Carly Rae Jepsen Recalls Kicking Glass Slipper Offstage on Opening Night of Broadway's 'Cinderella'

Jasmine Safaeian Carly Rae Jepsen

Carly Rae Jepsen knows the importance of rehearsal.

Hours before her opening night performance as the titular role in Cinderella on Broadway in 2014, the Canadian singer-songwriter rehearsed the iconic scene in which the princess swiftly exits the ball as the clock strikes midnight, leaving her glass slipper behind.

"You don't get to do the full run-through with all the tracks, the 17-pound ball gown — all the elements — until literally the day of [opening night]. I generally know where it's going," Jepsen, 36 recalls to PEOPLE. "[Actress] Laura Osnes explained to me that you stick the ballet slipper between your big toe and the rest of your toes. You run down holding it, and you lay it that way, so you don't trip over it."

In the moment, Jepsen thought everything went according to plan. "Then, I look into the distance, and I think, 'Is there a bird in the theater?' And I realize I had kicked the slipper into the audience," she says. "It was dress rehearsal, so there's no one actually there. I couldn't stop laughing, but it was that nervous laughter. I said to the director, 'Has anybody ever done that before?' He was like, 'No, and you can't do that!'"

Walter McBride/WireImage Carly Rae Jepsen

The "Call Me Maybe" performer, who's currently touring in support of her new album The Loneliest Time, spoke to PEOPLE for One Last Thing.

Last time I was out of my comfort zone: During sound check at Radio City Music Hall. We were sold out. Once the room was full, it was just excitement, but for a hot minute I was like, "What have I gotten myself into?"

Last moment of nostalgia: We had American Ballet Theatre dancer Isabella Boylston come out onstage. She gave me signed ballet slippers, and I had this flashback to doing ballet when I was little—that feeling of going to class like little ducklings.

Last indulgence: I just had a brownie, a cookie and pumpkin loaf. My boyfriend recently said, "You eat 50 percent desserts." I was like, "That's not true!" But I had M&M's in my pocket and ice cream in my hand.

Last recurring dream: I'm running on this gravel path, and then I start flying. And then someone's like, "Call the newspaper," and I wake up. I don't know — welcome to my life. I've got questions as well.

The Loneliest Time dropped Friday via Interscope Records.