Born Diana Rubin, she married the literary and cultural critic Lionel Trilling in 1929. Her parents, Sadie (née Forbert) and Joseph Rubin, were Polish Jews, her father from Warsaw and her mother from the local countryside.
She was a reviewer for The Nation magazine. Her works include We Must March My Darlings (1977), an essay collection; Mrs.Harris (1981), a study of and meditation on the trial of Jean Harris; and The Beginning of the Journey (1993), a memoir of her life and marriage to Lionel.
Carolyn Heilbrun wrote an insightful essay about her in her own final memoirs, When Men Were the Only Models We Had (2002). In his 1986 essay collection The Moronic Inferno, Martin Amis discusses the experience of meeting Trilling and her impact on New York City: 
"In New York, Diana Trilling is regarded with the suspicious awe customarily reserved for the city's senior literary ladies. Whenever I announced my intention of going along to interview her, people looked at me with trepedation, a new respect, a certain holy dread. I felt I was about to enter the lion's den — or the den of the literary lionness, which is often just as dangerous."
- Amis, Martin, "Diana Trilling at Claremont Avenue," The Moronic Inferno and Other Visits to America, London: Jonathan Cape, 1986. p.63-4.
- New York Times obituary dated October 15, 1996
- New York Times review dated October 24, 1993, of autiobiograhy The Beginning of the Journey (article title: "It's Complicated... It's Very Complicated")
- National Review obituary dated November 25, 1996.
- Diana Trilling at Find a Grave