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How To Be More Assertive with Women, Dating, and Life

How To Be More Assertive with Women, Dating, and Life

There are three things all women love: the Westminster Kennel Club Dog Show, assertive men, and Michael B. Jordan.

Two of these three things you can’t control.

You will never have the symmetrical smile of Jordan or be as strokable as a Best In Show poodle.



That leaves us with the one thing you can in fact control; your assertiveness and how you can leverage it to court women.

Book a 1-on-1 Zoom session to learn how you can be more assertive with women.

Women have cherished assertive men for centuries.

We’ve evolved to appreciate a protective man. A man with confidence, that takes charge, and that can get things done.

Sure even though women no longer rely on men to provide them with physical protection, shelter, and food, the brain has still yet to catch up with culture.

This is why women are still pretty much universally attracted to physically strong, wealthy, and confident men. Until the female brain catches up to culture, women will continue to value these traits over all else.

This is why it’s vitally important that you learn how to be more assertive with women.

In this article we’ll teach you:

— How To Be Assertive To Get a First Date

— How To Be Assertive On a Date

— How To Be Assertive In Between Dates

— How To Be Assertive With Women, In General

— How To Be Assertive Sexually

— How To Be Assertive In Life vs. Following The Herd

How To Be More Assertive With Women

How to Be Assertive To Get a First Date

Being assertive means taking the necessary steps to get what you want.

What this boils down to is pursuing a woman you want to date.

Whether that be through a dating app, a matchmaker, at your friend’s party etc.

The only way to date women is to put work into actually reaching out to them.

If you don’t, someone else will.



If you’re using dating apps and blaming Bumble for getting no matches — then have a professional photographer or dating coach look at your photos.

Don’t have time to mine for dates by yourself, hire a matchmaker.

Do you have a lot of friends? Great, ask them to set you up.

Figure out what your assets are and use them to your advantage. If you sit back and think women will just come to you, other men will take them.

After you’ve tapped your social networks and have found a woman worthy of dating, it’s time to ask her out using a TDL

emlovz Definition: TDL (Time, Date, Location)

A TDL is a concrete date request that has a specified time, date, and location.

E.g. “Stacey! Sunset cocktails at 7, this Thursday, at Porterhouse Brew Co. Are you in?”

A TDL should always be used when asking a woman out because it gives them an opportunity to provide a straightforward yes or no answer to a specified social engagement. Asking her out in such a way always trumps a nebulous request to “go out sometime.”

A TDL is far from a guarantee that she’ll say yes. Be ready to overcome her objections. If she doesn’t respond or says she can’t, follow up at least 3 times before calling it quits.

Demonstrating persistence and having a plan when you ask a woman on a date, is sexy and assertive!

How To Be Assertive On A Date

Being assertive on a date is all about being able to read the signs. To do this, you’ll need to use your emotional intelligence to sense how she feels about you as you delicately turn up the heat.

“Emotional intelligence is the ability to sense, understand, and effectively apply the power and acumen of emotions as a source of human energy, information, connection, and influence.”  — Robert K. Cooper. Ph.D.

One misplaced touch or sexist comment can stamp out any embers you had been fanning. Being assertive doesn’t mean sweeping her off her feet James Bond style and smooching her. Back then such an aggressive style was labeled hot, nowadays we’d label it as sexual harassment.

Here are some ways to heat things up without creeping her out:



— Touch her three times every day (A hug hello, a playful touch during the date, and a goodbye hug)

— Watch how she reacts to your touch

— Touch her when opening doors or when guiding her in a certain direction

— Playfully punch her arm

— Bump her butt with yours

— Offer her your hands when telling a story in the attempt to have her initiate contact

— Talk about weird scars/features on your bodies, then ask if you can touch that weird feature of hers

— Ask to play any game that requires touching each other’s hands

And then there’s my personal favorite, tricking her into holding your hand – just don’t try it with strangers (cause, ya know, COVID).

Another way to be assertive on a date is to be the date navigator.

This entails mapping out the entire date beforehand so that you’re always in control of the situation and can create an awesome date experience.



The plan can be as simple as: brewery > walk through the park > ice cream > walk her to her car/subway.

Once the date is ending you’ll want to use a TDL to ask her out on a second date. Again, ask her on a specific date at a specific time and location. Women don’t want to mess around playing games. She wants to know if you’re into her or not. Asking her out on a second date before the first is over is a clear indication that she’s into you. If she answers yes, you’ll also know where she stands and will prime her for an end-of-date kiss.

Going in for a kiss when the time is right is being assertive.

When you do, don’t ask permission.

If you feel the need to say anything, say “I want to kiss you.”

Then gauge her body language. Make sure to do this while holding eye contact. 

Being Assertive In Between Dates

If a flame is given constant fuel, you’ll smother it.

In between takes is when you’ll want to pull back and take your foot off the accelerator.

I stress this because if you’re TOO assertive you’ll come off as clingy.

Avoid over-texting between dates.

Instead of texting, call.

If she doesn’t answer, don’t leave a long-winded explanation, just leave a voice message that says something like “Hey Victoria, it’s Johnny. Give me a call when you get this.”

The use of commanding language, the mysterious unknown of why you’re calling, and the fact that you picked up the phone to do so are not only assertive, they’re sexy!

Most men are too chicken to do it so you’ll blow your competition out of the water when you do.



Pro Tip: Don’t be like most men – call.

Being assertive in this way subconsciously demonstrates that:

— You can keep her safe

— You’re a leader

— You know what you want and where you’re going

— You’re not afraid to go after it boldly

Whenever you communicate between dates, try to limit it to logistics about your upcoming date. Don’t text without the intent of getting on the date. “How is your day going” is a game killer if I ever saw one.

Give her space to let her wonder about you, then, when you call to schedule or confirm your next date, it will be the validation boost she needs to feel as though she’s lucky that you want to hang out with her again.

How to Be Assertive With Women, In General

Fact: Women love leaders.

Alright, technically it’s not a fact, but it’s just about universally true. The extra in the play standing in the corner occupying the least amount of space will never endear himself to anyone. In this play, we call “You’re Dating Life – Dating Like A Boss” you’re the lead character, ensemble, orchestra, director, and the dude that sells the popcorn out in front.

Being assertive isn’t some ephemeral behavior that you ditch after the first few dates, but one you carry with you throughout your entire relationship.

Women want to know they’ll be safe with you.  

In dating, you can use commanding language to demonstrate your leadership.

Instead of “do you want to” try saying “let’s rendezvous at….”

Instead of “are we still on for coffee?” try saying “Looking forward to seeing you at The Warming Hut at 2pm… if I get there early, how do you take your coffee?”



Commanding language = Language that “assumes the sale” or that assumes she wants you.

Being Assertive Sexually

With the MeToo movement and the current state of affairs, it’s hard to know when to make a sexual move and when that same move might deem you a creep. 

Client Struggle: When Should I Make A Sexual Move?

No one wants to end up like Aziz Ansari. 

You’ll need to walk a fine line when escalating physically. Push too hard and you’re a creep (or worse) don’t push at all and you’ll be friendzoned.

Both labels suck.

So what do you do?

It’s essential to understand when to escalate in a way that is welcomed by the woman you’re wooing.

But that is too big a topic to address in an article.

If this is something you’re dealing with, I’d love to chat with you more about it in a new client intro session.

There, I can share more information about how my coaching program helps men with precisely that.

Being Assertive In Life vs. Following The Herd

Warren Buffett once said…

“Be fearful when others are greedy. Be greedy when others are fearful”

Have you given up on dating during coronavirus because of fear?



Following the herd will usually be a “safe bet,” but likely it won’t get you any further than the next guy.

If you’re content with swiping right on dating apps as your sole method of finding a date, your luck will never change.

But if you’re using dating apps, networking with friends, making approaches in the real world, hiring a matchmaker, working with a dating coach all at the same time – it’s much more likely you’ll find who you’re looking for.

The more you tap your social circles, the more likely you’ll be to find romantic success.

To sail through the doldrums of your love life you’ll have to get creative and be willing to put in the work.

Treat dating the same way you treat learning a new skill.

To fine-tune you’re dating skills you’ll need to:

— Ask yourself why dating matters?

— Figure out what your goal is

— Invest an hour every day into honing your dating skills

— Be willing to push your comfort zone

— Make a commitment to yourself and others in order to be held accountable

— Seem professional help if needed

2020 sucked.

This year, however, is your year.



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