Are men really confidence-sucking creatures or are we victims of our own demise?

I went to church tonight with a girlfriend of mine.  They are having a three week series for singles.  He talked a lot about knowing your identity and being confident in who you are.  The service was packed, about 2000 singles (encouraging, yet discouraging?) so the wait to get out of the parking garage was pretty long.  She and I started talking about what's going on in our lives, and most importantly, if there are any potential boys on the radar.  She and I are a lot a like.  We dated roommates for years and pretty much found ourselves in the same situation while in and out of those relationships.  And now, years later, as we talk about what was said during church, we both have the same question. 

I have spent the majority of my dating life in a relationship.  It's only been within the past year and a half that I have decided that staying single to learn and grow would be beneficial to both myself and whomever I might date in the future.  Recently I told my friends, I am finally happy.  Finally confident in myself.  Finally know who I am.  Finally know what I want.  And in saying all of that, I was confident.  So, without even thinking, I started to date again. 

It's only been about 2 months since I came to this point.  And after only a short time, all of the insecurities I had in the past have resurfaced.  In less than 60 days, I have completely lost who I am.  How does this happen?  I'm not in love or even dating someone seriously.  So where is my confidence, my contentment?  Does this boy have some magical spell that keeps me wondering, doubting that I am worthy of his attention, or is it my over-analyzing that causes me to question every little text, word, conversation, date, and anything else that can be picked apart into a million pieces?  And, if it's me, how do I stop?

Maybe tonight was an eye-opener.  Maybe that particular friend invited me to that particular service because God knew I needed to hear that particular guy speak about that particular subject.  Is God waving a big red flag at me saying, "You are not ready." or, "Take a step back." Or, in my over-analyzing as I type this, is God telling me, "Relax, there's no reason to be insecure."

I could argue any side of it, but it doesn't answer my question: What is it about the male species that makes us so insecure, or is it that we fear rejection and failure so badly that we are constantly doubting ourselves? 

Kind of graphic, but the light symbolizes our thoughts and how over-analyzing can kill us!