How trans musician Sasha Allen won the heart of America — and Adore Delano

The Jawbreaker EP also alludes to words that some people consider too difficult to understand or say correctly — from pronouns to deadnames to inclusive language — even among his high school peers.

Born and raised in Newtown, Connecticut, Allen recalls "being fed up with trying to exist as a female when I knew that I wasn't. It was an ongoing buildup," he says. "It was even more heightened in middle school, when I really tried to push it down. But the more I pushed it down, the more it bubbled up." This led Allen to start transitioning (with testosterone) the summer before his sophomore year, at age 16.

"I come from a town that is not at all diverse," Allen says. "Adore is always like, 'Your high school is like a 'movie high school.' And, yeah, that was the vibe. Those were some of the hardest years of my life."

The clearest song where Allen makes that point is "When I Forgive You," in which he gushes over his 90-year-old Catholic grandmother named Nancy Kennedy.

"My grandma is a devout Catholic who goes to church every day," Allen explains. "I wrote the song with the message of how I got unconditional love and acceptance from someone that the world might assume would reject me. If this person has the ability to be so devout and have such a belief in God and the Bible, yet also loves me and accepts me just the way I am… There's a lot of power in that. There's a lot of room for more acceptance in the world."

The adorable voicemail from his grandmother — heard in "When I Forgive You" — is from "about three years ago; she was calling me to say thanks for my Mother's Day gift," Allen says. After the song was released as the lead single of Jawbreaker, the iconic Nancy Kennedy started even "bragging about having a song written about her" to all her friends, and literally plays the track to whoever cares to listen.

Having spent his entire life in Connecticut, Allen visited Los Angeles for the first time after being cast in season 21 of NBC's The Voice and flying out to do the show. That season featured Ariana Grande as a new coach — Grande's first and only season on the show thus far — alongside Kelly Clarkson, John Legend, and Blake Shelton. While Allen never aspired to a music career where he wasn't a solo act, he and his father were cast on The Voice as a duo known as Jim and Sasha Allen. (Allen credits his dad, Jim, who is also a musician, as having taught him everything he knows about music. Jim was also on the same page as Allen about him pursuing a solo career.)

"It was shocking. I didn't think we'd make it past the first round of auditions because I didn't think we were really cut out for The Voice to begin with," Allen says. "I felt like we only got on because we would be 'good TV.' Like, I'm a trans guy, and we're a father-son duo. We also had a folkie sound I didn't think would get a chair-turn. I especially didn't think we'd get a turn from Ariana. That was in the last 10 seconds of the song, and it was the start of a really incredible journey."

Allen was 20 years old when he was cast on The Voice and turned 21 while filming. As the season went on, Allen became the first out trans contestant in the history of the U.S. series to make it to the "Live Shows" episodes. But it wasn't just America that was falling in love with Jim and Sasha Allen's talents, charisma, and life story — so was Grande.

"Ariana was fucking phenomenal during that entire experience," Allen says of being coached by Grande on The Voice. "She's a great person who took me under her wing in a way that was unprecedented on the show, and still is. I literally talked to her the other week. She's just a great person."

Well, the feeling was apparently mutual. As Jim and Sasha Allen found themselves up for elimination in the Top 11 episode and had to rely on an "Instant Save" — voted by the public — to stay on the show, Grande couldn't hold back her tears when asked to talk about her experience coaching them on the show.

"I have to [speak] now?! Are you kidding?! Oh, this is too much right now, I feel insane," Grande said in the episode while catching up with her own emotions. The pop star (and now Academy Award-nominated Wicked actress) then added: "I'm so thankful to have crossed paths with you both. I love you so much. This show is part of a bigger picture, you know what I mean? And our paths were meant to cross."

She continued, "This is such a beautiful gift: To know you, to see you perform, to grow in this space, to get to know you. I can't get over how brilliant you are. What an honor it's been to work with you, and I'm just so incredibly grateful. And I'm not going anywhere. Can't get rid of me! [laughs]. I can't wait to work together, and support you forever."

While talent-based competition shows on TV have developed a bad reputation in regard to coaches, judges, and/or hosts who make certain promises to contestants but eventually distance themselves from the cast members, Allen has nothing but love and absolute praise when asked about Grande's coaching on The Voice.

"Toward the end of the season, we were trying to figure out what to sing for our final 'Save' song. We knew we had to prepare for that because we didn't do well the week before, so we thought we might get voted off," Allen recalls. "Ariana was on FaceTime with my dad and I for three hours, from 10 p.m. to 1:00 in the morning, going over songs. This was on her own time. If you needed her, for anything, she was always there."

In case you didn't know: The winner of The Voice typically receives a cash prize of $100,000 and signs a contract with Universal Music Group. Grande herself is signed to Republic Records, which operates under UMG and has a star-studded catalog of artists such as Taylor Swift, The Weeknd, Lorde, Drake, Nicki Minaj, Stevie Wonder, and Grande's Wicked costar, the 2024 Out100 Icon of the Year herself, Cynthia Erivo.

As season 21 came to an end — with Jim and Sasha Allen being eliminated in the semifinals — Grande not only stayed in touch with them, but also pulled a few strings behind the scenes to support these talented artists she had coached, championed, and actually bonded with.

"My dad and I were the last ones on Team Ariana, and we obviously didn't win the show, but Ariana went to her label to facilitate an opportunity for my dad and I to release an EP together under that label," Allen says. "It did come out, and it's called 16 Borders. We released it a couple of years ago [2022]. My dad's an incredible singer-songwriter who taught me everything I know. That EP is all of his songs that he wrote when I was a baby. So we sang them together and put them out as an EP."

Allen continues, "And then, as an independent artist, I also got a deal. It was a lot of meetings in the months after The Voice. I made a move to L.A. because I was like, 'I gotta do something with this.' You're booted off a reality show and you go from the top of the world to 'what the fuck do I do now?'"

"I was really set on taking the eyes that were on me and putting it somewhere. 'I can't let this die. This wasn't all for nothing.' That can very easily happen, by the way, and that's the brutal reality of television," he adds. "So I moved to L.A., my dad and I recorded that EP, and I kept working on music while trying to figure out life in my early 20s."

Despite his young age, recent Hollywood move, and the overall uncertainty about his music career after The Voice, Allen says that Grande "brought me in there [Republic Records], and presented me, and said that she had a lot of belief in my writing. I've been writing music since I was 12, and she saw that in me. As she brought me in, I felt like other people at the label saw that in me, too."

Unfortunately, Allen's years signed to Republic didn't go well — a journey that is all too familiar to so many artists. "It just ended up being a tale-as-old-as-time record label situation where there's a lot of holdup, trying to change things, and not being heard," he reflects. "I was the smallest fish ever in this massive ocean that is UMG. It's a massive record label with the biggest artists in the world. It felt like a dream, at first. It had been a dream, my whole life, to be signed to a record label. I was like, 'Oh my god, this is great. I'm not going to fade away.' But it just turned into the typical thing: I was in an all-encompassing contract that didn't turn out the way I would imagine."

Allen also highlights the irony of the situation. "I was weirdly booted off The Voice in the semifinals but ended up with the grand prize of The Voice — minus the $100,000. But I got the same record label contract that the winner of The Voice gets. I tried to make it work, but it was difficult."

Allen's experiences signed under Republic Records are the prevailing theme of the opening track from Jawbreaker, "David & Goliath."

Allen underscores that things didn't work out with the label for reasons that had nothing to do with his former coach on The Voice. Grande had the best intentions bringing in Allen and his dad to such a large platform — her own label. Sadly, this is an industry-wide issue concerning most up-and-coming artists who get signed to several different record labels.

Back in the day, Lady Gaga was famously not signed by music executive L.A. Reid. Earlier this year, Chappell Roan won the Grammy Award for Best New Artist and delivered a speech asking record labels to be more supportive of emerging talent. Allen makes it clear that he and Grande still keep in touch, and that his experience with the label was something no one could've fixed.

It is around this time of professional turmoil that Adore Delano enters Allen's life.

"I met her on November 1, 2024. The day after Halloween. I got on her Instagram DMs at 9 p.m. and I was like, 'Are you free?' I had never met her. We had never interacted other than me sliding up on her selfies and being like, 'You're so stunning.'"

So did Allen just literally slide into Delano's DMs without any context?

"Yeah, I just slid into her DMs, which is a really great message to everyone out there: Shoot your shot. I just did it, and it worked! She was like, 'Well, I wasn't going to go out tonight.' I got in an Uber, went to WeHo, and met her for the first time."

"Adore just took my breath away the moment that I met her," Allen recalls. "She took my breath away for the rest of the night. And I got a second date, which was… We spent nine hours together doing absolutely everything we could do. Then we had another date that was, like, 12 hours. I just completely and totally fell in love with her. I am totally, completely, just like, 'I've found it.' I totally found it in her. I've never met someone like her in my entire life. And no one had snatched her up! I don't know how she was single."

As they spent more time together, the parallels between them became clearer and more interesting. Delano, also a singer, had experiences competing on American Idol, and then a breakout run on RuPaul's Drag Race that turned her into an even bigger star. As expected, she also had all sorts of wild experiences as a new artist in the music industry.

In fact, "Adore actually played a huge part in me asking [the record label] to drop me," Allen reveals. "Literally on my first date with Adore, we were at The Grove in West Hollywood eating a salad, and we didn't even know each other yet. I told her I was in this situation… But, at the time, I didn't want to be dropped. I thought, 'Oh, then the last three years of my life would be a complete and total waste.' That's how I felt when we met."

"But Adore was like, 'You need to get the fuck off of that label. Your voice and your guitar are your weapons. I can literally see in your eyes that you need to do this.' She was like, 'They fucking shelved you. You're shelved right now. They're not doing shit with you. You need to get off of that label.'"

Allen says that he was stunned not only by Delano's presence — and his clear crush on her — but also the way she was able to see right through him, immediately. "I never had someone say that to me before, like, 'You don't need them. You don't need that record label.' She gave me a lot of courage and a lot of belief in myself to finally be like, 'Please drop me off this label. I feel like I'm going fucking crazy. I am begging you to drop me.'"

It only took a week after getting dropped from the record label — by his own request and insistence) for Allen to release his first single, "When I Forgive You," noting that he's been working on the Jawbreaker EP "with a setup in Adore's closet [laughs]. I have a mic, a computer, and I can play all the instruments myself, which I'm fucking really thankful for."

In the romantic and interpersonal sense, Allen highlights his relationship dynamics with Delano. "I started medically transitioning and into testosterone when I was 16. She started transitioning at 33. But it's so cool," he says. "It's a very unique experience, and we get to talk about a lot of things. We get to discuss it. I've never had that with anyone else… We can just sit on the kitchen counters at midnight and just talk about shit that we both understand to our core. It's really awesome."

Allen reveals that two songs on Jawbreaker are about Delano: "Kick Us Out Again" — about getting kicked out of a WeHo club for spending three hours snuggling in a booth — and the title track, "Jawbreaker," referencing Delano's favorite movie of all time.

Did Allen make things official with Delano?

"Yeah, I asked her to be my girlfriend," he replies. "It was the first time I was in her apartment. I got down on… Well, do you know Love Is Blind?" Of course, I tell him. He replied, "So we kept making jokes that we were like on Love Is Blind, in the pods. We're weird next to each other. So, at one point, I said something about the dishwasher being broken, and as she came to see it, I got down on one knee — Love Is Blind-style — and asked, 'Will you be my girlfriend?' Very cheese ball, but she liked it."

Allen has dozens of aspirations for his career moving forward. But considering the times that we're living in, I ask if he — as someone who started his gender journey in high school — has any advice to offer trans youth at a difficult time like this.

"Do not let them steal your joy. There are people fighting for you. There are people who love you. There are people who care about you," Allen replies. "The joy that comes out of being trans is the greatest gift you will ever experience."

"Other than what people do to hurt us and perceive us, being trans is beautiful. The more you live, and the more life you experience as a trans person, the greater that it gets. I'm telling you that it's worth it. And to any kid who's in a fucked-up situation with parents who don't accept you, or feeling fucked by the government… Please know that there are people fighting for you; people who love you. There is life on the other side. You'll find people who understand you, and it'll change your life."

Sasha Allen's brand-new EP, Jawbreaker, is now streaming on Spotify, Apple Music, YouTube, and Amazon Music. Fans can also buy merch on SashaAllenMusic.com.