Related to tailgating; Taildating take place on the road when someone appearing to be very hott drives past you. You glance at them only long enough to wish you had better view, so you speed back to to try and cath them. In the process you end up tailgating them, and since your actually interested in the driver, its referred to as taildating.
"Whoa, did you see that chick that just flew by in that Jeep, she was hot! I'm going to try and catch back up and see if I can taildate her."