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How to Be Mysterious When Dating a Woman You Like

How to Be Mysterious When Dating a Woman You Like

How to Be Mysterious When Dating a Woman You Like

The one dating skill I wish every guy out there would learn is how to be mysterious with women while dating. It’s the one quality that men don’t cultivate enough — but desperately need to.

Being mysterious can increase your dating success tenfold. Why? Think about human nature. People tend to “want what they can’t have.”

Dating is NO DIFFERENT. If a woman feels like she knows everything about you in two seconds, she’ll make a snap judgment on you and move on before you have a chance to even think about a second date. Being mysterious, on the other hand, will pique her curiosity. She’ll have to continue seeing you to discover what you’re all about. And the more time she invests, the better chance you have of winning her over.



Of course, this is the best-case scenario. Instead, what do most men do instead? They’ll text her incessantly, respond too quickly, spend WAY too much time with her on the first date, get over-anxious instead of going with the flow, and develop an almost incurable case of one-itis.

Don’t be one of these guys. Read on to find out how to be mysterious when dating a woman so you can reach your dating goals faster.

How to Be Mysterious With Women

Use the Law of Supply and Demand

For all you non-economics majors out there, it’s important that we first discuss what the law of supply and demand is: When you have a valuable commodity that’s not readily available, the demand for it goes up. But as that commodity becomes more available, the demand goes down.

Think of yourself as the “commodity,” and the woman as the buyer. To make her desire you, you need to “raise the demand.” How do you do this? Make yourself less available, so you position yourself as a rare commodity.

This means you must control the amount of time you’re available to see her. The best way to do this is to employ a strategy I call MegaDating. The rules of MegaDating are simple: Instead of focusing on one woman at a time, reach out to several women and date as many as you can at once, so your social calendar is always full. It may sound easier said than done, but I assure you it’s not.

Once you become active on several dating sites or apps (I recommend no less than five), use effective IRL techniques to meet women, combat nervousness, clean up your look, and communicate with confidence, you will create a steady rotation of dates.

A lot of these may be first and second dates only — but the point of this strategy is not to find the woman of your dreams right away. It’s to create momentum. This is where you get into a groove of dating regularly. Sometimes, you might even make plans with more than one woman in a day (yes, it’s possible!). Dating to that degree (hey, it’s called MegaDating for a reason) will not only make things a lot more fun, but it’ll shift your energy in ways you might not expect. Once that momentum hits a critical point, your confidence level will increase, and women will be able to feel it.

But the best part is, you won’t always be available when a woman wants to see you. That leads to anticipation on the woman’s part, which becomes a powerful force in her mind. Suddenly, you’ve created the “demand” you’re looking for. She’ll wonder where you’re going when you’re too busy to see her, and the mystery will keep her interested.

Avoid Texting Between Dates

Do not message her in between dates. If you want to know how to be mysterious with women, that’s an important thing to remember.



Many men assume that the way to keep a woman interested is to “stay on her radar.” They’ll spend the entire week between dates sending her silly emojis, asking how her day’s going, and basically checking in for no reason, so they won’t be “forgotten.” Wrong, wrong, wrong.

Don’t let her get to know you over text. Instead, use the time between dates to build mystery and allow her to fantasize about you. What she imagines you to be will be much more powerful than any clever text you could come up with.

Only text her to arrange or confirm the next date. Ideally, you would have set up the second date by the time you were done with the first one. If you did this, congrats — you’re one step ahead. Only text her to confirm that date; otherwise, keep things mysterious and save any further conversation for your next outing.

If you don’t have another date set up, then your only communication should be If you’re lay down a solid TDL (time, date, location) for a compelling date idea. You can text her or pick up the phone to ask her out. Either way, be sure to follow this formula:

  • Pick something fun or adventurous
  • Incorporate what she likes or wants to do
  • End with a time, date, and location

What’s the reason for the formula, you ask? You’re competing with other men. Wouldn’t it make sense to craft the coolest, once-in-a-lifetime dates that no woman would say no to? And doesn’t it make sense to lock it down with a date and time once she’s interested?

Whatever you do, never ask her what her schedule looks like. Just give her the TDL and overcome her objections if she can’t make a specific day or time. When a man asks, “what does your schedule look like?” it immediately shifts a woman into her masculine side by making her the leader of the TDL. Don’t do it; she doesn’t like it. Be the leader by crafting a compelling TDL that sounds like a once-in-a-lifetime opportunity. This way, she can’t say no. Women love it when men own their masculinity and lead. It’s very sexy!

Don’t Tell Her How Great Your Life Is

During my 100-date experiment, nearly all of the men I went out with tried to impress me with how much money they made. They would also tell me how awesome their job was, the type of car they drove, how epic their home was, or something else status-related. Many of these guys didn’t make it to the second date — and if they did, it was probably because they were paying for dinner.

If you go on and on about your success, then you won’t leave anything to mystery. If you didn’t tell her every last detail of your job, or what you own, then she’ll naturally wonder more about what you do, and will be more intrigued to find out.

Bragging will also make you come off as insecure. If you were confident in your dating skills, you wouldn’t talk status to try and seem important. One study published in the National Communication Association’s journal Communication Monographs even found that bragging too much can decrease people’s interest in your dating profile. Also, because so many other men make this mistake, you won’t stand out. You’ll sound like every other guy who’s tried to impress her, and she’ll likely tune you out.

Interestingly, this strategy can work particularly well if you have an introverted personality. A lot of guys hide their introverted tendencies out of a fear of not seeming “confident” — but again, bragging endlessly isn’t what confidence truly is. Don’t make the mistake of forcing yourself to get into “sales” mode when you’re out with a woman. You don’t have to put on the same mask with women that you do at your job. In fact, it won’t work. If you naturally don’t like to talk about what you’ve done or what you have, then that’s perfect. For once, go with your introverted nature a bit, and keep it toned down.



Of course, at some point, you do want her to know what a great catch you are. So the question is, how do you let her know? A good rule of thumb is SHOW don’t TELL.

Take time to slowly reveal why she should want to be a part of your life. For example, if you own a web design company and make $300,000 per year, don’t tell her this right off the bat. Just tell her you’re a web designer and that you LOVE what you do. When she finds out you’re the owner of the company and that you’re successful, she’ll appreciate you that much more for being humble.

Orchestrate the Fairytale by Not Revealing the Entire Plan

While you may have planned an epic date, you want it to unfold as if by magic. Don’t let on that you planned every detail and never let her in on all of your plans. This way, your date will seem like a fairytale and she’ll never realize you planned every step strategically.

How do you do this? When you invite her on an epic TDL, only give her the information she needs to say “yes” and meet you at the location. If you have planned an epic date where you grab a coffee a location A, then walk around the park and move to location B, and then C, she doesn’t need to know all of it. She only needs enough information to say “yes” and to meet up at the first location. You can then casually suggest the other activities/locations as the day goes on and you move around.

Let the mystery surprise and impress her. Showing her, rather than telling her, will earn her curiosity and make you very sexy and mysterious in her mind.

You Must Master the Skill of Date Planning!

To come up with a compelling date idea, look at her dating profile (if you met her online) to see what she likes. Otherwise, think back on your conversations — or if you met through a friend, ask that person what she’s really into. If she loves dogs, incorporate dogs into a date. If you can surprise her, even better. She’ll get more curious about you the more you pay attention to the details.

So you might say something like, “I know you have a pug… Did you know that Pug Nation is having their outdoor Halloween festival this Saturday and Sunday? It’s awesome… tons of people bring their pugs there, and they’re all dressed in costume. How about we take Frank on Saturday at 12?”

Of course, coming up with that one killer date idea that really resonates with her is crucial. If you need help crafting epic dates that are sure to skyrocket mystery and sexual tension, book a session with me. In my Signature program, we cover date planning, and I teach my clients how to plan the most amazing dates that none of your competition has thought of. Having a compelling date strategy that makes you look like Prince Charming is the key to differentiating yourself from the competition and winning you the girl of your dreams.

How to Be Mysterious: Wrap-Up

If you’re looking to find out how to be mysterious when dating a woman, the answer is: Less is more. This probably flies in the face of everything you’ve been taught as a man, but trust me when I say that dating is not an area where you want to be overly aggressive, needy, or transparent. Cultivating a sense of mystery will draw women to you, and it’s actually not that hard to do.

A guy who’s attractive and confident without laying all his cards out on the table automatically makes a woman wonder about him. She will “fill in the blanks” when it comes to what she doesn’t know, imagining him (i.e., YOU) to be her ideal. This keeps her motivated to keep going out with you … which gives you enough time to charm her ass off.



So next time you meet a woman you’re interested in and things seem like they’re going well, just pump your brakes a little. Play it cool, continue MegaDating, and then let her come to you. I promise you’ll get much better results.

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