How To More Confidently Approach Women, Create Conversations, And Get Dates Now

It’s very common, when dealing with the topic of dating and relationships, to hear people say that you should try to “play it cool.” What they mean by this is that you should ignore the person you’re attracted to so that you don’t seem too eager (desperate).

While that may work for some people, many of us end up using the “play it cool” tactic as an excuse to hang back and wait for the other person to come to us. We play it so “cool” that we end up standing by ourselves in a corner all night and missing out on opportunities to connect with someone who might be perfect for us. This is a big mistake.

Today, we’re going to dive into the topic of confidence in dating. More specifically, we’re going to discuss how to not play it cool—how to show up boldly and go after the things you want.

This is an area that so many of my clients find puzzling. I struggled with this idea for a long time as well, and it’s no surprise because we’ve been trained to think that showing enthusiasm or excitement about something us uncool.

Let’s say you’re out and about, and you spot an acquaintance you’ve always wanted to ask out on a date. What do you do? Maybe you get into her line of sight hoping that she’ll see you and initiate a conversation. After all, you don’t want to seem desperate, right? If she’s not too busy and she’s into you, she’ll say hi.

If this is the approach you’d like to take, then you are not alone . . . I used to think this was a pretty smart move, myself. The problem: it’s not doing very much to help your cause.

Let’s change the situation: you’re out and about, and you see an acquaintance with whom you always enjoy pretty good conversations at social events. What do you do? You probably walk right up to the person, get his or her attention and say, “Hey, what’s up!” and proceed to have a quick but delightful conversation.

What’s wrong with this picture? You avoid communication with the person who might end up being the girl of your dreams, yet you confidently insert yourself into a comfortable social interaction with someone who’s not too likely to bring you even one step closer to lifelong happiness.

That’s not playing it cool—it’s madness.

The truth is that it’s not actually madness either . . . it’s fear. We’re scared. We’re scared of putting ourselves out there; of being rejected; of finding out we’re not good enough for that person.

I have clients who won’t even look at a woman for fear that she’ll think he’s creepy. First of all, you’re only creepy if you’re lurking in a corner gape-jawed with drool dripping onto the floor. Assuming this is not the case, it is possible for you to notice a beautiful person and meet her gaze without coming across like a lecher.

The main question we have to ask ourselves in that moment of meeting someone else’s gaze is why we feel compelled to quickly look away as though we’ve been caught in a malicious act. When you think about it, you realize: it takes two to tango. Yes, you looked at her; but she looked at you too . . . didn’t she?

Looking away guiltily is nowhere near as creepy as leering at someone from a dark alley, but it doesn’t exactly make someone want to start up a conversation either. If you happen to meet eyes with an attractive woman, the trick is to stay calm and offer a kind smile. Most women even find it endearing to acknowledge the moment with a little wave that says, “Hey, sorry I blanked out on your face for a minute.”

This idea that we’re somehow going to come across as desperate just because we’ve made eye contact or initiated a conversation is simply a myth.

Truthfully, we have to boldly show up and take action if we ever hope to get what we want out of life. We have to get her attention; we have to make the first move. If nothing else, it lets her know that we’re interested in her! In fact, it can excite a woman to be approached by an admirer, especially if he’s confident and unapologetic about it. If she’s not into it, then you both go about your day and you probably never see each other again . . . what could be simpler?

Now, by my calculations, playing it cool results in about a .03% success rate (and I should know; I tried this move for almost eight years). While it may work out well for professional athletes and characters in romantic comedies, it’s probably best for those of us living in the real world to stick with methods that produce better outcomes.

So be bold! Step up and make the first move!

If the very idea of making the first move makes you want to crawl into a hole and die, check out my podcast, “Shrink for the Shy Guy” at Better yet, go to and join my full dating program, which will help you break through your fear and give you all of the tools you need to get to the next level and really handle your dating life once and for all.

You can also share, like, subscribe, or check out other episodes of this show by clicking the available links around the video. Let me know about your hold ups with playing it cool and how you overcame them. We learn by absorbing the knowledge of others, so please keep the communication going, and share your experiences with one another.

Until we speak again, may you have the courage to be who you are and to know on a deep level that you’re awesome.