How To Pursue Her


Pursuing. This has to be the toughest part about being a guy. Are you trying too little, or too much? Are you revealing too much about yourself up front, or not enough?

In college, there was this girl I thought was “my everything.” There were good vibes happening, and she agreed to go on a date. I told her I was taking her on an island date. This was our first date and I might’ve been too excited. The planning was meticulous. I got a picnic basket, plastic cups that looked like wine glasses, artisan cheeses, meats, sparkling wine (actually grape juice), a glow-in-the-dark stick for candle lighting, and a blanket. We pulled into a parking lot much to her confusion. I led her across the street into the intersection “island,” and we set up camp for a good 10 minutes before a cop told us we had to leave. I never heard from her again. Here’s a good case of pursuing too much.

Do you overcompensate, or are you too distant? How to pursue her? There are three parts to pursuing her that require some consideration: how to approach her, your dating expectations, and how to discern between the green light rejection and the deadly rejection.

The Approach

How you initially approach her is the “make it or break it” in the pursuit. There are generally three approaches guys take: the cocky & funny approach, the needy approach, and the natural approach.

Is your goal to be a pick-up artist? For the guy who goes with the cocky & funny approach, you might experience some short-term success. There are some girls who love cocky guys. Probably not the kind of girl you want to take home, but I get it, you’re not even thinking beyond tonight. So you go out and you use negging, pick-up lines, and all sorts of techniques you’ve practiced over and over. You’re really hoping being funny will overcompensate for the cockiness that will turn many girls away. This approach is an act that won’t work with confident women (they’ll see right through it). Either way, you’re putting on an act, and once the act is created and works, your dating life will become a revolving door of empty relationships. Just don’t expect anything long-term.

Then there’s the needy approach. Here, guys spot a girl, and decide she’s a divine goddess who will meet his every need. This guy needs female validation. He’ll go overboard hoping to win her over. He may buy her drinks, send her daily flowers, wash her car, paint her house, become her personal assistant, talk to her about her previous relationships, set up her dates with other guys, etc. Ultimately he comes across too nice, desperate and insecure. Believe it or not, this approach works with some women too. However, these needy men become angry indentured servants who spend the rest of their lives abiding to a nagging wife.

The only approach with good, long-lasting effects is the natural approach. In the natural approach, the guy walks into a situation with zero expectations. He’s there to have a good time. He has confidence within and doesn’t need external validation. When he sees the beautiful girl across the room, he sets her external beauty aside for a moment, and decides he’s going to make a new friend. His objective is to get to know her as a person, not to have a one-night stand, nor to decide she’s his wife. If there’s chemistry, great, but if there’s none, the night isn’t ruined.

Your dating expectations

The natural approach also works because this guy isn’t going to give up his values or integrity in trying to get a girl. He knows himself, knows exactly what he wants, and doesn’t compromise everything just because she’s a potential trophy wife. On the contrary, he’s looking for character traits that are good beyond one night. He might even have a list (The Girlfriend List, The Wife List).

His dating expectations are a strength that do not require a cocky or desperate act.

And yet, even after our hero has crossed the treacherous terrain, and survived the Sirens, he may end up at The Gate of Confusion. Read on: When To Stop Pursuing Her: The Green Light Excuse or The Deadly Rejection.


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9 Responses to How To Pursue Her

  1. CHUDI DANIEL November 12, 2014 at 10:04 am #

    Thanks for this, I think it’s really helpful. I have one small question regarding the Natural Approach and going in with “zero expectations”. I’m attracted to a lady, I’ve set her personal beauty aside and I’m so much more interested in having her as a friend and getting to know her as a person (I really am). Doesn’t this already form an expectation (albeit noble)? I dunno. I just think it’s difficult going in with “zero expectations”, because even though I’m fully open to the possibility that things may or may not work out as I ultimately hope (to build a great friendship that can possibly bud and grow to something more), it’s my expectation that has me walking up to her in the first instance. Sure there’ll be other ladies I just walk up to and don’t expect anything from really, but If you’re attracted to a lady (like you were to Kristen), it’s really hard to have “zero expectations”. I hope you understand my “confusion”?

  2. MoricErianna December 22, 2014 at 12:26 am #

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  3. Remy Sheppard January 7, 2015 at 2:47 pm #

    For the guy who goes with the cocky & funny approach, you might experience some short-term success. There are some girls who love cocky guys. Probably not the kind of girl you want to take home, but I get it, you’re not even thinking beyond tonight.

    Thank you for insulting both me and my wife. Its good to know that she isn’t the type of girl I’d want to take home.

    You literally described exactly what I did to meet her, and then called her trashy and easy.

    • Kris Wolfe January 7, 2015 at 6:37 pm #

      You’re a former pick-up artist who used a pick-up artist technique to meet your wife? Please email me. I’d like to hear more.


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