The last time Jenny Slate was on a global stand-up stage, she publicly embraced singledom. Disinterested in the dating apps and keen to ascend to her role as “weird aunt,” it was a declaration that she says led her on a path of “sleeping with a lot of friends,” Slate reveals in her new special, Seasoned Professional, now streaming on Prime Video. “I really miss those friendships,” she says, “wish I hadn’t done that, oopsies, sorry.”

Netflix’s Stage Fright was Slate’s debut special, released in 2019 after both her divorce from her Marcel the Shell cocreator Dean Fleischer Camp and publicized split from a former costar. But that was then, this is now: Her latest hour of comedy, directed by Obvious Child filmmaker Gillian Robespierre and recorded at the Brooklyn Academy of Music, details the “love story in reverse” that transformed her life in only five years.

After the now 41-year-old performer married her husband, art curator–writer Ben Shattuck, and welcomed their daughter, Ida (all during the pandemic, no less), she found herself back onstage—and retracing her steps. “Why am I here?” she recalls asking herself, in a recent interview with Vanity Fair. “Well, I guess because I had a baby. I’m like, well, why did I have a baby? Well, I guess because I got pregnant. Why did I get pregnant? Well, it’s weird, but it happened after this odd road trip. Why did I take that road trip? It’s sort of like toddler thinking,” Slate continues. “My daughter asks so many whys. Like, ‘Why is it raining?’ And you’re like, ‘Eh. Well, condensation.’ They’re like, ‘Why?’ And you’re like, ‘Oh, shit.’ I get to ‘I don’t know’ pretty quickly in most of it. But this one I had the whole story.”

And Slate doesn’t shirk from the pricklier parts of said story—or the personal growth required to make it happen. “I just want to share as much as possible, like as much as you can share without going to jail, that’s my limit,” she says in the special. Slate makes good on that promise, taking detours from her daughter’s birth story to unearth everything from a traumatic middle school Lactaid incident to the audition that contributed to her parting ways with her Hollywood representation. Of that ordeal, she quips, “I would love for you all to be like, What a funny, fictional joke that she’s telling about a fucking fake thing that never happened to a nice person like she.”

On the eve of her second special, Slate spoke to VF about why she won’t be telling jokes about her daughter, her staunch refusal to be chill, and what it really means to be “brave for love.”

Vanity Fair: During Seasoned Professional, you reflect on the ending of your last special, Stage Fright, in which you swore off dating. Given that you’ve now made a special about falling in love again and becoming a mother—how do you reflect on the version of yourself from five years ago?

Jenny Slate: The version of myself five years ago that was expressed in that special is accurate, but kind of pumped up by using hyperbole or comedic lyricism. Comedic lyricism while also being totally explicit, I know. But I really identify with that person, the sensitivity of heart, the exhaustion at trying to find someone that might really understand you, and also combining that with getting older and really having a clearer view of your world, and that tinge of despair. You’re just trying to create some new, weird plans so that you don’t become dull and numb.

I just feel that I have new information now, and that comes in the form of understanding that happy, healthy stories can often include really unlikely components. It’s really allowed me generally to be a bit more open-minded and optimistic because now I really live inside of a certain proof, which is that you can have a beautiful life that consists of a lot of weird, silly, wonky pieces.

When over the last five years did you realize that there is another special here and that it should be told via this love-story-in-reverse structure?

I was forcing myself to get back on stage because I was experiencing something that I think a lot of new parents might feel—that things have really been flattened and that your life is slowly trying to perk up and become a structure again. This feeling—amidst my exhaustion and disorientation—about who I am and where do I fit in. I felt afraid that maybe I just wouldn’t have the strength or the presence of mind to get back on stage. I made myself just go back up there and try to find something to talk about.

It turned out that it didn’t come back as easily as before. Part of that genuinely can be the kind-of mom brain or whatever where you just don’t have enough cognitive ability yet because your brain has actually changed. But it led to me really having to make an assessment of what had changed. And one of the things that I really like about doing comedy is that oftentimes the things that have broken me apart or really startled me are also ridiculous to me—so bizarre and extreme that they’re just laughable.

And often there’s a lot of gratitude and energy in the fact that I’m like, by the way, I’m sitting on the other side of whatever was the initial break. I’m not just crying on a toilet. I’m here, I’m maybe not showered, but I’m dressed, I’ve gotten myself together, I have the mic, I’m in a public space and I am making myself acceptable for you to see so that I don’t freak you out and I entertain you.

As I was experiencing the special, it felt like it would be such a special thing for your daughter to watch someday—this telling of how she came to be. Did that potential viewing experience loom over you in crafting the special?

I think about my daughter in the ways that I still have to be myself, and it would never serve her or me to try to make myself into a very, very plain, basic thing so as not to ever make her feel anything extreme or extraordinary. She needs to know who I am, but that said, she’s a baby and she can’t say yes or no to what I talk about. So I do feel aware of her in that I don’t want to make any statements about her personality or her place on this earth that might make her feel held down.

My mom will always be like, you were up the first night of your life. You never went to sleep. There are good days in my formative years where I would take that statement as I have a lot of energy and there are bad days that I can remember where, and my mom didn’t mean to make me feel this way, but where [I would think] I’m a really non-stop, intense person and even the people who are naturally set in this life to love me will notice that I’m a bit much, and that’s a very hard thing to think. So I just try to make it about me, but I’ve never actually thought about her watching my work because that feels really unnatural to me.

Although you state that you would “never fucking joke” about your baby because she’s perfect, do you consider a future in which you may be joking about yourself as a parent without compromising your kid?

My mind hasn’t gone there yet. I’ve always wondered if the last show will be the last one or if I should start to do something new, which I think is a good thing. I do seem to continually return to the stage, but I trust myself enough to know that if I return to the stage in a really, really public way like making a special that is on Prime and a lot of people can see it if they choose to, I will always employ my same standards for how to be respectful to the people that are in my life.

I’ve never been someone that is very interested in being on any sort of mission, but I’m very, very interested in the real ways that I affect either the person across from me at a restaurant or the person in my house or in my bed or my baby in my arms or my world at large. Especially now, I just want to be a part of something that helps people feel enlivened and hopeful and also helps them feel that strange edginess that we can all feel when we’re trying to take risks so that we can have a good emotional life. Not take weird risks in the stock market or something, I’m not interested in that. I’m not going to do any insider trading or whatever. I always mean emotionally.

On stage, you share that you were asked to audition for the role of Pennywise in the It movie. How do you decide when to divulge a show business story like that one?

I wish I could say that I thought about it a lot or had been withholding it, but the fact is, for quite a while, it just wasn’t funny to me. It was a weird situation that I basically tried to forget about. So it was sort of in the background, just dormant. Then it came up naturally in conversation about [times] when you’re encouraged to do something that you think you’re totally wrong for and how that makes you look out at the world, and it just came out as an improvised moment on stage. I was so curious about the fact that that is what my subconscious reached for. And it made me laugh so hard because it’s such a weird thing too, I mean, it’s truly embedded in my birth story in this special.

It doesn’t come from a secret trove of unspeakable embarrassments. I don’t know, so much has happened to me. I guess it will come up when it wants to surface and be a part of my art, and until then, it’s just kind of tucked away in a weird cradle in the back of my memory.

You make the act of deciding to ride a bike through Amsterdam with your future husband feel like this triumphant moment of shedding the past and trusting what happens next. Did that scene feel that way in the moment or did it only accumulate more meaning with time?

I am really afraid of riding bikes, and I even sometimes get afraid when I see people riding them and I’m not even on the bike. In retrospect, in a greater and more personal discussion of what it does mean to be brave for love, it’s all kind of a version of that thing where people say if a baby is under a car, a tiny woman can lift the car up just with the strength of her adrenaline. That was what it felt like to just try to be a normal person in the first month or so of a relationship with someone that I was really, really in love with, but afraid to say it. [I was] afraid of so much—not just bikes, but just kind of afraid of everything.

It was incredible that I did that, honestly, because I would never do that now. I feel bad for my husband, but if he were like, let’s ride some bikes right now, I would be like, absolutely not. But that said, he would never ask me to ride one now. It’s really fascinating to me what both people are flexible enough to do when they have that burgeoning love and romance for each other, and then who they’re willing to be once they’re in a healthy commitment. Because I’m sure my husband would maybe like it if I would ride a bike with him, but he also likes the feeling of setting me up for challenges that are appropriate for me and not just absolutely dreadful.

Gillian Robespierre directs the special, and you’ve had a really fruitful collaboration period together starting with Obvious Child nearly a decade ago. What has that relationship meant to you?

Oh, I feel that I owe so much to Gillian Robespierre and [producer/writer] Elisabeth Holm. I am only a seasoned professional because they are first. Our friendship is very, very close, very intimate. I think it’s rare that people can function professionally and personally and not have one of those things kind of collapse or have to take a back seat. It’s created a sort of artistic home base for me where I don’t just feel really safe, I feel incredibly excited. This is an overused phrase, but those women, they’re really everything to me. They have framed my career and continue to help me push it along.

Who do you feel most nervous about seeing the special—your husband, your therapist, Pamela, who gets quite a bit of real estate?

I’m always nervous about my mom and now that I’m a mother, that nervousness has doubled. I discussed it with my mom, like, I have this joke about Pamela, my therapist, and her subconsciously maybe playing a mother role for me, but that doesn’t mean that I don’t want you to be my mom, it’s hyperbole. And of course my mom’s so sweet and proud of me that I use my time well and take care of my mental health.

The other thing now being a mother is that every time I talk about something that has made me scared, not just sad, but scared too, I feel for my parents. If your child’s heart breaks, your heart breaks double. I’ve always known that because my parents, they’re with me, they’ve seen it all, and they have at once been incredibly strong for me, but also real about the sensitivity of all of our hearts and feelings. Maybe it’s uncomfortable for them to imagine me being upset, but weirdly, I don’t think about the explicit or sexual nature of [the special]. I just kind of dissociate—they didn’t hear those parts. They closed their eyes and went to sleep.

In the special, you declare that you’re no longer shunning the “dangerous and dark” parts of yourself, but bringing them to the surface. Was there a time in your life where you felt most prone to doing the opposite, to really shielding it all?

I’ve honestly felt that way until very, very recently. That compartmentalization or feeling of shame about parts of you that are quote, unquote “unchill,” that have a lot of fear or need, those interior put-downs can be so covert and nuanced that they can be rolled up into the ways that you also empower yourself. It can just be deeply confusing. It can be really hard to really care for oneself. It takes a lot of practice to tolerate the aspects of ourselves that for one reason or another we find to be profane or useless or embarrassing or dangerous. It just takes so much work.

I got there because I’ve done a lot of my own self-created work, whether that’s my last special or my book Little Weirds or Marcel the Shell, which I made with collaborators, but it was absolutely such a liberating, beautiful experience. Now with this special and also I’ve written another book [Lifeform] which will come out this fall, I’m just so much more sure that if I’m going to be the best that I can be, it never involves throwing a tarp over the parts of me that are the more difficult aspects. In fact, they are often the parts that make whatever I’m discussing on stage the most tender—they bring that weird, special light.

This interview has been edited and condensed for clarity.