Stella Lefty’s viral hit “Boston” continues to rise up the Billboard charts — but if the singer-songwriter wasn’t procrastinating before an early date with her now-boyfriend, Vincent Mason, it may have never existed.
“I was in Nashville on a writing trip, and I was also simultaneously seeing the guy that I’m dating now. Shout-out Vincent. Love you,” Lefty, 23, told Us exclusively ahead of her performance at Chicago’s Lollapalooza on Sunday, August 2. “I had a day where I was not being super productive, and I was going on a date with him later, and so I was like, ‘OK, I’m gonna give myself a bit of time before the date to try and get something out.’”
Lefty then wrote the chorus to “Boston” and posted it online before heading out for their date — and by the next morning, the internet’s reaction prompted her to finish the song. ASAP.
“I woke up the next morning and was just like, ‘Oh no, I need to finish the song,’” she told Us. “There is no song. So that’s really how it came to be. … It was a good thing.”
Released in February, “Boston” quickly became a breakout hit for the Chicago native, peaking at No. 3 on the Billboard Hot 100. As for that date? Seems like it was a success.
“I think he’s one of the best writers I’ve ever worked with,” Lefty told Us of boyfriend Mason, 25, who also collaborated with Lefty on the duet “Something to Lose” and is a country singer in his own right. “I think it’s fun because we’re both very different writers, and how we approach music is different. Our taste isn’t always the same. So I feel like I learn a lot from him, always.”

She added with a blush, “It’s so fun to get to work with someone you love, you know?”
Lefty’s Lollapalooza set was a homecoming for the singer, who grew up in Chicago before moving to New Orleans to study at Tulane University. She soon began posting singing videos on TikTok, eventually gaining traction for her original songs “Kiss Me” and “Thinking ‘bout You.”
Going from being a fan in the audience to a performer up on stage at the legendary festival was a surreal moment for Lefty.
“I’ve been coming to Lollapalooza since I was 15 years old,” she told Us. “When I was in high school, all I wanted to do was get permission to come here because all the cool kids are going. … Anything goes here, so to be playing here after being a fan for so many years is just so awesome.”

Because of her history with the festival, Lefty felt Lollapalooza was the perfect place to announce her debut album, Long Way Home.
“There are a lot of ties to when I was younger and what made me fall in love with music in the first place. I tried to really bring that into this album,” she teased. “I’m just so excited for there to be a body of work out in the world because I have written so many songs over the past few months that I love and think are so fun to sing. … I’m just excited for people to have more music and more to sing and dance along to if they like it.”
During her performance, Lefty gave fans a taste of her new single, “Lean In, Kiss Me,” which drops on Friday, August 7. She also welcomed Mason on stage to perform their fan-favorite duet.
“I’m going to try so incredibly hard not to get emotional because I don’t want to cry, no one wants to see that,” she told the crowd during her set. “I’m from here, I’m from Chicago, if you didn’t know. I’ve been coming to this festival since I was 15 years old, almost every single year, I was out there like you guys watching artists here on the stage. And I never believed that I would be up here.”
Long Way Home comes out on August 21.





