I'll tell you my wife's worst date that happened in High School.
She has 3 pretty sisters and 2 brothers and their Dad is and Elder and substitute C.O. She and her Sisters were all asked to the High School Prom which of course they knew their parents wouldn't allow them to accept. The girls got a lucky break because their Dad had to fill in for a C.O in another state which meant the parents would be driving out of town on the weekend with the younger siblings, attending to the flock.
With the parents gone, the girls all got dressed for the prom and were picked up separately by thier dates. My wifes and her date stopped to eat at a restaraunt with a group of other kids. After the group had finished their meal and were waiting for desert to come, the booth they were sitting in collapsed and they all wound up on the floor lying on their backs with their feet straight up in the air. After that little scene ended the girls headed to the ladies room to fix their hair and dresses which were all askew. When they came back out to the lobby the guys grabbed them and told them to run....they were going to dine and dash without paying. They all ran out to the car laughing and tore out of the parking lot and headed to the dance.
The dance went fine, they had a nice time but when my wife's date (that sounds weird to say) took her home she realized that one of her sisters had the house key so she was locked out. Her date managed to find an open bathroom window and offered to climb in and open the front door. The window was located over the bathtub. On the way in he lost his balance and grabbed the shower curtain which gave way. On the way down he grabbed the towel bar which ripped out of the wall. He stumbled his way through the dark house to the front door and opened it. My wife stepped inside and he stepped outside and stood on the porch both feeling akward and not knowing what to do. Finally he said "well...I guess I'll see ya at School Monday" turned and left.
By Sunday evening her parents had returned and the girls managed to get the bathroom back together. All was well until Monday evening at the dinner table when her Dad, after asking them how things went this weekend suddenly says " So ....how was the Prom?" They were stunned, they thought they were in the clear. Apparently one of the ladies he worked with had been a Chaperone at the dance and had come up to him on Monday and told him how beautiful his girls looked at the Prom .
Luckily her Dad was a reasonable man and took it pretty well.