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Dating with Intention: How Forward Should You Be with Women?

Dating with Intention: How Forward Should You Be with Women?

You’ve probably been taught that hypermasculinity is what it takes to win over a woman.

Men pursue while women leisurely sit back and recline as men do all the courting. Generally speaking, this is how it goes. Sure times have changed as women are now more equal both socially and economically than ever, but when’s the last time a woman sauntered over to you at a bar and bought you a drink?

Men have pursued women for centuries and will continue to do so. A man’s label as the initiator is too snug a fit to shake loose anytime soon. Yet pursuing and being forward don’t have to go hand in hand. You can pursue and not be forward at the same time. In this article, we’ll find that perfect balance.



To rewire your romantic tactics we’ll go back to the basics starting with how you mine dates.

Dating with Intention: How Forward Should You Be with Women?

How to Go On More Dates

What’s the context in which you normally flirt in?

If you flirt at work, at the gym, or at your friend’s 3-year-old’s birthday party, you’re flirting in a delicate space. The aforementioned places aren’t prime flirting venues because they’re all designed for other purposes. 

At work you, well, work. At the gym you pump iron  – not chat with sweaty strangers. However, there are spaces in which flirty free for alls are welcome -dating apps are one of these spaces.

It’s on -my favorite- apps like Hinge, Bumble, Facebook Dating, Tinder, and OkCupid that unabashed flirting is welcomed. If you’re weirded out about the idea of online dating, you’re in the minority.

 In 2017, 40% of new relationships started with an online dating interaction. 

Americans’ attitudes towards online dating have changed quite a bit since Tinder was labeled as a hookup app back in 2013. It’s time to embrace dating apps.

Don’t know how to get started? No worries, I’ve got you covered. Consulting with a buddy for some profile advice is one thing, but turning to a professional wingwoman is another. In my Signature Program I’ll teach you what’s needed to create a compelling online dating profile that is certain to receive likes, but more importantly, I’ll teach you how to use a TDL.

Racking up matches is nice, but if you never meet up with these women, what’s the point?

Dating apps should be used as introductory apps. You don’t date the woman within the app, rather you determine whether or not she’s worthy of a first date. The goal of any dating app is to transition the dynamic from one online to one IRL. To do this you’ll have to ask her out with a time, date, location, otherwise known as a TDL.

Ya see, most women are asked to go on amorphous dates in the undefined future. “Hey wanna go out sometime” is a common refrain heard from dudes women never actually go out with. To ensure a yes or no response you have to frame your request using a TDL.



An example looks like, “Hey Steph, care to get nostalgic with me this Thursday at 7pm at The Fillmore to watch Panic at the Disco?”

Asking her out in such a way requires a yes or no response. It shows her you’re serious about dating her and have put thought into your date idea. Use it each and every time you ask a woman out.

How to Not Get Friendzoned

Ahh yes, the dreaded friendzone. Rightly so, if you’re worried about being too forward you’re also worried about being friendzoned. Playing it too cool may lead her to think you’re not into her and thus relegate you to the friendzone.

Romantic interests turn into friends because of their lack of romantic gestures. As it stands you’re worried about being too forward. You may fear that in order to tone it down you’ll have to act in a completely platonic way towards your lady. This isn’t the case.

A healthy balance between the two involves artfully signaling your interest. This means respectfully yet frequent touching during dates, eliciting emotional reactions, and opening up to each other.

When it comes to accelerating attraction one of the best ways to do this is through physical touch. Early on in the relationship (1st, 2nd, and 3rd dates) it’s important to use touch to build a connection

One move that always works involves offering her your hands. While you two are talking, present your hands to her after a joke or during an emotional moment. If she reaches out to grab your hands, this is a signal of her interest. This type of contact is low-risk yet powerful. 

From here, work your way towards riskier and more revealing touching. Start with her hands and shoulders before touching her lower back and leg. You don’t just have to use your hands to touch her. Playful pokes or bumps are great ways to increase attraction.

How to Avoid Having Dates Stall/Fizzle Out

So you’re crushing it online, have lined-up dates left and right but just can’t seem to score a third or even second date. What gives?

Here are some guidelines to keep in mind for the initial dating period.

First dates should last no longer than an hour and no more than $10 should be spent. Short dates mean you can date many women without spending too much time or money getting to know them.

You don’t need more than an hour to determine whether you like a woman or not. If you didn’t like her, well you only wasted an hour of your time. If you did, then the feeling was mutual and you two are left counting the minutes until you hangout again, thus building tension.



Second dates should be active and free. Active dates are dope. No one likes a cliche coffee date. Instead set out on an adventure together. Go hiking, for a run, a bike ride, yoga in the park, or even a walk around a new part of town. It’s much easier to keep the conversation going and initiate touch when you two are being stimulated by the activity enough to always have fresh material to discuss.

On these first two dates it’s important to touch her frequently and respectfully. Pay close attention to how she reacts to touch. If you feel like you’re being too forward, sit back for a while until she signals her interest with a touch of her own.

How to Get Over Feeling Uncomfortable With Being Forward 

Your nerves are getting the best of you because of your framing.

This isn’t a win or lose situation.

You may be thinking that if you don’t “fill in the blank” this is a failure. Stop that.

Think of this as an opportunity to explore the depth of another human being. This is an emotional exploration in which you’re trying to spelunk through the deepest depths of another insanely nuanced individual. 

This isn’t sexual, it’s emotional. It’s about getting to know her, that’s it. Your sexual expectations are making you act either too aggressive or too aloof. Be interested in who she is and everything else will fall into place.

As your exploration continues you’ll likely find that there’s a bond between the two of you. Touching and becoming sexual will fall into place once this connection is formed.

Are You Unsure of How to Escalate?

Escalation is difficult when you two meet in an active cafe for the first time. Whispers turn to shouting just to get a word across and touching is out of the question being that she’s so far away from you. To make escalation easier choose a date spot that is conducive to touching.

If you’re not forward enough with your touch, consider how you can create dates that incorporate touch naturally. 

For example: rather than a tea date where you have to force physical touch, try planning dates where touch is baked into the activity. Consider things like salsa dancing, jiu jitsu or capoeira classes, etc. That way you don’t have to worry about how you’re going to touch her on the date. Now you can be present and enjoy the physical interaction.



Remember that even the most innocuous touches are good touches. High fives, playful butt bumps, and tapping her far shoulder so she looks away from you are all low-risk ways to touch. Should she enjoy your touch you’ll know about it.

How to Tell When a Woman Wants You to Escalate

Stop reading the menu and start reading her body language.

Has she created a barrier between the two of you or is she more than comfortable permitting you into her personal space? Are her arms crossed or is she leaning forward eating up every word you say? When you offer her your hands does she touch them?

Smiles, giggles, sustained eye contact, and of course having her initiate physical contact are all telltale signs that she’s into you.

Most importantly how does she react when you touch her?

Date Sequencing

It’s important that you sequence your date properly to escalate sexual tension.

A first date should be low-key and less than an hour. Second dates are where you want to be physically active. No dinner dates please! Whatever you do avoid boring, inactive second dates. You need to get her blood and adrenaline pumping on a second date in order to escalate sexual tension.

If you want to kiss her on this date, do it. Just don’t ask if you can.

Instead of asking, if you’re feeling awkward, tell her “I want to kiss you right now” and then watch her reaction. If she smiles, leans in, plays with her hair, or giggles, that’s a go – make your move!

Third dates are for dinner and sexy time. Invite her back to your place after dinner. Sit next to her on the couch and don’t be afraid to pull her in for a passionate kiss. 

Escalate physical touch by moving into petting and eventually sex, unless she says “no.” If she does say “no,” then it’s time to have a conversation about why so you know where you stand!

Are You Ready to Get Frisky?

If so go forth and apply the provided advice. If you feel like you need a bit more insider knowledge, consult with me 1-on-1 via a Zoom conversation. 



It’s here that I’ll impart what women want and how they want it. As both a woman and a dating coach I understand what the women you’re pursuing are thinking while dating you. 

Together we’ll teach you how to become a dating maven, how to date compatible women, and find a woman that is worthy of your awesomeness.

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