Directed by Iona senior Tyler Conroy, the cast included Cassie Alfveby as Meredith, Raquel Beato as Liz, John Bertino as Adam, Greg Bonistalli as Preacher, Mary Kate Buckley as Bailey Scott, Tyler Conroy as Taylor Grant, Annemarie Danielo as Ensemble, Moira Dollard as Lily, Alexander Fasano as Drew/Jake, Karina Gonzaelz as Alison Scott, Patty Lynch as Corey, Brigid McGlynn as Nikki, Nick Morales as Conor, Amanda Ortiz as Katie, Cassondra Richards as Abigail, Mario Rodriguez as Stephen and Sean Ryan as Sam.
"I have been an avid Taylor Swift fan since 2007, and in 2010 my friend Dale Murphy, who is an aspiring playwright, gave me It's A Love Story as a Christmas present," director and actor Conroy previously explained to Playbill.com via email. "Since 2010, I have been working on this show, and about a year ago began production on [It's a Love Story]. Taylor Swift has been my inspiration, helping me be fearless against bullies, teaching me how to speak now and accept myself, and [explaining through song] that I'll forget about the boy who broke my heart at 19 and let love begin again.
"I wanted to share her music with others in a new light to show how she's more than a girl who writes songs about boys, that she is an inspiration."
Conroy added that the cast was mostly composed of "freshmen and some who have never been on stage before. I wanted to give them this opportunity to be fearless and share their talents."
Songs from all four of Swift's albums, including "Picture to Burn," "Teardrops on My Guitar," "You Belong with Me," "I Knew You Were Trouble," "Fifteen" and "Back to December" — as well as songs that were never released as singles, such as "All Too Well," "Other Side of the Door" and "Haunted" — were featured. Conroy also choreographed alongside Kiera Savitz and Annie Danielo, and the Office of Residential Life at the campus produced.
It's A Love Story, according to the musical's Facebook page, centers around "the character Bailey Scott and her feelings for her best guy friend, Taylor. This story is about the tumultuous and emotional world of not only finding love in high school, but of finding yourself. Bailey has a hidden talent for singing that Taylor encourages her to show the world. Her feelings for him grow but she keeps them hidden to keep the friendship intact and because he is dating the Regina George of their high school, Katie. It all comes to a head when Bailey reveals to Taylor how she feels and he seems to run away from the problem. This motivates her to stand up to Katie once and for all, and finally expresses herself, through singing, at an open mic night. Sub stories include Bailey's younger sister, Allison, learning the hard way that life isn't all about dating a football player; and Bailey's best friend, Abigail, and how she manages to maintain a relationship with Sam, who has gone off to college. High school is a time when everything seems dramatic and crazy, but it's also a time when you can figure out who you are."