Dating Insecurity

Why is it that the only men who are interested in dating me are painfully insecure?

These troubled souls fall into two general categories. One: he has not been with a woman for seven years, and I am the first woman he has asked out. On a first date, he tells me about how I will meet his mother and siblings and cousins, about how he’ll take me to exotic places, about how grateful he is that I am going out with him. On and on, he tells me how playful and fun he is, yet he is stiff and dull with me. He has decided already that I am the perfect woman, the right woman for him. I am like no other woman; I am “so nice, so sweet.” All the while I’m thinking, “I can’t take on this big of a project.”

When I point out to him that this is only our first date—and, as I know, but he does not yet understand, also our last date—he becomes irritated and says that I should just go with the flow. At this point, I’m thinking, “I could be home right now, scrubbing my kitchen floor. Or arranging paper clips on my desk. Or staring at a blank wall. What was I thinking!”

Two: he has had lots of sex with lots of women, but he still needs constant reinforcement and affirmation from me—even though we have not had sex at all. He is as touchy as some women—the kind I try to avoid. A benign observation, such as “You don’t strike me as an outdoorsy guy,” becomes a huge insult. Again, I think, “I can’t take on this big of a project.”

Both types of insecure men may be very successful. They may make a lot of money. They may have fantastic business sense. But for some reason, they are tragically insecure one-on-one.

It is my own damn fault, of course. I say “yes” to a date, knowing they are not right for me. I operate under the principle that everyone should be given at least one chance, and, besides, they may surprise me and transform into an engaging, emotionally healthy, dynamic, playful men. I mean, that is in the realm of possibilities, right?

Well, I guess it’s possible. But I really need to be secure in my intuition. It has never steered me wrong yet. Every time I’ve thought, “Warning! Warning! Insecure man! Back away!” I’ve been right. It’s time to say "no" from the get-go and let these men play out their insecurities with women who are willing to take on big projects.