In my ongoing quest to get better at talking to women in public, I decided to give myself a concrete challenge to keep me focused on my goal. I’m going to describe the rules and motivations of this challenge I’m setting out for myself.

Rules for The Approaching Women Challenge

  • Approach a total of 50 women before June 18, 2007. The pick up approaches that I’ve already done count towards the goal. That means I’m up to 21 already. Interestingly enough, I’d actually be at a higher number if I set these rules up previously – like my very first post where I picked up a woman on the subway. So this means I will approach 29 more women before the due date.
  • I’ve given a close friend of mine $50. If I reach my goal by my due date, he gives me back the money and if I don’t, he keeps it. Simple as that. I wanted something more concrete to keep me focused on my goal. Even though I might know in my head why I’m doing all of this (so I can improve my life and so forth) there’s nothing like the potential loss of money to give me that extra push and prevent me from making excuses.
  • Talk to each woman for at least one minute – that way I can’t count saying “Hi” or asking, “What’s the time?” as an approach. At the same time I don’t want to have the pressure of asking each woman out that I approach – I’ve already made that insight before and it’s served me well. So after one minute of talking, I can decide if I should continue talking to her or move on. Following my previous insight, this means I do not have to ask out every woman I talk to.
  • The outcome is not important – it doesn’t matter if she says yes, no, completely ignores me, gives me a fake number or I decide not to ask her out. The main point is to make it no big deal to approach women I’m interested in. Period. In public, at parties, wherever.
  • Talking to a group of women counts as one approach. So if I end up talking to a group of three women at a bookstore, it counts as one approach.
  • If the woman cuts off the conversation before one minute, it still counts as an approach. So in the (highly unlikely 😉 ) event where she flat out says, “Get lost!” or “I can’t talk right now.” I should still get credit for approaching her.
  • Talking to female staff (waitresses, store clerks, etc.) only counts as a pick up approach if I ask them out. It’s too easy to talk to women that are naturally more open to talking (e.g. when I’m a potential customer at a store). So if I happen to like a waitress and decide to ask her out, then it counts as an approach.
  • Talking to women at social events (parties, networking meetings) doesn’t count as a pick up approach, unless I ask her out. That way I can’t count talking to a slew of women at a party as approaches.
  • The woman must be reasonably attractive and close to my age – that way I can’t count talking with little old ladies as an approach. She doesn’t have to be hot but someone I could conceivably go out with.
  • If I start dating someone exclusively before I reach my goal, then I get the money back. That way, I won’t feel pressured to continue talking to women after I start seriously dating someone. (Who knows, I might end up amending this rule since I don’t have to ask women out, just talk to them.)

Improving my ability to meet women is more important than dating or even having sex right now – besides not being attracted to Angela, I also felt that continuing being friends with benefits with her was going for the easy sex and not improving my ability to meet more women. It was a short-term win but a long-term loss. Don’t get me wrong – if I end up dating and sleeping with women that I’m pursuing right now, I’m not going to be a dumb ass and say no. But I want to make it clear that that’s not my goal – it’s not to sleep with more women or even go out with more women. It’s really about improving my ability to meet more women. I know the dating and sex will naturally follow if I improve this one area.

Ultimately, though, it’s about meeting the one woman that I can settle down with.

So wish me luck and let me know what you guys think – good or bad. I’d love to hear from you.