At the heart of it, guys care too much about what attractive women will think of us. More specifically, we think that attractive women won’t find us attractive, interesting, funny, etc. I hear how a lot of women have self-esteem issues and I think guys have it, too – that we’re not good enough to be with a certain type of woman (e.g. hot, funny, intelligent) so we end up settling for what we think we deserve.

I have no problem coming up to an elderly man or woman, saying hello and start talking to them. I can also do the same with kids – I can join in the game they’re playing or say hello to them in an open, friendly way and not worry about how they respond back – in fact, I think I’m pretty good with kids.

So why do I get nervous doing the same thing with women closer to my age? I guess I feel they’ll judge me – that I’m weird or a creep. After all, who goes around talking to strangers on a regular basis? And yet, I don’t have that thought when I start talking to an elderly person – I think that they’ll think that I’m nice and friendly. Maybe because I’m assuming that they feel lonely so someone talking to them is a treat. With kids, I just assume that they love to play and be silly so I can jump right in and play and be silly with them.

But with women that I see out in public, I feel like I’ll just be one of many people vying for their attention. Or she’ll think I’m weird or she’ll get annoyed. The mental blocks that keep me from approaching women are rooted in wanting to be liked. After all, I want them to like me – to think I’m dashing, handsome, funny, intelligent, etc. But it’s hard to have both thoughts at the same time – “I hope she’ll like me.” and “Let’s have fun talking to this woman.”

The problem is: I care too much of what women will think of me.

If I didn’t give a rat’s ass what a woman will think of me, I’d start way more conversations with women than I’ve been doing. Like the woman I ran by and didn’t stop to talk to last time I went running – I cared too much what she would think of me. But with Amber, the woman I picked up at the end of a run, when I just wanted to have some fun, I didn’t care what she thought of me (because I had already picked up Jennifer earlier on in the run).

Now I’m not saying dress like a slob, don’t shave, and look like a pig. That’s more about self-respect than seeking to please others. But I do think that I spend too much time thinking unproductive thoughts like, “What am I going to say to her?”, “What if she thinks I’m weird?”, “What if she doesn’t like me?”, “What if all the other people around her think I’m weird?”

When I was out a couple of days ago with my parents at that Starbucks where I didn’t talk to the hottie that was studying by herself, I saw another interesting scene. A guy came into the store and ordered a drink. This guy was in his early to mid 40s and he had this air of arrogance about him. Just the way he was dressed and the way he walked and carried himself, I felt like this guy had a big ego. A few minutes later this hot looking woman walks into the coffee shop and it turns out they’re together. They happened to be sitting in my line of sight so I watched as the two of them talked and then the woman proceeded to sit on the guy’s lap as he rubbed her back, under her shirt. It made me wonder about the nature of attraction and how this hot woman ended up with someone who I thought was an arrogant prick. I think it had something to do with the guy appearing confident and sure of himself to the woman. I wondered if that guy cared what other women thought of him. I think not.

It’s a weird paradox that I’ve mentioned many times before – the more a guy cares what women will think of him, the less women will think of him. And the more a guy expresses himself without caring what women will think, the more women will find him attractive. Deep down, I know there’s a guy inside me that’s got so much life, pizzazz, and excitement. Why am I afraid to show that to the women I meet? If I absolutely didn’t care what women will think of my pick up approaches, I’d get way more creative, experiment with different approaches and just live life more fully.

After sharing my thoughts with you, I feel empowered and ready to keep growing and exploring. I’m thinking of setting some new goals in this area of my life. I’ll be posting more about it soon.