Sabrina Carpenter fans thrummed with anticipation as they waited in a line that stretched from the House of Blues entrance to across the River Walk, wrapping around Wacker Drive.

Some passersby guessed the line must have been for Justin Bieber or Harry Styles, but the sight was intriguing enough to pique interest from even the most self-absorbed Chicagoans, who stopped to ask, “What are you guys in line for?”

Carpenter had not headlined a performance in Chicago since her “Singular” tour in 2019, leading to the amplified sense of excitement demonstrated by the enormous line of fans willing to wait even in the brisk Chicago night air.

In the 10 minutes before the show started, the audience sang along to “All Too Well (Taylor’s Version)” until the house lights dimmed, and from the center of the major set piece of the show — a massive red heart archway — appeared Carpenter.

Carpenter was seated behind a keyboard as she played the vulnerable, stripped-down title track of her latest album “emails i can’t send” under intimate lighting, with the confident voices of the crowd nearly drowning out her changes in rhythm.

As the crowd screamed the ending lyrics, “as they say in Chicago, he had it coming,” and the mood of the venue shifted, Carpenter smiled and gestured to the crowd with open arms.

Suddenly, the red heart lit up and Carpenter abandoned the emotional opening for the sultry and dance worthy track “bet u wanna,” where she paraded around the stage in a trendy, pink Y2K-inspired ensemble and her staple heeled boots used to combat her short stature.

Carpenter transitioned into conversation with the crowd, marveling at the energy of the venue, saying, “I have a feeling you’re going to be a loud one.”

As the crowd shouted in agreement, Carpenter thanked everyone for their support of “emails I can’t send” and expressed that the last few years of her life had been tumultuous, so if anyone could relate to the themes of her songs, they could escape for the next two hours with her.

“Are any of you receiving mixed signals from someone right now?” Carpenter asked. “Well, this song is for you.”

The song was “Read your Mind,” an upbeat number about wanting clarification from a rocky relationship, a theme solidified by the subsequent “Tornado Warnings,” a song about ignoring the red flags in a relationship and lying to her therapist about it.

Carpenter exudes the talent and professionalism of a performer twice her age, as she shifted from belting to crooning and playing her own instruments, while battling technical difficulties without any visible signs of exhaustion, even in the middle of her North American tour.

After seeing a fan sign that read “I saw you play a parking lot in Cincinnati, OH,” Carpenter said she has been performing her own music since the age of 14, when she released the track “Can’t Blame a Girl for Trying.”

She fondly spoke of her fans changing her life, because she said artists start at the bottom until “they’re playing a sold-out show at the House of Blues in Chicago.”

Then Carpenter played a round of “unsubscribe,” a game she routinely plays with crowds on tour where she asks someone about where they are in their healing process from a relationship. Carpenter called on an ex-couple who bought tickets to her show before breaking up.

The crowd, and Sabrina, were shocked to learn that she and the fan had ex-boyfriends with the same name: Joshua.

It’s no secret to anyone who has followed pop culture in the past few years that Carpenter has been the subject of mass scrutiny following a messy public breakup involving fellow former Disney stars Joshua Bassett and Olivia Rodrigo.

Carpenter’s second encore was fan–favorite “because i liked a boy,” which addresses the slut-shaming and rumors of infidelity with Bassett she experienced as a result of dating in her twenties, like any other young women might.

Before she sang, Carpenter admitted that part of the fun in writing the song was imagining a crowd full of people singing that they were “home wreckers and sluts,” which the crowd did, with enthusiasm.

The loudest lyrics of the evening were “when everything went down we’d already broken up” at the climax of the song, during which hundreds of red heart balloons fell from the ceiling to thousands of outstretched palms.

At the end of the night, fans parted ways and ventured into the streets of Chicago, remaining connected by a network of red hearts as they each carried a piece of Carpenter with them.