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The one and only Sarah Dooley has a new record slated for release on October 23rd! While that’s still a ways away (or is it – TIME IS A FLAT CIRCLE IN 2020), she’s been gradually releasing tracks and short films in the lead-up, and we’re stoked to share the newest piece with you in the form of a video for “My Party“; the song is about the confusing feelings that get stirred up when you’re not exactly sure what you are to the person you’ve caught feelings for, and the visual companion captures that really perfectly/charmingly.

As the album title Is This Heartbreak? would lead you to deduce, the ten forthcoming tracks explore heartache in various forms. It was written about past experiences, but, oddly enough, Dooley found herself in the midst of a breakup during the pandemic. Not the ideal situation, but “It’s actually kind of good. It feels truly like a marketing ploy,” she joked with me last week over the phone.

We also talked about melding music and comedy, performing virtually, the benefits of crying on the C train and more, so get ready to internet-eavesdrop on all of that below:

So where have you been riding things out?

Ugh, Brooklyn.

Same. It’s so weird; I feel like people in this city are always a little extra bonkers in summertime, but the insanity has quadrupled with everything that’s going on.

It’s chaotic. There’s a chaotic energy in the air.

100%. Summer weirdness aside, you’ve got this record coming out in the fall. October 23rd, right? Does it feel strange to have to wait for the official release?

I don’t know…I’ve never done this before, where I release singles leading up to an album, and I think I kind of like drawing it out; I’ve worked so hard on it, and I like being able to take my time. So I’m enjoying the anticipation a little bit.

Yeah, I get that. And you’ve been doing some videos for these tracks as well, right?

Yeah, I made a short film for the three singles that are kind of backstories to the songs. (More exaggerated, funnier versions of the songs.) That was super fun.

Tell me about “My Party” specifically; is that based on a true story? You threw a party in hopes this person would show up and he ended up leaving early?

Yeah, that happened. [Laughs] Again, it’s a more exaggerated version, but it’s about that strange in-between time that sometimes happens with people where you’re not in a relationship, but it’s not nothing, either. You know? You’re just so confused about what you are. I actually think my favorite lyric that I’ve ever written is from the song, which is, “It wasn’t a thing, but it wasn’t nothing.”

It’s such a good line!

Thank you! It’s just like, I felt so many times like, “Am I allowed to feel this dramatic or emotional about this situation that maybe looks on paper to be nothing, or the other person doesn’t have the same perspective on it?” It’s just about the weird disconnect between what you’re feeling and what’s maybe happening. I wanted it to be funny, but also, I’ve definitely been the girl at the end of the party who’s crying in a pile of red solo cups. And that’s okay. [Laughs]

I also feel like this city is just a very inconvenient place to have breakups or any level of dating awkwardness. Like, I bump into the same people all the time, and it’s so annoying. I had a “wasn’t a thing but wasn’t nothing” situation with this guy, and after we stopped hanging out, I’d see him everywhere. I still see him everywhere. Or, not so much with the whole pandemic vibe, but still so uncomfortable. WHY. You wouldn’t think that would happen in a city so big, but it’s a very small world here. And you’ve been here for around a decade, right? Have you ever thought about living anywhere else?

It’s funny you should ask; I had that feeling this week. I’m actually going through a breakup right now, which is fucking insane since I wrote an album called Is This Heartbreak? about past relationships, and now when I’m releasing it I’m going through the worst heartbreak I’ve ever experienced. It’s actually kind of good. It feels truly like a marketing ploy, like the universe was like, “She’s not connected enough to the material! Let’s jazz it up!” [Laughs] Because of that, and because of the pandemic, I’m sort of like, “Ooh, I think I’d like to go on an adventure and try something new.” I’m thinking about moving out West.

That would be exciting! I’m having similar feelings of wanting to maybe leave, just because…I don’t know, the magic is kind of gone?

Right, it’s all the downsides of New York and none of the perks.

Totally. If I do stay, this will be my ten year anniversary in February, which is crazy to think about. I moved here fairly immediately after college, but during college, it’s actually funny, because some friends of mine and I somehow discovered your web series when we were in junior year. What was it called again? And Sarah?

And Sarah! Yeah, oh my god, that’s so funny! That makes me so happy.

We thought it was the funniest thing we’d ever seen! Alright, fast-forward to now and you seem to be doing a mix of comedy and music. Do you find that your creative process differs depending on what you’re working on?

That’s a really good question. I do think writing music is more of an outlet than writing comedy; I think I use music to process things, whereas with comedy, I’ll have a stupid idea in the shower and be like, “Fine, I’ll make a video about it.” It’s less of a therapeutic process for me. I’d have to think about that more, though.

And do you find that people are confused by the blend of stuff you do? I feel like it can be especially hard for people who are known for being funny to “genre hop”. (I don’t know if that’s the right wording, but you know what I mean?)

Yeah, I think people are generally pretty confused about what I do, including myself. People are like, “So what is your thing?” I’m like, “I don’t know…I do funny songs, I do sad songs…is that okay?” They’re like, “I don’t know…” [Laughs] But I was trying to do this thing in the last year or so where I’d do a standup show and tell a funny story, but then end it with a very earnest, gut-wrenching piano ballad. It was this emotional roller coaster, and it was really fun! I got some good feedback from it. But I feel like that’s my sweet spot; the song is very genuine and full of real feelings, but maybe the backstory is completely insane and funny and awkward and strange.

Absolutely. And have you always had a knack for performing? I read another interview you’d done where you said you do get nervous before shows, but do you feel like you’ve always been drawn to the stage?

Oh god, no. Not a bit. I secretly listened to musicals on my boombox and would belt ‘em out upstairs in my room, and my parents would be like, “Whoa, what was that?!” and I’d be like, “What? You could hear that? What do you mean? Nothing!” I was so, so shy, but then I went to a musical theater camp and like, “found” my voice. I went back to fourth or fifth grade, and I remember I stood up for myself in class one time, and this kid was like, “I thought you were supposed to be the shy one!” and I was like, “NOT ANYMORE!” That was like my coming out moment, but then I quickly went back into my shell. I think it took until high school to feel more comfortable doing that kind of thing. And then yeah, I guess writing my own stuff really helped. Like I feel way more comfortable performing my own comedy and music because it feels more truthful, I guess? I’m not as scared that people will judge the performance because I’m just being me, if that makes sense.

Right. Well, obviously no venues are allowing performances in NYC right now, at least indoors, and so a lot of people are having to navigate the live streamed alternative. I know you’ve been doing at home shows; how has that felt? Obviously there’s an audience, but not in the traditional sense.

It’s so strange. It makes you feel psychotic, because you’re just screaming in your bedroom, and then there’s nothing coming back. [Laughs] You feel like a psycho, but (and more so with music) it allows me to feel less nervous, because at the end of the day I’m alone in my room. People are watching, but they’re not in front of me living and breathing, and so I’m able to let my guard down even more since it feels less like a performance. And I’ve loved that. I always feel like I sound the absolutely best when I’m completely by myself, which is really inconvenient. [Laughs] This is the closest I’ve gotten to that point.

And have you been alone this whole time? Or do you have roommates and stuff?

I have a roommate, which is so lucky. She’s wonderful. But yeah, it’s just been us. And then my boyfriend, who then became not my boyfriend via the pandemic breakup. [Laughs] But yeah, it’s been super strange. My mom lives in the city so I’ve seen her a few times; I just have to bike into Manhattan.

That’s nice! Yeah, it’s been…a time, that’s for sure. I’ve actually spoken to a lot of people who’ve gone through breakups during the pandemic, which honestly, it sounds terrible, but I feel like that’s to be expected? Like, this is an unnatural amount of time to be cooped up with someone, even someone you love. It’s going to be bizarre talking to people after this is over, though. I have no idea where everyone’s at, like, in life, relationships, career…location…

I know, everyone’s scattered. Everyone’s in Maine, have you noticed that?

Yes! What the heck!

I don’t know. Everyone and their mother is currently in Maine.

The poor man’s Hamptons.

Absolutely, go off! The roast of Maine. [Laughs]

Exactly. [Laughs] So what’s your daily schedule been like, then? Do you have any semblance of a routine?

I’ve been trying to go for a walk/run in the park every day. (It’s usually a walk, but I put on running gear so it looks better.) That’s the only routine that I have, actually. I was trying to meditate, but that didn’t go well. Right now it’s mostly promoting music and trying to figure out the best way to do that, be on top of things. I’m also writing a movie right now. A lot of solitary writing and screen time have been happening, but that’s what the walk is for, to expose me to the outside world.

That’s good to hear! I think a lot of creatives have been struggling during this time, like there’s an added pressure to get stuff out. Have you had to rethink anything in terms of what you’re writing, like with the movie, to factor in this uncertain Covid future re: social distancing etc.?

It would be really smart if I were rethinking it, but I’m not; I’m just sort of hoping for the best, and hoping that someday things go back to normal and we’ll be able to make all the things that we want to. But yeah, it would be smart to write a movie about just me in my room. Maybe I’ll do that today. [Laughs]

There you go! Alright, last question. Since this is a record about heartbreak, what do you feel is the best place to cry publicly in New York City?

That’s the best question ever. How to choose? I’ve found that the C train has been very good. I mean, I haven’t been on the subway in truly a half a year, but before, the C train was so dark and loud that you could never really tell if someone was crying; maybe they were just sweaty. You couldn’t really distinguish between tears and normal bodily fluids. And I think going on a run and crying is really fun. Anything that feels cinematic is fun. And that’s just for you, you know?

Absolutely! I honestly think that’s one of the best things about NYC, is that people just let you have a moment. Like, if you’re not visibly bleeding, no one is going to interrupt you to ask if you’re okay. I love that. Alright, anything else to add before we wrap up?

I can’t stress enough that my social media presence (especially going through this breakup) is a chaotic place. I’d encourage people to follow me if they want to see a breakdown in real time. I’m spilling my feelings more than I ever, ever, EVER have online, and it’s felt so strangely good, especially because it’s so connected to what I’m talking about, which is this album about heartbreak. To reach out to strangers online and be like, “What songs do you listen to when you’re crying on the C train? Please tell me.”…it’s been super cool. The conversations I’ve been having with strangers online are giving me life.

(Follow the journey on Instagram and Twitter.)