(INSIDE EDITION) What would have been a successful date quickly turned into an epic fail with one ill-advised leap.
Much to this Pittsburgh man's dismay, the perfect evening took a turn for the worse when he tried to impress his date by jumping from one roof to another.
The man, only identified as a 22-year-old University of Pittsburgh student, fell between the two buildings, where he got stuck.
"It all began around 2 in the morning," Sonya Toler, a Pittsburgh Public Safety Department public information officer, told InsideEdition.com. "He met the young lady and took her to a rooftop. He tried to impress her by jumping from building to building."
According to Toler, the man's attempt to look "cool" caused him to fall between the two buildings with just a 16-inch gap between them.
He fell three feet and was lodged in the narrow gap for several hours until paramedics and members of the public safety department arrived at the scene.
In an attempt to free the man, authorities knocked holes through the walls of one of the buildings. It took four hours to free him.
"Fortunately, he was sent to the hospital by paramedics after he was taken out from between the buildings," said Toler.
Aside from a broken ankle, the man will most likely suffer from the embarrassment of a bad first date.