How Not To Be Boring (With Women)!

How Not To Be Boring

Whether you’ve just met or are courting or dating a girl or in a long term relationship, you’ll want to know how not to be boring.

Boring is basically the number one reason women lose interest.

Woah, right?

And since learning how not to be boring is something any man can do, why not you!

Just Met

Boring is predictability.

Sure, later on she’ll want to know you’re reliable but make no mistake unpredictable and reliable can coincide.

How not to be boring when meeting a girl starts by throwing her off her guard.

Women have certain expectations about men and evaluate you in a fraction of a second.

It’s part of our survival and safety mechanism.

We need to determine tout-de-suit if you’re safe or unsafe.

But along with that come other automatic assumptions.

So the best way to intrigue a woman you’ve just met is to counter those expectations.


If you’re a good looking Chad or Tyrone, you won’t want to approach her with the attitude you know you’re a fine physical specimen.

Instead of being arrogant, you’d surprise her with something like, “I know I’m just an ugly bum but you look like a nice girl who goes for personality.” Mischievous grin.

But Anna, what if I’m ugly, geeky, gangly, pimply, short, fat or smelly?

First, don’t be smelly.

Second, for any real or perceived physical flaw, act like it’s your hottest trait.

Wait, what?

You read that right, if you go in with unexpectedly ridiculous confidence about your appearance, you’ll throw her off guard.

She’s not expecting a less than average attractive man to be super confident about his appearance.

So, you might say, “I know you’re probably intimidated by my rugged good looks, but I assure you I’m not a bad boy.” Wink.

Yes, yes, you do have to develop cajones of steel to pull this off, but these are the guys who get girls who are physically out of their league.

Watch Get a Girl Out of Your League

Bottom line: If you don’t know her at all or don’t know her well, come out of the gate with something you know will be unexpected.

Guaranteed if she’s worth half her weight in salt she’ll at least have a laugh!

Key point!

Confident, cheeky self-deprecating humour is attractive if you’re not serious about the flaw and shows wit, a subtle sign of intelligence.


Laughter releases feel good hormones she associates with being with you! #doublewhammy

Texting / Communicating Stage

Once you’ve got her in the communication loop, you’ll want to continue to stand out from the other dud orbiters she’s entertaining.

Again, you do this by continuing to be unpredictable.

This means not texting every morning to say, “Hey, beautiful.” Or “Good morning, pretty lady.”

Wait, what?

Noooo, not yet.

She has not earned this level of attention and it will not only be boring but it will feel smothering to her.

Instead, you send random messages or odd questions, funny memes, photos of things that made you think of her and/or a pre-recorded voice note—not a phone call.

I’ve given examples of these my video __ which I’ll link at end.

Key point!

Unless she’s over 40, and not an introvert, she likely won’t want to talk on the phone.

But a ladybird of any age doesn’t feel put on the spot by receiving a voice note.

I’ve said elsewhere to call her, which is okay as long as you’re not expecting to actually speak with her. (Though I’d choose voice note over phone call if she’s under 25 or an introvert.)

Key point!

Never never try to FaceTime or Snapchat with her without prior arrangement!

Unless she’s an Ashley or Jessica, she needs time to prep her face before putting it on camera for you. Women wear makeup for a reason, y’all.

Rule of thumb 1:

Initiate 30% of the time at the beginning and 50% after she’s committed to you in some formal way. For example: as your exclusive squeeze or girlfriend.

Rule of thumb 2:

Be the first to end the conversation 70% of the time. Always. Exiting doesn’t mean ghosting the convo.

Wingmam motto: Always leave them wanting more.

Dating & LTRs

Once you’ve got her in your lair, you’ll want to continue to seduce her mind and heart, not just her body.

Again, how not to be boring is always about providing the unexpected. But in good ways.

Bad ways:

  • Cancelling or not showing up to a date.
  • Ignoring texts/calls for extended periods of time.
  • Lying, cheating, being a dick.

Good ways:

  • Romantic but ridiculous over the top announcement on Craigslist that doesn’t totally out her.
  • Surprise date at a new location.
  • Planned event—she knows the date but not the details—focusing on her love language.

Watch my video on Love Languages.

How not to be boring is all about doing your part to keep the spark alive because boring leads to looking elsewhere for excitement and that’s no good.

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