Making the 1st move

I don't ask people out, I wait. A few reasons I can think of.

1) People have better plans than to go out with me. I'm not the high of the party. That's not my character. (I'm kind of boring)
2) I've no idea where to go or what to do. So how am I going to ask someone out?
3) I don't want come across over earnest or too desperate or whatever.

Othertimes I wonder if it's really that hard to ask people out. Why should it be that hard.

THEN

I'm remined that almost everytime I initiate something, it flops. So why bother.