Aileen Bryant was born in
Brooklyn, the third of four children. Her father, Harry Bryant, was an
architect and
builder whose
commission to construct military
barracks took the family around the country. With each move, Aileen skipped a grade, graduating from high school at age 15. She met her future husband, Meyer Osofsky, while in Cunningham Junior High School. In 1969, the couple built their dream home and settled in
Shelter Island, choosing a plot overlooking Hay Beach. The
architect Norman Jaffe designed the house. It is considered one of his most accomplished and is featured in the 2001 book
Weekend Utopia: Modern Living in the Hamptons and in the "Romantic Modernist: The Life and Work of Norman Jaffe, Architect" exhibit at the
Parrish Art Museum in 2005. Shortly after the Osofskys moved into their new home, Aileen began to participate in the community by offering the use of her home for a Shelter Island House Tour and her tennis court for local tennis tournaments. She was a steadfast supporter of the Friends of Music, the Perlman Music Program, the police and fire departments and the Red Cross ambulance corps. When Aileen won thousands of dollars as the major prize winner at the Fire Department's Chicken Barbecue, she donated it all back to the community. With her husband and daughter, Aileen donated the
Manhanset Chapel (also known as Mechanic's Hall) to the Shelter Island Historical Society. ==American Contract Bridge League==