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How to Make a Woman Desire You: A Story From My 100-Date Experiment

How to Make a Woman Desire You: A Story From My 100-Date Experiment

The answer to the question of how to make a woman desire you is easy. It’s confidence. But what does that look like on a date?

Maybe this will help explain: You might remember that several years ago, I conducted a 100-date experiment. Of all the 100 dates I went out on, I remember one guy stood out (besides my current boyfriend, of course!) as being one of the best examples of confidence I’ve seen.

Mind you, he turned out to be a trainwreck (yes, I too have made my fair share of mistakes in the pursuit of love). Still, his confidence kept me intrigued for quite a while. So how did he do it? I’ll break it down. 



Let’s call him “Jake.”

Make Her Laugh

Jake and I met in the middle of a college soccer field at 2 o’clock in the morning. Granted, 2 a.m. is not a time any self-respecting woman should ever meet up with a man — especially one she’s never met. The location, on its own, would have been atypical enough, let alone the actual time of our first date. He was a white guy, about six feet tall and probably 170 pounds. 

What I liked about him right away was that he was clever.

If a man can make me laugh, he immediately places himself in the top 10% of all men I’ve dated. And if his wit is tempered with self-confidence, I am putty in his hands.

Develop your sense of humor, and you’ll see your dating life improve. Humor is an aspect of confidence that not everyone can pull off, so if you’re one of the guys who can, you’ll stand out for sure. 

To be funny, you need two things: presence and good improvisational skills. What I mean by presence is, you have to remain in the moment — not thinking 50 steps ahead and definitely not looking down at your phone. Only by remaining present will you notice things around you that you can make a joke out of. 

Then, of course, you need to think of cool things to say at those moments. That’s where improv skills come in. The good news is, you can learn these skills. If you’re serious about lightening up your personality and letting your sense of humor shine, I suggest you take an improv class. Sounds extreme, but it’s a skill that you’ll use so much more than you think — in dating and even business. Trust me, if you can get comfortable improvising your confidence and ability to make a woman desire you will skyrocket.

Elicit Strong Emotions by Challenging Her

As it turned out, Jake was a writer… and I love writers. Every writer has their own sense of how things are — their own unique perspective on life — and I find that inexhaustibly provocative. 

This guy was all of those things with a dash of daring and fun. Like others who had come before him, we met on OkCupid. He was 24 and a student/server studying the fine art of writing and cynicism. I bet he’s a terrific writer now. Certainly has the wit. 

He really stood out to me because he was the first man, until that point, who had elicited an emotional response within me. I was sexually attracted to him before we had even met. At first, I didn’t understand my response but after reviewing his messages, I can now see exactly why:

He effectively challenged me.

In other words, he never just said what I wanted to hear. If he disagreed with me, he’d say so. He wasn’t trying to please me. On the contrary, he actually had his own opinions and wasn’t afraid to challenge my own beliefs and perspectives. He made me reconsider whether my beliefs and perspectives were indeed correct. By the end, I actually felt like I had to prove something to him!

The lesson here? Don’t be too agreeable when you’re talking to women you’re interested in. Being upfront about who you really are (as long as you’re not super obnoxious) shows that you’re not willing to sacrifice who you are for anyone, which is extremely sexy. 



If you try too hard to be pleasing, you’ll simply be forgettable. But even more than that, especially if you’re looking for a relationship, you want to weed out the women who won’t really like the true “you.” So you need to be yourself as much as possible, even if it seems polarizing. That way, the women who go out with you will likely be more compatible matches.

Build Familiarity over Text

Jake’s approach was confident and funny. He also wasn’t afraid to offend me, which reversed my normal hesitations about meeting a stranger.

The playfulness of the texting built familiarity.

By the time we agreed to meet up in person, I already had an excellent first impression of him. It was like I’d known him forever. We had been talking for a week and a half and had built such a killer rapport that we actually decided to meet up after I got off work at 2 a.m. 

Now, when it comes to texting before a first date, your intention should always be to meet up in person. Don’t get so attached to the witty back-and-forth that you fail to ask her out in a direct way. I don’t have to tell you that most high-quality women, especially on dating apps, have many options at a time and can easily drop a conversation at any time. So always be sure to ask questions about her interests and be ready to craft an irresistible TDL (time, date location) so you can set up a real date.

That said, you don’t have to be all business about it. Use your improv skills and keep her laughing as you fish for information to propose the perfect TDL. You might even flirt a little. That way, she’ll have a sense of your personality and will feel more comfortable agreeing to go out with you.

Be Willing to Take Risks

At the beginning of our date, I picked Jake up outside a bar and we went to buy beer with the remaining five minutes the liquor store would be open. I never used to bring men over to my apartment when I was single. Given the hour and the unfortunate fact that he was still living with his folks, we had nowhere to hang out. The fact that he lived with his folks was a buzzkill- but I already knew I wasn’t going to sleep with him. Plus, it peaked my interest that he was so goddamn cocky. 

Per his recommendation, and a fun one at that, we ended up sneaking onto a soccer field and drinking beers right in the middle of the astroturf. Every time a cop car rolled by, we’d lay back and try our best to hide. 

It was a strange date, for sure — but that wasn’t even the strangest part. Nope, things were about to get real weird.

At one point, he suddenly stripped down — I’m talking BUTT-NAKED — and proceeded to sprint around the soccer field. I’d only known him for an hour and I’d had a full view of his man-ness. What a nut! I laughed like a hyena throughout the entire date.

Personally, I would always rather a guy push the limits then play it too safe.

Jake took a calculated risk — and for the time being, it paid off.

Obviously, you don’t want to make her feel nervous or uneasy with you. Still, don’t be afraid to do or say something unexpected if it fits your personality and the mood of the date. After all, if you like her, this is when you want to capture her attention.

Channel Your Inner “Alpha Male”

One thing I loved about Jake was how alpha-male he was.

He kept trying to make moves on me as I pushed him away. He didn’t let this deter him and finally, we snuck into the bathroom by the soccer field and made out.



It was hot. Well… the persistence was hot but not the actual mack skills. It’s interesting how talent plays a relatively small role in chemistry. Often, men with poor sack-and-mack capabilities stay on my mind longer than those that are good in bed but lack assertiveness.

Needless to say, I wasn’t super into it, mainly because he was so young. But I went with it and pretended he was George Clooney. 

If you want to take a page out of Jake’s playbook, think about ways you can be persistent without being annoying or scary. For example, if she says no to something, be respectful and listen. Most importantly, don’t complain or act clingy in any way! Remember, it’s about confidence, so just ask for what you want upfront… but always with the attitude that you’re willing to walk. Nobody wants a guy who seems desperate to hook up.

Show a Little Dominance

Take it from me:

Dominance, when done right, is sexy.

I ended up driving Jake home a bit later and we made out more in the car. He pulled me over to a sitting position on top of him, which was hot because it was so dominant and forceful but still sweet and sexy. I didn’t sleep with him and I think it kinda made him nuts. Not a bad way to spend a Saturday morning.

Remember, there are ways to use your physicality to ignite sexual tension on a date and make a woman desire you. Even if you’re not at the point of making out, don’t be afraid to touch her casually while you’re out together. This can be simply putting a hand on her back and she walks through a door in front of you, or brushing a crumb off her face. Believe me, even a subtle touch can do wonders in creating a dominant-yet-sexy vibe.

How to Make a Woman Desire You: Wrap-up

While I didn’t end up with Jake, he was my best date up to that point and will probably live in infamy as the crazy, 24-year old streaker with the ridiculously huge man-shlong. Big fun. Big laughs. Big…. hands. 😉

The whole point of this story is to show how to make a woman desire you by showing her signs of your inner confidence. In fact, according to Men’s Health Australia, confidence is one of the top five personality traits women desire in men.

Once a woman gets a sense of your confidence, you’ll convince her that you’re the kind of guy she secretly wants — one who will take charge and make her feel safe. It’s an evolutionary desire that women won’t always admit to out loud, but that many of us still act on. 

Your shows of confidence will also bring out her feminine energy, which will perfectly balance your masculine energy. When a woman leans into her feminine energy and a man is fully in his masculine, it creates an indescribable sexual tension. Creating this sexual tension will definitely push things forward.

You might think this sounds like it’s easier said than done. And to be honest, if this isn’t your natural personality, it’ll take some time. You’ll need to invest in new ways of doing things and develop new attitudes about yourself. Change isn’t instant, but it can be done. 



That said, it’s much easier with a coach. Many of my clients don’t have the natural confidence you’d expect from a guy who consistently gets dates, yet after we work together, I turn them into uber-successful MegaDaters. Once you dedicate enough time to undo your old habits and mindset, I promise you’ll have your choice when it comes to beautiful women.

Book a Zoom new client coaching session with me today to get started. We can review your dating situation, identify any immediate action steps to get things going in the right direction, and determine if my 3-month Signature Program is right for you.

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