7 Keys to Confidently Approaching and Meeting Her

7026426983_a0e6ab5f82_zAt the end of the day, the more often you express yourself and approach women that catch your interest, the more confident you’ll feel, and the easier it will be.

Suddenly, you see her. She looks perfect! You want to go over and talk to her. You’re a good guy, and you want to see if there’s a mutual connection between the two of you.

Approaching her with confidence is essential in getting to know her better.

But how? What do you say? Do you just waltz up and tell her you’re interested? Or do you start more conservatively? As a dating coach and a gent who’s personally met many women in this very way, I can confidently say I’ve learned a ton regarding what works, and what doesn’t.

I’ve learned that there’s no such thing as a “guaranteed to work pickup line.” However, there are many ways to aid you in making a great first impression. Right now, I want to share with you the #1 secret for kicking things off in the right direction. It’s approaching her with confidence.

Approaching her with confidence is essential in getting to know her better. Women love when a great guy gives her the gift of approaching her with confidence. The question then becomes: how do you generate that winning feeling inside just before you go? Below are my seven keys. (The first four are to support you before you talk to her, the last three will serve you for once you do).


Key #1: Come from a place of giving, not from a place of taking. When you see yourself as giving a fun opportunity for two people to meet, you immediately shift from a place of scarcity to one of abundance. Most guys feel like approaching her is equivalent to begging for money. Why? As the guy, you’re not taking anything! You’re giving. Specifically, you’re giving her a chance to experience something spontaneous, something exciting, something new. You’re creating an experience. Never forget this.

Key #2: Remind yourself that most guys never approach the woman they desire. With this in mind, pat yourself on the back for having the confidence to put yourself out there. Taking a moment to acknowledge your courage, before you approach her, makes you feel more confident. This is huge. You see, the human brain responds to fear and reward. Most guys associate approaching her with fear and pain. But not you. Instead, by patting yourself on the back, you’re associating approaching her with pleasure, with reward. This boosts confidence.

Key #3: Accept that she may or may not be interested. Acknowledging that she may say, “no thanks” before you introduce yourself actually fuels confidence. Why? Because you’ve accepted all outcomes (including the worst) ahead of time. Essentially, you’ve faced the fear of rejection head on. As the saying goes, “Plan for the worst, expect the best.” When you do accept all outcomes ahead of time, you free yourself to approach her with a focus on the opportunity at hand. Consequently, you’ll exude more confidence this way.

Key #4: Remember there are plenty of fish in the sea. The truth about approaching her is that it isn’t that big of a deal. Of course, it will feel like a monumental feat at first! But with time, you’ll see that it’s just a unique interaction between two people. And here’s the truth: while there’s a small chance that she’s THE ONE, there’s a much better chance that your future wifey is yet to present herself to you. In knowing this, you alleviate pressure to perform. Accordingly, you’ll feel more confident.

Key #5: Approach her within three seconds of seeing her. By acting swiftly, you’ll stay out of your head and remain in the present moment. This is ideal. Most guys overanalyze. But not you, you’re a man of action. You make your move. You trust that the words will come. This is confidence in action. So you know, the natural words that come out will be more attractive than almost any “pickup line.” What naturally flows from your mouth without preconceived consideration is authentic, whereas premeditated pickup lines are cheesy and fake. She can tell the difference. Likewise, speaking authentically fuels self-trust and confidence, whereas relying on pickup lines mitigates it.

Key #6: Be willing to share about yourself before asking all about her. As the man, you’re expected to lead. And while you just led by striking up a conversation, immediately bombarding her with questions puts her on the hot seat, and can make her feel uncomfortable. After ensuring she has a moment to talk, share a bit about yourself. Tell her a story, talk about your passion, your hobbies. Then, give her the opportunity to reciprocate. This takes pressure off of her to immediately open up to a stranger. It also allows her to get a sense of what a cool guy you are. Knowing this little secret makes for a better conversation, and thus, increases confidence.

Key #7: Never judge yourself negatively after you approach her. The natural tendency is to beat ourselves up when things don’t go our way. Instead, take a step back and consider the interaction objectively. If there was something awkward or weird you did, take note of it and learn the lesson. But then, pat yourself on the back for having the courage to talk to her, and move on. Remember, nobody bats a thousand. In any discipline or field, high achievers fail regularly. What separates them from the pack is they always learn the lessons from the specific event, and then, they reground themselves in their self worth and moved on. Do the same, and you’ll feel more and more confident every time you put yourself out there.


At the end of the day, the more often you express yourself and approach women that catch your interest, the more confident you’ll feel, and the easier it will be. It becomes an upward spiral! Use these seven secrets to jumpstart your dating life!

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Photo: Flickr/ Ed Yourdon

About Jason Rogers

Jason Rogers is a dating and personal development coach for men, creator of peakunderpressure.com, and the Founder of PEAK Inc., who's mission is to help men improve their social and dating lives. As an awkward, shy, and rather unhappy person growing up, Jason discovered personal development and used it to improve his life. Now, he is passionate about using personal development strategies to create powerful and lasting change for his clients. Contact him at jason@peakunderpressure.com.


  1. Edward Fotion says:

    Thanks Jason!
    I was really able to see that you are filling your own tank
    and the tank of your clients and prospects,
    instead of draining the tank of those that you meet.
    I love the fact that you are working so hard at bettering
    yourself and helping others become better and more effective!

    Edward Fotion

  2. John Anderson says:

    One of the things I’ve heard is smile, not necessarily at her, but smile.


    once I was looking in the direction of a woman and her friends, smiling because of a pleasant memory. Abouty a minute later, one of the women turns to her friends and I could here her complain is he just going to sit there or is he going to do something.

    Pleasant people attract others. We all want to be around those who are having a good time. That’s why I tell guys to go out with the goal of having a good time rather than trying to get a date.

    • Totally agree. Good mojo goes a long way in socializing and dating. A guy could “break all the rules,” but if he’s authentically having fun and smiling, he’s going to be just fine 🙂

      Thanks for sharing!


  3. Thank you Jac!

  4. Developing confidence is key (for both sexes). No matter how attractive a person is, there are often insecurities. These are great pointers Jason and can apply to both sexes. Nice article!

  5. Jason
    “Approach her within three seconds of seeing her”.

    In many situations this is a not smart and actually acting desperate .
    Women do see and know what is happening around them Jason.
    Imagine the man visit his church. Or goes to a huge conference .
    To approach the first woman he like a lot he like within three seconds , is a stupid act in settings with lots of people .
    I hope you see why.

  6. I was painfully shy as a child but as an adult I eventually learned to interact comfortably with anyone. The key really is just practicing. Whenever you are out, talk to people. Make conversation with everyone – clerks, Uber drivers, old ladies. Just be friendly. Chat with coworkers in the breakroom who you’ve never talked to before. Chat with middle aged women in line at the grocery store. You will learn a lot from this… how to tell when someone wants to chat and when they don’t, what’s the best small talk, how to wrap up a conversation. It’s low pressure because you aren’t trying to impress anyone. You also realize that people vary greatly in their skills at conversation – if an interaction with a woman goes awkwardly, it could be that she’s awkward, not that you did or said anything wrong. In my younger years, when I was quite shy, I totally wrecked many conversations with men because Inwas shy and awkward and responded badly to their overtures. They probably went away kicking themselves when it was actually my fault. So many of these types of dating articles assume that women (particularly attractive women) always have their sh!t totally together and are extremely highly skilled socially and always know exactly what they want. That is completely wrong. They may be as confused and anxious as you are, or more so.

    • Becca – absolutely agree with chatting with everyone. Coworkers, baristas, clerks, … everyone!

      Thank you for sharing.

      Cheers, Jason

    • FlyingKal says:

      My experience is rather the opposite.
      As a kid I felt I could engage with almost anyone (although I mostly had the respect to know when it was inappropriate)
      But growing into my teens, I started to get increasingly rejected in trying to make ordinary small talk. So I started to question myself, what was wrong with me, at the same time I saw my friends and other people around me rather easily increasing their conversation abilities.

      I’ve been turned down so many times, somehow wrecked so many conversations before they even started, that today I mostly feel that I rather not engage in conversation at all, if I don’t have to.

  7. Brilliant, Anthony

    Done it. Still do it even married, but with no intent to pick up…just no fear of striking a conversation with women.

    I’ve been in a doughnut shop and seen a younger women (dressed and with other people for a bike ride). She was pondering, looking for something non-fattening…or something. She looked at me as said, “you can go, I’m still deciding”. I told her I’d be quick, I just want the most fattening, disgusting, gooey thing they had as I’ve lost a pound or two and need to pack that back on.

    She laughed, and the conversation was on. I almost felt as though she was going to ask me out as we walked out together, still chatting up a storm, exchanging quips…which, I, of course, would decline.

    Done it in a Home Deport. Two women waiting for the yard guy, and waiting, and waiting as the line went down and I went through. I asked them were they are parked, tossed the few pieces of lumber on my shoulder and told them, Lets go. I have it.

    They both said that I don’t have to do that. My reply was, “yeah I do. Busy day today and I need to get my gentlemanly task out of the way early.” They laughed, and boom, conversation on with not one, but two.

    For any guy reading this, it’s a process. It does not even have to be sexual, or dating focused, but just general conversation. Humor is a tool, a great one. Helping with something, as Anthony stated, is another. Doing so in a non-creepy, but comfortable way is the greatest of all.

    There are so many ways to strike conversation, and a guy will learn them, learn what works, what causes you to crash and burn (which we’ve all done – some, ahem, more then others).

    Thick skin, a modicum of courage, and practice, practice, practice, and it will become almost natural.

  8. you don’t lose, you learn. The only way to win is by learning. If you have the shot, take it.

    I often tell guys to move in baby steps. One does not have to jump off of a bridge, but simply push their comfort zone a little at a time. Take risks, even small ones as each will build confidence ontop of confidence.

    Good example is weight lifting. One does not through 3- 45s on each end of the bar and try to push that on the first day. You toss a 25 on each end, work that, let the muscle rebuild, then push a little more then next time out, building as you go.

    Same with confidence. Numbers game. Plenty of fish, but you catch nothing if you don’t cast out.

    Good read, Jason.

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