Debra Ostrofsky

June 1, 1954 – August 22, 2025

Debra "Debi" Ostrofsky, 71, of Fairfield, Connecticut, passed away peacefully on August 22, 2025, surrounded by the love of her family and friends.

Born on June 1, 1954, in Bridgeport, Debi was the daughter of the late Patricia and Hank Forscht. She grew up in a home filled with love, laughter, and strong family ties; a spirit she carried with her throughout her life.

Debi is survived by her devoted partner, Randall Markoya; her beloved children, Christopher Ostrofsky and his partner Tara O'Connor, and Kate Ostrofsky and her partner Conor McMorrow. She also leaves behind her cherished sister Joanne Natale; her nephew Andrew Natale and his wife Lynnette and their son Myles; and her niece Breanna Palmeiro and her husband Patrick and their son Brody. She was predeceased by her brother-in-law Al Natale.

In her early years, Debi worked at Friendly's alongside her mother and sister, where her warmth and humor quickly made her a favorite among customers. She later dedicated many years to the State of Connecticut, passionately supporting adults with special needs. Upon retiring from the state, Debi found new joy behind the bar, sharing her charm and quick wit while bartending at the 19th Hole, the Elks Club, and most memorably, the Port 5 Veterans Club in Bridgeport, a place she held close to her heart.

Known for her sass, her infectious laugh, and a playful habit of scratching an "itch" with her middle finger, Debi had a gift for making everyone feel seen and welcomed. She loved to sing and dance, and was always the life of the party, quick with a joke, a dance, or a song.

Debi's presence will be deeply missed by all who had the pleasure of knowing her. She leaves behind a legacy of love, laughter, and unwavering authenticity.

Visitation will take place on Thursday, September 4th, 2025, from 4:00 p.m. to 8:00 p.m. at Lesko Funeral Home, 1209 Post Road in Fairfield CT. Services will continue Friday September 5th, at 11:00 a.m. at St Pius X Parish in Fairfield. Interment will be held privately.

For travel directions or to leave an online condolence please visit www.LeskoFuneralHome.com.