Just in case you thought I had no problems talking to women in public, let me assure you – it’s still a challenge sometimes.

Yesterday, I was out on my run on a beautiful Sunday morning. I ran through the park and said “hello” and “good morning” to most people I passed. I wasn’t looking to pick anybody up and I just wanted to enjoy my run. On the way home, when I was already out of the park, I spot a couple of hotties walking on the sidewalk ahead of me. They’re walking away from me so they can’t see me approaching.

There’s a part of me that thinks too much about these kinds of situations. One part of me thinks, “Hey, you have nothing to prove – you picked up Jennifer and Amber a couple of days ago, you’re dating Anna and Eve, and there are a couple of other women that my friends want to set me up with – so chill out.”

The other part of me thinks, “Here’s another perfect opportunity to practice talking to a woman in public. I can just talk to her and not ask her out. Besides, I don’t want to fall back to old habits of making excuses on why I can’t strike up a conversation with a woman I find attractive.”

Then there’s a third part of me that thinks, “OK, what am I – some kind of wannabe pick up addict? Am I going to practice until I can talk to every single attractive woman I see while I’m out? Am I going to stop my car as I’m driving because I spotted a hot woman walking on the street? Am I going to stop talking with my friends while I’m out because I spotted someone I want to talk to? I mean – how far is this going to go?”

As I’m passing them by I decide to just say hello. It’s a little awkward because there’s another group of people just ahead of the 2 women so it’s a little crowded and we’re also close to a major street so there’s a lot of noise from there. I say hello to them as I pass by and I see that one of the two women is just gorgeous. Up to know I only had a view of their backsides but now it’s confirmed – one of them is definitely a hottie.

But it feels really weird to just stop right there as I’m passing them by from behind, so I continue running until I reach the major street ahead. I then decide to run back towards the 2 women so I can stop and talk to them. I start running back and within a few seconds I have my opportunity so I do…. absolutely nothing! I run by them, again, and don’t even say a word. Man, that sucked!

I always feel it’s way better to get totally rejected than to do nothing in situations like this. At least if I got rejected, I would have felt invigorated and energized just for having the balls to start talking to them in the first place. But instead, I felt down for not going beyond saying hello to them.

Fast forward to later in the day. I was out with my family to celebrate Mother’s Day and we all stop at a Starbucks coffee shop. As we’re ordering our drinks, I spot a really attractive woman who’s also waiting for her drink. We exchange a glance and I thought I sensed some curiosity from her. She then proceeds to sit at a table and read over some books – all by herself! This would be a perfect opportunity to approach her, but I’m with my parents and sister. I’ve already tried to pick up a waitress when I was out with them, but this situation is a little different. I hesitate and decide to let this one pass. Damn it. There was even an opportunity when I had to look for some extra chairs for our table so I asked a couple of patrons if they minded if I took their unused chairs. But I didn’t use that as opportunity to ask the hottie that was sitting by herself and who exchanged a glance with me. Damn it!

When I’m feeling down for not taking action, I rely on my daily habits to keep me grounded. I’ve been going out every day on my daily morning pick up practice and today was no different. I ended up saying hello to about 10 people and I even skipped rope with some kids! There were a couple of kids on the sidewalk with their grandmother – the grandmother and one of the kids would turn the rope while the second kid would be skipping the rope. I just joined them and said, “Hey, do you mind if I skip with you guys?” So they let me have a go at it and I felt great afterwards! I’ve said it before and I’ll say it again – picking up women is about being more social with people in general and having fun.

I feel that at this point in my dating life, I should continue taking chances. I think eventually, I’ll come to a point when I won’t feel like I’m missing out on an opportunity if I spot a hot woman and don’t approach her. I remember feeling that way with my last girlfriend who I was very attracted to so I’m sure it can happen again.

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