Unconventional Wisdom: Undone by Insecurity

I finally met a girl I could trust and be with. She said I gave everything anyone could ever want from a guy but that I was insecure, and she found that repulsive. I acted jealous but did everything else right. We were together 16 months, and I learned a ton about why I was insecure. Before it blew, she gave me so many chances, but I kept trying to explain how I had changed, and that upset her. I feel I have overcome my insecurity, but explaining that to her pushed her away. She just wanted me to act secure, not tell her I wasn't insecure, which only made her think I was still insecure. I want to start over with her, but I obviously didn't know what to do before.

Your experience exemplifies an important fact of relationships: Insecurity is an unattractive trait. And some women find it especially unappealing in a man. What's more, there is such a thing as too much information. Think of the situation as akin to buying a car. Most women want to know that the model they are interested in has a motor that is strong, will take them where they want to go, and will run for a long time. They don't want to know how it was built or what adjustments have been made to get it into running condition. They simply want to be able to rely on it. She's right: Spilling is itself a display of insecurity. What is universally sexy is the opposite of insecurity, confidence, and it is one of those things that can only be demonstrated, not declared. That is not to say that vulnerability has no place in relationships. In fact, it plays an important role in fostering intimacy. We all have some fears and concerns—or develop them in challenging situations that life throws our way—no matter how confident we are, and it is the confiding of those innermost concerns that brings partners close. But that is the case only after they have established a baseline of mutual trust and respect. The confiding of vulnerabilities deepens love because it allows partners to feel authentic and fully known, and it usually elicits tenderness and support. But you were stuck on Groundhog Day, essentially starting over and over without establishing a baseline of mutual admiration or deepening the relationship. One trouble with insecurity is that it keeps you focused on yourself, and relationships grow only when partners can pay attention to each other. The feeling of security is closely related to the ability to trust people, and your propensity to jealousy suggests you are quick to perceive threats in others. It might be worth exploring in your own psyche or with a therapist why you have difficulty trusting women and how you can bolster your own sense of self. It may have to do with early experiences in your family. In order to establish a real relationship, you have to find a way to overcome a lingering sense of inadequacy and trust that there are good women out there.