I recently participated in what I call the “7-Day Challenge” with another girl. The 7-Day Challenge involves meeting one new member of the opposite sex every day for an entire week. It’s meant to be so simple that it would be hard to fail and would empower each of us to stretch and improve our social skills. It was not about getting a phone number every day, but simply getting used to the everyday act of approaching a complete stranger and engaging them in a conversation, a lifelong skill that goes far beyond dating. I kept track of each experience and had an epiphony by the end of the experience. I’ll start off by relating the first day
Here are 5 Tips I learned
Monday: I figured the best time to talk to a woman would be after work and while doing things I was already doing. I stopped off at a local coffee shop that makes a good cappuccino on Venice called “Venice Grind” They have local artworks on the wall, a friendly bartender named Eric with a big smile, free wi-fi and a tasty banana cake. As I walked in, I saw a girl typing away at her laptop near the front with an open table next to her. The evening sun was harshly shining directly on the open table but that was not enough to deter free from snagging a seat. I put my backpack below the table, ordered my coffee and sat down to read the newspaper.
Tip 1: Small talk is a great starting point
After reading and enjoying my coffee, I had to use the restroom. I turned to the girl, a redhead with bright eyes and asked, “Would you watch my backpack while I go to the bathroom?”
“Sure,” she said, barely looking up from her laptop screen.
“Thanks,” I replied.
Tip 2: Crack jokes and be light-hearted
I returned and on my walk back took a look at my backpack and grinned.
“You did a great job guading my stuff,” I said and playfully added. “No one stole anything. Excellent job.”
She smiled back and I could tell she was amused.
This moment reflects how easy it is to approach any situation and turn it into something playful. Use your surroundings to get a little bit of conversation going that has a light-hearted tone. Here I exaggerated the simple act of watching one’s stuff in a coffee shop, which everyone has done at one point in their lives.
Tip 3: Continue the conversation by commenting on a simple observation.
Quick question to the reader: Based on everything I’ve already described, what would be an easy way to continue the conversation with this girl?
For me, the most obvious one is: What was she working on at the coffee shop? Maybe she’s a student studying for an exam. Maybe she’s checking her facebook status to see how many “Likes” her last post got. Maybe she’s writing her first book on dating, like me.
Side note: The book is called “Dating on a Dime: 20 Inexpensive Dates in
” and I have written 12 out of 20 chapters so far. I’ve been taking my time writing it and filling it with insights, anecdotes, humor and lots of good tips. It’ll probably be done in the next month or two. Los Angeles
“What are you working on?” I asked.
“I’m looking up costume ideas for a short,” she said.
And with that simple question there were now two fun conversation threads to explore:
- Costumes, which tells me she’s probably into fashion and helping other people choose outfits for whatever reason. In this case her reason was for a…
- Short Film, which is easy to talk about for me because I’ve directed a few short films and I’m a huge cinephile.
Tip 4: Closing the deal, sometimes the opportunity isn’t right
As we talked, a guy and a girl arrived to join her. They were all friends and she shifted her attention to them and so I went back to working. I planned to stay for at least an hour more, and I noticed through the corner of my eye that after 10 minutes, they all got up and left together. As she stood up to leave, we bid each other farewell and that it was good to meet each other.
Because there were two friends there, I didn’t have the desire to ask for her number on the spot. It didn’t feel right. Looking back, I think I could have done it in a casual way, and in the future I would have asked her out to get a coffee another day as it’s better to go after what you want, even if it doesn’t work out.
Tip 5: The most important part is how you view the interaction, no matter the outcome.
I could have seen this as a failure on my part, but instead I saw it as a part of my growth and learning. I am proud of myself for having the courage to talk to a complete stranger at a coffee shop. The situation put me in a good mood and later when I went to the gym, I ended up talking to two attractive women in a similarly casual and flirty way.
I encourage everyone, man or woman, to go out and start approaching people of the opposite sex. You have nothing to lose and everything to gain and at the very least you will improve your social skills…which will come in handy down the road, as I’ll share later.