4 Women on Street

Now that I’ve started a new chapter in my life I want to start putting this into practice by initiating starting conversations with women that I see while doing every day things. I wrote about some of these already here and here but I wanted to step it up a notch and see if I could go into an every day situation and start up a conversation with a woman I was interested in.

It just so happened that I had a few errands to run today and I thought, hey, why don’t I practice this skill while I’m out. I went to a computer supply store to buy some DVDs and noticed the cashier was a cute girl – way too young for me so I wasn’t about to ask her out, but I wanted to practice some harmless flirting. She didn’t respond that well and was very business-like. I thought it was too bad because it would have made her day more enjoyable. I didn’t take it personally but at the same time, I didn’t really take any chances. I just said “hello” and “how are you” in a nice way and tried to be friendly but I didn’t try and joke around with her to get her out of her serious state.

Then I went to a grocery store. I didn’t realize how many opportunities there are all around me in an every day setting like a grocery store. There were at least 2 attractive women that I could have approached today from spending about half an hour there. I let these 2 opportunities slip through my fingers. The first one was when this gorgeous woman strolled right by me close to the entrance of the supermarket. I was strolling around with my cart checking out the groceries and suddenly there she was walking by right in front of me. I just kind of looked at her as she walked by and didn’t have the guts to just stop her and say hi. The second opportunity was when I was waiting in line at the deli counter. I turn around and see this really cute woman waiting in line about 10 feet behind me. We exchanged a glance but I didn’t follow it up with anything. I just smiled (which I guess is a good start) and then turned my glance back to the guy behind the deli counter that was filling my order. After about a minute I turned around again but she was gone.

Despite not taking action with those 2 women, I ended up talking to many people along the way and had fun doing it. I talked and joked with the guy in the fish department, I briefly chatted with this cute woman who was shopping with a baby, I talked with the cashier as she rang my order through (I made a point of going to a checkout with a cute girl working there so I’d have another opportunity to practice), I talked with the cashier at the computer supply store.

The woman with the baby was an interesting case because we exchanged smiles first as we passed each other and I felt like an idiot for not following up and starting to talk with her. Then she came back my way and I noticed that she had a baby with her in her shopping cart so I knew I wasn’t going to be asking for her number. Nevertheless, I still managed to briefly talk with her, which made me feel better for not completely missing the opportunity to practice being more social.

Overall, I feel it was a good start. Sure, I didn’t end up talking to the 2 women I was really interested in but I feel like I’m on my way there. Also, I just had more fun shopping for groceries than I usually do. I’m also appreciating the fact that talking to attractive women is just a subset of talking to more people in general. I’m noticing that I’m becoming more social as a person, which I like. I don’t want to be a guy who only talks with women he’s interested in. I want to be more social in general because that will help me to better interact with women that I meet while I’m out.

In the future, I’d like to set a goal like “I’m going to talk to 1 woman” today while I’m out running errands. I’m not ready to commit to that yet but it’s something I aspire to.

So what did I learn today? Right now, it’s not easy for me to start talking to a woman I’m attracted to in a public setting. At the same time, I found it easy to start talking to women I’m not attracted to and men. I also found I had more fun doing my errands than I normally do and I ended up talking to a lot of people!