Most of us date around in high school, in college and even for sometime after to figure out what sort of person we want to end up with and what sort of life we want.
Most people don’t meet the person they are going to spend the rest of their lives with in high school, although I do personally have a few friends that break that mold.
When she puts it that way, it does sound pretty foolish.
Since we know Rory is still trying to figure it out at the start of the series, we should be interested in what the heck she has been up to career-wise and not simply who she has invited into her bedroom.