In her new Netflix special I’m Gonna Die Alone (And I Feel Fine), Needham-bred comedian Jen Kirkman gets real about everything from her recent divorce, to being 40 and childless, to the pesky little daily annoyances that most of us accept as part of everyday life—and it’s funny as hell. We got the prolific comic, a frequent guest on Chelsea Lately who hosts a long-running podcast and is at work on her second book, to talk shop before she stops in town on Sept. 2 for a stand-up set at the Sinclair.

your new special is on Netflix—they’re doing some really cool programming. I wanted to work with them pretty much ever since they started doing comedy specials. I really wanted to work with them because so many more people see it. You know, it’s worldwide, it’s like right there in your home, you can watch it any time. And there’s very little input from them. You don’t hand it over to some editor at Netflix and they redo it, which happens sometimes at other networks. So it was almost like doing an HBO special back in the day.

Your material is predominantly autobiographical, right? Most of my material is drawn from my life, even if it’s a stupid story. I start the special with this long story about how I saw this guy who was ordering a drink. And when the waitress asked him if he wanted a lemon or a lime, he was like, “Um, whatever the green one is. I don’t know.” And I was like what the hell is happening? Then the rest of it is very autobiographical, about my family, my divorce, my life, and it’s all stand-up. I just wanted to have a really self-deprecating vibe.

Do you find that it’s a cathartic process, to channel that sort of stuff into comedy? I mean, to be honest, all the stuff I talk about takes so many years to hone and write, so the catharsis has already happened from living or you know, on a deeper level, like going to therapy or something. But I think it’s really validating when I put something out there and I hear back from people, “Oh my god I hate that too” or “I’ve had that same thing.” Then it sort of reignites the catharsis that I’ve already gone through. I’m like, oh, cool, some other people are currently in the middle of this thing, and they turn on the TV and someone is talking about it. That’s such a good feeling. So yes, it definitely ends up being, once I get the feedback, really validating.

Do you agree with the idea that you have to be a little bit miserable to be good at comedy? Yeah, I think a perfect example is Jerry Seinfeld always saying that he doesn’t have any angst and he’s perfectly well-adjusted, but he’s funny. And I’m like, “Eh, there could be something.” And he did this interview on Howard Stern where he was like, “Growing up my father wasn’t really around, my parents didn’t really pay attention to me, it was just like you’re on your own and it was no big deal.” And I totally believe that he’s not, like, tortured by it, but that is abnormal. …  I think there’s definitely something in your brain that goes, “Something’s not right here. I want to analyze this thing.” I don’t know if it’s misery, but some kind of discontent.

What did you find more nerve-wracking: your first time doing stand-up or losing your virginity? Well, this is so funny! Oh, I’m going to say losing my virginity because I was older and the person didn’t know I was one. … And I just thought, I don’t want him to find out I am one; I don’t know why. That might be a lot of pressure on him, and then [there’s that] I lied. And then, thirdly, I wonder if he’s thinking I must be so good in bed, but I don’t really know what I’m doing. And so of course none of that came to fruition. A guy is just happy that any girl will sleep with him, and everything was fine. … By the way, you’re naked usually when you lose your virginity. At the very least, you are never naked on stage.

That is a good point. Do you mind me asking how old you were? [Laughs] This is something I still have trouble saying but yes I was 20.

Oh that’s not even that old. I thought you were going to say 27 or something! It’s not that old but when you’ve lied about it for three years in college… It’s really funny actually, this is a really good example of why telling the truth is always better. My first week in college I thought—and I don’t know where I was getting this information—but I thought guys don’t like virgins and it’s going to be a real turn-off if I am one. And you forget that most people, especially in the ’90s—things were a little more innocent then—I think most people were. And this one girl on my floor was like “I’m a virgin” and everyone made it a point to, like, find her a boyfriend. And I was saying I wasn’t and a couple of the guys that I liked were freaked out by me because they were and they thought I was super experienced. And I’m like “damn it!” So I always wanted to make that into a story or something. These, like, three painful years of people thinking I was like Miss Experienced and I was like, “I’m living a lie!” I think the lying about it made it feel like it was going on longer than it was.

It’s funny because usually when I ask male comedians that same question they almost always say that stand-up was far scarier to them, and I think it’s, like you said, that they were just happy to be doing it. Isn’t that so funny? That’s such a really good point. Yeah. I think the women are more like, “is this okay?” Or, you know, we’re probably maybe a little more inclined to worry about what we look like naked or something.

You curate a playlist for all of your live shows. What are some artists you’re into right now? I really like this punk band called Against Me! that has a transgender singer. They’re so good. But I also like to put in anything mellow and cheesy. I’ll put “Is That All There Is” by Peggy Lee. I always try to put some David Bowie on it. I really like Jack White. I think that’s great coming-in music, and I feel like everyone knows him and likes him, but no one really listens to him. And then, lately RuPaul’s “Sissy That Walk” has been fun. I like to come on stage to that, even though I’m not anything like that. I’m not fabulous, I don’t have a strut, but I think it’s funny.

Anything else you want to add? Just that my parents live in Massachusetts, as does my whole family, and the virginity question—even though they’ve seen me do stand-up a million times, and I’m 40, and they know all about my life—I still think of them reading it. They’re going to be like “Jen’s not a virgin?!” [Laughs]