On a winter night in Kingston, inside the stone walls of the Old Dutch Church, something a little miraculous has been happening each February. What began four years ago as a pun-powered idea cooked up among friends—Alentine’s Day—has become one of the most anticipated on the winter cultural calendar. It is a concert, yes, but also a gathering, a ritual, a love letter to community, and increasingly, the emotional center of singer-songwriter Al Olender’s creative year.
“I wanted to do a show in the winter to give people hope,” Olender says. The idea came together with her manager Drew Frankel and her best friend and collaborator Amanda Brooklyn. The pun was obvious—Al, Valentine’s Day—but the intention ran deeper. They booked the Old Dutch Church, spread the word, gathered songs, and hoped people would come. They did. And then they came back.
By the second year, something had shifted. There were familiar faces in the crowd. People sang along. Tickets sold faster. After the show, strangers came up to Olender with stories about what the night had meant to them. “I don’t know when the magic happened,” she says. “But it was there.”
Each year since, Alentine’s Day has grown a little bolder, a little bigger, a little more itself. Each iteration has a theme. Last year, it was Western—cowboy hats and, improbably, many more pairs of chaps than one would expect. This year, the theme goes somewhere else entirely: “An ExtraterrestriAL Alentine’s Day.” Sci-fi. Space. Aliens. Planet Crush.
The cosmic framing connects directly to Olender’s new album, The Worrier, releasing February 13—the same day as this year’s show. In her telling, the record lives on Planet Crush, a place shaped by yearning, longing, heartbreak, desire, grief, and the electric charge of falling in love. “I crush really hard,” she says. “And I’ve always felt a little strange in my body and in my life. Very human—but so human it becomes a bit freaky, a bit spacey.”
The album is filled with what she calls comets: songs streaking through the emotional sky, each one carrying a different shade of wanting. Ex-lovers. Current lovers. Imagined lovers. Future lovers. The ache of memory. The anticipation of connection. The album’s title suggests anxiety, but Olender hears something sturdier in it. “It’s like my shield of armor,” she says. “I’ve grown. I’ve held a mirror to myself. I’m still flawed. I still have all the mental illness of my first album [Easy Crier],” she adds, laughing, “but I’m not as scared.”
Easy Crier, released in 2022, felt rooted in grief and exposure—songs written with the emotional skin peeled back. That interior space hasn’t gone away. Grief doesn’t. “It’s something you live with,” Olender says, plainly. Her brother died 12 years ago, a loss she speaks about openly and often, not as confession but as invitation. “If I can be a safe place for that,” she says, “then okay, I’m doing a service with my music.”
When The Worrier was recorded, that vulnerability wasn’t smoothed out in the studio. Olender recorded the album live to tape at the Chicken Shack in Stanfordville with producer Nick Kinsey. No safety net. No easy fixes. Everyone in the room together—Amanda Brooklyn singing, Aubrey Haddard on guitar, David Lizmi on bass, James Felice on piano, Kinsey on drums. In one song, you can hear Olender’s phone alarm going off. She left it in.
“My favorite recordings are the ones where you can hear people’s humanity,” she says. “You hear the pain. You hear where I sound thirsty. You hear us being real people in a room together.” Live to tape felt right for an artist who thrives most when the moment can’t be replicated or controlled.
“I am not a studio girl,” Olender says, without hesitation. “When I’m in front of an audience, I feel more myself than anywhere in the world.” That wasn’t always true. Early on, she admits, she was guarded, entitled, disconnected from the audience. “I wasn’t open to the magic,” she says. That changed. Now, live performance is where she feels most alive. “It’s better than drugs. It’s better than sex. It’s my purpose.”
Alentine’s Day distills that belief into a single night. The show is built not just by Olender but by a constellation of collaborators: friends working the door, ushering the aisles, staffing the bar, running a photo booth, vending food. It is, in her words, “a true labor of love.” No one’s doing it for money or accolades. They’re doing it because they believe in the thing itself.
With that belief comes pressure. “I’m freaked out,” Olender says. “I can’t sleep. I can’t eat.” She laughs, but she’s not joking. The sense of responsibility—to the audience, to the community, to herself—keeps her up at night. “I care about this event more than anything,” she says. “I want people to be proud of me.”
Days after Alentine’s Day, Olender will pack up her Mazda and head out on her longest tour yet: 42 solo dates in two months. She’s scared. That no one will come. That she’ll lose money. That the road will take something out of her. She’s also certain she has to do it. “The person you leave tour as isn’t the person you come back as,” a friend told her recently. She felt it land in her body immediately.
Olender says she’s tired. She’s in her 30s. And she’s going anyway. “I’m a road dog,” she says. “Arf, arf.” It’s funny. It’s defiant. It’s sincere.
Back at the Old Dutch Church, on February 13, Planet Crush will come to life for one night—aliens, costumes, songs, ghosts, joy, fear, love. Olender’s brother will be there, she says. So will everyone else’s ghosts. That’s the point. To gather them all together. To sing. To feel something. To make winter a little more survivable.
