Boylan was born James Richard Boylan, Jr., son of J. Richard Boylan and his wife, Hildegarde.[1] She grew up in Newtown Square and Devon, Pennsylvania. She graduated from Wesleyan University in 1980. From there, she moved to New York, where she was the managing editor of American Bystander magazine, the short-lived American Punch founded by the first cast of Saturday Night Live and an ad-hoc group of New Yorker cartoonists and SCTV actors and writers. Upon the demise of American Bystander in 1982, Boylan became an editorial assistant at Viking/Penguin, working for the managing editor of the Viking Press. Boylan followed with a stint as the production editor of the fiction line at E.P. Dutton until 1985.

She married Deirdre Finney in Washington, D.C., in 1988.[2][3] They have two children.

In late 1986, Boylan began a master's program at the Writing Seminars of Johns Hopkins University, where she worked with John Barth, Edward Albee, Doris Grumbach and John Irwin.

Since 1988, Jenny Boylan has been a professor of creative writing and American literature at Colby College. Boylan was a visiting professor at University College Cork, Ireland, in 1998-99. She was promoted to the rank of full Professor in May 2001, and was chosen by students as the Charles Walker Bassett "Professor of the Year" in 2000. At present, she is Director of Creative Writing at Colby. Jenny is also the Hoyer-Updike Distinguished Visiting Creative Writer for the fall of 2010 at Ursinus College.

Boylan's first book, a collection of stories entitled Remind Me to Murder You Later, was published by Johns Hopkins University Press in 1988.

Her first novel, The Planets, was published by the Poseidon Press imprint of Simon and Schuster. Loosely based upon the orchestral suite by Gustav Holst, The Planets followed the lives of several fictional characters in the real town of Centralia, Pennsylvania, which had been afflicted by an underground coal fire for several decades and housed few remaining residents. When one woman committed suicide while skydiving, she sets into effect a chain reaction of events, involving other residents of the burning town.

Picking up six years after The Planets concluded, The Constellations was published in 1994 by Random House.

Her 1997 novel, Getting In, published by Warner Books, focused on four high school students who go on quests to get into college. The novel was optioned for film by Renny Harlin and Geena Davis, and Boylan was tapped to write the initial screenplay.

Boylan's stories have appeared in publications including Confrontation, Florida Review, Quarterly West, Western Humanities Review, Writer's Digest, Southwest Review and Twelve Stories of Identity.

Her eleventh book, Falcon Quinn and the Black Mirror, follows the adventure of a young man who finds himself turning into a monster, and is sent to the Academy for Monsters to learn how to imitate "normal" humans and survive in the world.

Edward Albee commented on her in 1988: -- "Boylan observes carefully, and with love. [Her] levitating wit is wisely tethered to a humane concern. I often broke into laughter, and was now and again, struck with wonder."