On Stepping Outside of Your Comfort Zone

"What's something interesting going on in your life?"

Those are the exact words I used to open conversations with at least 2 dozen women over the past 2 nights of Memorial Day Weekend. My roommate TJ was out of town, so I had to fly solo.

It doesn't sound like a particularly good pickup line, but I chose it for a reason: if a woman can't provide a decent answer to that question, she's not worth my time. I like to think of dating like a sales funnel: I have to prospect correctly so that I find qualified candi(dates). Conversely, a woman who's a bit more intelligent can play logic games around the question. That's always a blast, and is usually a good competence trigger.

To win at the pickup game, you have to play on your own terms. If you play on her terms, you're destined for failure. Women have far more practice at rejecting you than you do at succeeding with women. That question is a phenomenal opening filter. You have to dictate the terms of the conversation, not her.

The first time I tried the line, I most certainly failed. I felt a very awkward as I articulated it, and I'm sure she picked up on my lack of confidence. I was toast. But I persisted. I repeated the exact same line with more women, and my confidence grew. By the 4th set of women, I was on fire. Women aren't used to that kind of a question to open the conversation; it takes them off guard and brings them into my world so I can play the game on my terms. I scored six phone numbers in two nights, and all six responded to followup text messages within 24 hours.

So what's the moral of the story? Step out of your comfort zone. Do something crazy. You won't learn anything by doing the same thing that you've been doing. Try something different. If you're unhappy with any aspect of your life, change it up. You'll be surprised by the results.

Now just imagine hitting on women while wearing Google Glass. I'm not going to record conversations or do anything inappropriate; I'm just excited to hear women's responses because I'm wearing Glass. I'm going to have the time of my life.