I have two garage doors.
One day, I says to myself, "Self, why don't you ever park in your garage?" Then I cocked my head and looked at my garage doors, and realized that they are both- for some reason- undersized. Like, maybe the width of my car.
So I'm drinking Bud Light one day and I decide that, no, my car will fit; I'm just not trying hard enough.
I spend 20 minutes clearing out the space in my garage and then start trying to ease the big Hemi Dodge into the small opening of the garage.
Wait... too close. Back up. Try again. Almost... Nope. Too close. I back up, try again, back up, try again, over and over until I finally ease it into the garage with about 1 inch to spare on either side of my rear view mirrors.
I exit the car, stand back and beam in congratulatory appreciation, then say the phrase:
"Yeah, I dated a girl like that once."
Hence, the phrase was born.