On the heels of a summer of breathless touring, the folk songwriter Al Olender is looking forward to winter. It’s when she’ll put on the second annual Alentine’s Day, a show “taking back” February 14th in honor of her personal Valentine: Kingston, New York. Olender moved to the small town about 100 miles north of New York City six years ago, and recorded her first album, Easy Crier, at The Church in upstate New York. Released in the spring of 2022, that record marries grief for her brother, lamentation for the pandemic’s TV-ridden days, and the ecstacy that can be found in what’s sour.
Olender’s not heartbroken these days, though; she’s embracing her friends and owning her sexuality. In 2023, she released “Almost Famous” and “Runner Up,” singles which celebrate cinematic longing and the struggles of navigating unconventional relationship models: “There’s no secrets here, so kiss her again, at the bar that we go to with all of our friends.” Rainbow Rodeo caught up with Al Olender about coming into queerness, writing honestly about what goes on in relationships, and how finding a place to belong opened up her musical life.
This interview has been edited for length and clarity. You can read the full interview on Patreon.
Tell me about falling in love with the Hudson Valley. How does it influence you creatively?
I thought I would be someone that bounced from place to place my whole life. Maybe that comes with touring and thinking, OK, my place is on the road, and I don’t really — maybe it’s not about deserve — but I probably won’t have a place that I can call home, because I’m away so often. So when I got to the Hudson Valley, something changed for me, truly. I know it’s cheesy, or maybe it’s cliche, but there is a magic here that is unmatched, and if you have lived here I think you’re touched by it. It’s the beauty, the community, the people, the views.
I’m a total city girl: I’m from Baltimore, I lived in Nashville, and then I moved up here. Being struck by seeing the Catskills in the distance when I drive home from tour, I just get really moved by it.
But it’s more than the views: it’s the people. It’s the people I have met: the business owners, the friends, the lovers, the family. I just feel connected to this place.
It’s clear that friendship is something that means a lot to you, and that you very intentionally value. What has that meant in your music career?
I could cry. I love talking about friendship. I’ve had this childhood best friend my whole life; her name’s Abigail Dempsey and she’s an amazing musician. She plays in a band called Low Cut Connie and has her own music as well. And I’ve really come into my new friendships. Friendship means more to me than ever. I really did feel like, I don’t deserve love. I don’t deserve friendship. I don’t deserve to rely on people. I should do it all myself because I’ve lost people, and people have left me. And it’s just not true, and the Hudson Valley has taught me that. I have the most deep, loving, fulfilling friendships that I have ever had, and it’s not a coincidence that it’s in the Hudson Valley. The people that I cherish in this town have become people that — I’ve only known them for what, I’ve been here for six years — but it feels like I’ve known them a lifetime.
My music so much reflects the friendships I have, and the moments in town that we have together, and the seasons that we share. My friends are amazing. They’re so supportive of me, and to have people in your corner — you need it. Especially in this industry, you need people that can keep you in check, and that can humble you, and that can lift you up. It’s crucial to me. Maybe once in my life I would have said that my career is more important than my friends, but it’s not true. My music career would be nothing, actually, without my friends.
You’ve put on some great “hometown” shows. How do you figure out the right vibe, and what happens at an awesome Al Olender show?
Nothing means more to me than the hometown shows. Nothing! I’ve played so many shows and they’re all amazing. I love playing shows. But when I play the Hudson Valley something electric happens to me. I will do anything to make somebody entertained at an Al Olender show in the Hudson Valley. I will literally do anything. That means coordinating with my friends: we have sets, we have costumes, we have dress codes. For Alentine’s Day, I wore Amanda Brooklyn’s mom’s vintage senior recital dress. Fit me like a glove. And we did costume changes, and just wearing those really memorable, nostalgic pieces — it was so fun to have that theme. It broke my brain into wanting to do themes.
When you come to a show, yes, it’s me entertaining you and wanting you to have a good time, but you are a part of it. If I can make anybody feel included at a show, whether that be singing along, or asking somebody a question, or telling somebody I see them out there — I want it to be interactive when I’m at home, and I want the audience to be as much a part of the show, that they want to, as possible.
You told Philthy Mag earlier this year: “I think I’m moving in a direction less about heartbreak, less about loss. I’m a growing person, and growing sexual being, and I think my new music reflects that.” I’m curious about how this new direction is coming up for you in writing new music.
Gosh, I’m so glad I said “sexual being” in that interview. I probably said that and was like, “Oooh, can I say that?” But I think we can say that.
I was feeling, “Oooh, can I say that?” about quoting it back to you, so that’s validating.
Of course! I’m actually about to say “sexual being” again. A lot of my growth in relationships and myself sexually, and romantically, and in friendships has been living in the Hudson Valley. It has really inspired me to explore unconventional relationship types. It has helped me explore romance in friendships. It has broadened my music to be more relatable to singing about sex. Until I moved to New York — and this had a lot to do with the people I was around — but I was someone that was like, Alright, maybe I’ll never experience pleasure and it’ll just be what I think should feel good, or I’ll have these feelings in a way that I was taught that I should, but no. The Hudson Valley is such an open place that it’s really influenced me as a person.
And also, I’ve been getting older. I’m 30 now, and I feel more open to express myself, but I just think we need to stop putting ourselves in a box that we can’t talk about sexuality or about how not faking your orgasms really changes your life, and it can really reflect in your music as well. I have a pretty forward nature, and I am fine with that. I wish I saw that more in music. I want to hear about what really goes on in relationships. I’m not experiencing heartbreak right now but I’m still experiencing a lot of growth, whether that be in my — I’m going to say “sexual awakening” in this interview — or just in my friends, and being more open. I’m like, new to hugging. I’m really trying to embrace my friends more. I feel open to exploring myself, and my wants and my needs. And I sing a lot about it in my music, so it’s not hiding.
I feel like all of that is so present in your new single “Runner Up.” What was the writing process of that song like?
I’m definitely trying to make myself known through my music — to know myself, to have other people know me. And I have really explored my sexuality the last year or so, and my queerness, and identifying as a queer person really publicly, and hoping that inspires people to embrace themselves. I’m just finding so much beauty in different bodies, in different people, and different ways to connect with people physically and emotionally.
“Runner Up” is about living in a small town, where everybody is connected to everybody and you have to navigate that. You have to navigate jealousy and insecurity and if you’re going to explore unconventional relationship models, if you’re going to explore your sexuality, you’re going to have to really do some inner work, too.
I say this in the song, but I actually did write the song in my head walking home in the pouring rain with no umbrella. For some reason, something was happening with somebody I was smooching, and there was a sting in my heart. I was just walking down Wall Street in Kingston, and thinking to myself, Isn’t this funny? Isn’t this supposed to just happen in movies, where the tears are blending into the rain, and you’re crying over some guy named Jason? Which, there’s no person named Jason. I don’t know many Jasons. But, the biggest challenge in my self-confidence and security is navigating a small town where everybody knows everybody and privacy is hard to find. There’s a joy in it, and a bit of a hardship.
That was another question: any queer artists you’ve been listening to and loving?
Paisley Fields, who is a local gay cowboy who I’m obsessed with. Kim Petras I’ve been bumping all over tour. Joy Oladokun. And Janelle Monae, The Age of Pleasure, oh my god! Also, Carly Rae Jepsen — I know she makes music that feels like queer joy to me, but I don’t actually know — I think she’s a queer person?
Definitely. You’ve had a big touring summer — how has it been, and what’s next?
Biggest touring solo summer of my life. I’ll have to count it out, but I have played so many shows this summer. It’s been incredible. I am leaving again to open for the Gipsy Kings one more time on the East Coast, and I have some shows leading up to that: I’m playing this Heart of Midtown fundraiser put on by ReWind Kingston, an incredible store in midtown Kingston. And then I’m going to go on tour again, I come back at the end of October, I’m going to play some shows in the northeast in November, and then nothing until Alentine’s Day. I’m going to be prepping, prepping. Tentative date for Alentine’s Day is February 9. And I’ve been in the throes of touring, but I need to record a new record. So I’m telling you to tell me that.
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