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Nicole Ferres arrived in Oakland about 4:30 a.m. Tuesday, ready to start her shift at Bruegger’s Bagels. She thought it was odd that there were firetrucks and police cars outside but didn’t pay much attention.

Then a police officer pulled her aside and told her about the man who was “trying to impress” a young woman and tried to jump from one roof to another.

Her first thought was: “Who in their right mind would do this?”

The answer: Grant Birdsong, 22, of Indiana Township.

Officials said Mr. Birdsong became trapped around 2 a.m. in the 3700 block of Forbes Avenue between Atwood Street and Oakland Avenue. Sonya Toler, the city’s public safety spokeswoman, said the “young man met a girl, brought her up to a rooftop and decided to impress her by leaping from one roof to the next.” The roof of Qdoba is higher than the roof of Bruegger’s Bagels.

Mr. Birdsong fell between the two buildings, breaking his ankle, and remained wedged in the tight space separating the businesses while police and paramedics worked to get him out. They had to use a jackhammer to break open a wall in Qdoba and remove him.

By the time Ms. Ferres, the general manager at the Bruegger’s shop, arrived, officials had already been working for hours. She heard the jackhammer off and on as she prepared to open the store later that morning. She invited emergency workers in for coffee and to use the restroom.

Mr. Birdsong was freed around 6 a.m. Paramedics took him to UPMC Presbyterian, where he had surgery on his ankle. Ms. Ferres didn’t see the young woman Mr. Birdsong was trying to impress. She heard that the girl “stayed that entire time they were trying to get him out.”

Public safety spokeswoman Emily Schaffer said later in the day that officials were still reviewing the incident and had not decided whether to file charges. She said damage estimates were not yet available, but she expected the business’ insurance would cover the cost.

Mr. Birdsong is a rising senior at the University of Pittsburgh, majoring in communication studies and film studies. He is the son of Tom Birdsong, a senior assistant managing editor for the Pittsburgh Post-Gazette.