over TEXT. Messaging should be a silly playful world that makes little to no logical sense. 

Also, the shorter the message, the better. Use less words.

You shouldn’t be talking to her, you should be talking through her (to no one in particular). So don’t bring up inside jokes or fun things you guys have done in the past.

If I can easily understand what you wrote, it’s probably not silly enough.

A “non sequitur” is a conversational device, often used for comedic purposes. It is something said that, because of its apparent lack of meaning relative to what preceded it, seems absurd to the point of being humorous or confusing

And remember, LESS is MORE. Know when to end it and walk away. Even though silly messages are very powerful, if you send too many back and forth, she will be filed up with your attention and no longer want to see you in person.

Coaching Point: Silly messages are ONLY used to RESPOND to her messages. You don’t just randomly send her silly messages. You aren’t supposed to be texting her between dates.

And another thing –

I don’t want this to sound the wrong way, but silly messages should give off a slight air of aloofness. They are slightly (ever so slightly) condescending. As if you are above it all. Not in a negative way, you are still being playful. It just comes off slightly aloof and BETTER

Save The Real (Serious) Conversations For The Date

If it’s not a text from her asking you out on a date, then it’s just a message where she’s looking for a HIT of attention.

Nothing wrong with that, but we want to save the “serious attention” for the date. So keep your reply non-serious.

Advanced Class: The Prize Frame Reversal

Silly text messages are great, but if you can also sneak in some “I am the Prize” Humor to take things to the next level. Then they become (S.M.O.S.) Silly Messages On Steroids!

There are 3 “Female Prize Frames” You Need To Reverse with playful humor – for her benefit

1. Who is chasing who for LOVE

2. Who is the one trying to get the other one into BED

3. Who is the more BEAUTIFUL one

Remember, she wants to BELIEVE that you are the PRIZE. It’s not a reach or a struggle because it’s more pleasurable for her if you are the prize!

Coaching Notes:

  • The Silly Message Response Strategy gets harder to do the more she starts liking you. That;s because she will get more and more frustrated (attracted)
  • Remember, when you aren’t being serious, it doesn’t count as giving her attention

Messaging Her After a Breakup

WHEN SHE BREAKS UP WITH YOU, SHE WANTS YOU TO BE MISERABLE, THAT’S WHY SHE CHECKS IN TO SEE IF YOU ARE DOING

So, these funny and confusing messages really make her MAD, because you come across as HAPPY!

And not butt-hurt like the guy who gives her short replies (0k, fine) or ignores her message completely.

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