Approaching women has been tough for most of my life. I've struggled with self image issues, primarily my height, for most of my life, which among other things makes it difficult for me to work up the courage to approach women. I've been in the near-vicinity of countless cute girls within the past few months. Each time, without fail, I've walked away without attempting to approach. After feeling sorry for myself for long enough, I made the decision Friday night that enough was enough.

Approach #1: I arrived at a music festival Saturday afternoon with the intent of approaching as many girls as possible and bringing home a few numbers. I attended the festival with two friends, but arrived an hour early with the intention of checking out the scene and getting some approaches in. Let me tell you my friends, I was terrified. There were gorgeous women as far as the eye could see. I walk around looking to find a girl who looks open to being approached. Naturally, I psych myself out each time and feel a bit discouraged, not helped by the fact that most of the girls here seem to have come with their boyfriends. Eventually, I walk around a bit more and see a gorgeous redhead by herself carrying a seltzer drink that I didn't recognize. I open by asking her what Seltzer brand she was carrying. It turns out that she works for the drink company and is at the festival promoting the drink. All in all, it was a surprisingly solid conversation. I asked if she was handing out samples (she wasn't) then mentioned that she should be getting the same perks that the Red Bull girls do ("Oh my god, I know right?" she responds). At this point, my friends arrives and I leave to go meet them. I totally missed a chance to ask for her number, but was feeling quite pleased with myself nonetheless. Unfortunately not much later a torrential rainstorm arrived, cancelling the remainder of the festival :(

Approach #2: I found myself taking a stroll around my neighborhood (I live in a district very popular with the brunch crowd. I really need to spend more time approaching here. Issue is that, once again, most girls seem to come here with their boyfriends). I see two Southeast Asian women chatting on a bench. After debating whether or not to approach for 2-3 minutes, I approach them and ask if they know where to find the wine store, as I had visited a wine shop in the area recently with a friend but couldn't remember its name or how to find it as I was quite drunk when I first visited. Neither of them know where the shop was and I wasn't really feeling a connection with them, so I thanked them and made my way back home.

Approach #3: This one was rough. I psych myself up in the car outside of Barnes & Noble, as I know I am likely to find approachable women in the store as I plan to grab coffee and work on my novel. I enter the store and within seconds, I find myself next to an absolutely stunning Latina. I immediately pysch myself up and have to spend time amping myself up in the next shelf over for a few minutes before making my way back over to her direction. As she is browsing the shelves, I ask her if she knows of any book clubs in the area. She replies with an awkward “No”, and I completely and utterly stumble here and mention something about not having any friends who enjoy reading. I ask if her friends like books (again, another “No” in response). I realize at this point that the game is over, so I excuse myself. Yikes.

Obviously, as a newbie here, I believe talking to as many women as possible (within reason) to be my primary target at this point. I also struggle to move past casual chit chat and go for the close, aka the phone number. In the meantime, I am pressing mindfulness, meditation, and improving my inner game from all faucets. If I have one overarching hurdle at this point, I’d say that I care too much about what others think of me, worrying that I am being judged in all of my actions. In the meantime, I’m keeping my head up and trusting that my practice will eventually yield results.