Anna Holmes was the founding editor of Jezebel Magazine. She is a columnist for the New York Times Book Review and the editor of Digital Voices at Fusion.

The women I talk to are pretty pumped that Anna Holmes is participating in the #IRLProject. When I tell them that her email response said, “Sorry for the late reply; count me in! And thanks so much for thinking of me; I’m very flattered. :)” they pretty much come unglued.

What’s weird is that I don’t. Don’t get me wrong, I’m so happy. And I think it’s beyond kind that she said she was flattered. But something about this response is just so @AnnaHolmes, that I’m not surprised. Amazed that she’s committing to my little project, yes. Surprised that she’s so gracious while doing it? Not at all.

Part of it is the tone of her tweets and the way they sound almost like someone just occasionally narrating their day. She might be sharing work-related links for Fusion; she might be bitching about Amtrak service coming out of Penn Station (but in like a weirdly not snarky way); or she might be tweeting at her friends, as she was two nights before we met when she attended the Stevie Wonder concert at Madison Square Garden. Whatever the context, they are absent any “I’m an expert. Listen to me” tone and contain instead the vibe of a great host, “There’s all kinds of food in the refrigerator. Help yourself!”

We have to reschedule because of a last minute work trip (and also Mercury is retrograde) but the change works in my favor. The day after I get to New York she’s part of a panel discussion at the Lower East Side Tenement Museum where the topic is Sydney Taylor’s beautiful All of a Kind Family books. The whole thing feels very Circle of Life, these books the starting point for my lifelong love affair with New York City. Decades before I had Jewish friends who shared their faith and holidays with me; and years before I set foot on city streets, the five little sisters made me wish I was a New York kid.

Each panelist has been asked to comment on some of their favorite chapters and when Anna mentions the food, everyone in the room smiles and nods. There’s a scene where Charlotte and Gertie, two of the sisters pool their money and buy crackers and penny candy (holler if you know what a chocolate baby is) and then secretly eat them in bed after the lights are out. The freedom of shopping alone, coupled with the sweetness of sisterly camaraderie was intoxicating to me as a kid growing up in the Midwest. Anna grew up in Northern California, but it got her too.

The room is full of women who can recall tiny details of these books, and many of them want to talk to the panelists when the program ends. I loiter around the edges for awhile and finally interrupt a lengthy conversation because all of a sudden I’m so tired that I need to either leave immediately or spend the night in the Tenement Museum. Anna gives me a look that says she’s trying to place me, as I introduce myself. “Oh hi!” she says, “I saw you and thought you looked so familiar but I couldn’t figure out why! When are we meeting?” The coming Saturday is good for both of us so we set a plan and I head home. I’m up till 4 am writing the night before, but feel weirdly ok when I wake up. We email back and forth a bit and decide to meet at 1:00. I edit a little, run late and so it’s more like 1:30 when I arrive in front of a Brooklyn brownstone and call the number Anna gave me from the sidewalk. In spite of the lovely back and forth email exchange, I still I feel the anxiety of imposition rising in me as I dial. But then the door to the garden apartment swings open and there she is telling me to come in.

I don’t know if I will ever get over the sense of privilege and gratitude for the people who participated in this project.

We walk through the hallway and into a cozy family room with (New Yorkers cover your ears) a real working fireplace. She offers me a place to sit while doing a few last minute tasks and in retrospect, I have no idea what they were. The start of any meeting is always sort of awkward, so she could have painted the adjacent kitchen for all I know, but at some point I dial back in and hear her saying, “So I thought maybe today we could just do the things I would normally do on a Saturday. But first, I broke the screen on my iPhone last night and it’s bad enough that I could cut my finger. Of course I’m still using it though, so I need to get it fixed. “

She says she briefly considered taking the opportunity to get an iPhone 6, but, “I mean I don’t need a new phone and why spend $400 when you don’t need to?” Since betting that people will spend $400 when they don’t need to, seems to be Apple’s entire iPhone marketing strategy, I’m so impressed that I’m immediately down for anything this normal Saturday involves, including but not limited to canvassing for a cause, animal rescue, or vacuuming.

But she grabs her coat and mentions that she hasn’t eaten yet today, so how about starting with lunch, then runs through a list of other stops. “Do you want to meet my cat before we go?” she asks, and since this cat has infrequent mentions in her Twitter feed, I definitely do. We walk into her bedroom and there is Frog basking under a light. He’s 18, she tells me, and the bag of medicine nearby points to his failing kidneys, the same ailment that took his brother. As we discuss beloved pets, he climbs down from his perch and walks around, moving slow but steady. I’ve never seen a cat that reminded me so much of its larger Darwinian relatives, and consider what he must have been like as a kitten. Isn’t it crazy, I say, to remember where and who you were when you got him?

She locks up and we head to CPR (Cell Phone Repair, get it?) a small shop down the street where a guy with the confidence inherent only in New Yorkers, chats it up with every customer and reassures her that they’ll have it repaired in an hour or so. I’m watching soccer from the convenient waiting area chairs when I overhear him asking about getting in touch when it’s ready, feel sort of bad for eavesdropping and offer my phone number as a contact. We joke about the anxiety of not having a phone even for a couple of hours and then she takes a deep breath, hands it over and we walk outside.

Chez Moi is the perfect restaurant for people who have yet to eat at 2:30 pm, so we quickly order drinks and eggs benedict from the wildly cheerful waiter. Somewhere in the conversation I mention my children and Anna asks about them in a way that tells me she’s not just being polite, and instantly this conversation becomes one that is deeply personal. We talk about families and divorce and how to navigate through complex relationships. It’s clear she subscribes to a “Tell the Truth” philosophy, which is a gift that makes this meeting nothing like a project and so much more like lunch with a friend.

We finish up and head back to CPR where our man in Brooklyn says he was just about to call us. Anna picks out a phone case while he’s retrieving the phone and starts texting as soon as he hands it over which is when she discovers that there’s a dead spot on the screen. While we wait on a verdict from the unseen technicians, she tells me about the text conversation. “I took my dad to the Stevie Wonder concert at Madison Square Garden and it was so good, I told my friend Lizzie that she should get tickets in DC. Now she’s going and taking her mom.”

Anna’s also bought tickets for the concert in Oakland as an early Christmas gift for her sister. Since I too, tend to be evangelistic about things that I love (and maintain to this day that Savion Glover owes me money for all the people I sent to “Bring in da Noise”) it’s fun to hear about. I love that this shared and joyful experience, is worth spending money on, while an iPhone 6 is not. Mr. CPR emerges from the curtains and tells us they can fix it, but we’ll need to come back.

It’s errand time. We walk to the apartment entry where Anna keeps her grocery cart, that “only in a city” contraption that enables one to move through the neighborhood in one fell swoop, sort of a stand up wire basket on wheels. The pet store is our first stop and I head to the front where the rescue animals are hanging out, while she looks for cat food. The drug store is next and as weekly essentials are tossed into the cart, I consider how long it’s been since I shopped for things like paper towels. Two for the Pot is a little tea and spices shop that also has a tiny but perfect selection of European snacks. Anna gets loose chamomile tea. I look longingly at the chocolate biscuits, and we’re out. We’ve fallen into a rhythm at this point, stopping a conversation as we enter a store and picking it up as soon as we’re back on the sidewalk.

There’s a first birthday party the next day for the child of a good friend, and Anna says she’s decided to get a few favorite books as a gift. We scan familiar titles at BookCourt, and discuss more of the books of our childhood and the way they shaped us, Harriet the Spy, being a shared chief obsession. We pass a rack of Little Golden Books, a particular kind of comfort food for us both and she tells me that she designed the inside covers of Book of Jezebel so they would mimic the familiar repetitive patterns of the slim cardboard children’s series. She settles on Richard Scarry and a couple of great little board books and we’re out and headed to Shelsky’s Smoked Fish. She checks off what she needs and then decides to pick up a few things for her upstairs neighbor who just had a baby and is marching through an unending series of sleepless nights. Her easy banter with the counter guy is the same as it has been with everyone today. She asks for advice or assistance, shares information. She is kind and thanks people. I leave her in the able hands of the counter guy and move to the front because there is a display cabinet there with six kinds of rugelach. I buy one of each, the counter guy delivers her packages to the cashier, and the only thing left to do is go back to CPR.

The phone isn’t ready yet so we sit in the waiting area and laugh about how a day spent running errands and dragging the wire shopping cart around Brooklyn will sound to other people – It was so much fun! Really! The talking continues—babies, friends, family, life. I reach into my bag and pull out the box of rugelach and we each have one, discussing the merits of this particularly New York dessert which is basically just flavored pie crust. Then our new best friend is calling her name and handing her the phone and Anna laughs as she checks her messages and sees that the abrupt end to her earlier text conversation with Lizzie produced one of those, “Are you there? Is everything ok?” messages only found in the silence of digital spaces.

We walk back to her apartment and I know she’s got plans that night, but she says it’s fine, come in, we can talk a bit more. And here is where I ask the one question I wanted to ask, about becoming the founding editor of Jezebel magazine when that was not what she thought she was going to do. Fear of failure has been a constant companion for me and I feel anxious just thinking about taking on such a high profile job. Weren’t you afraid, I ask? “Oh yeah,” she says. “But I was tired of doing what I’d been doing and I felt like we had nothing to lose so I just worked really really hard. What’s weird is that I thought it would get easier once we were established and instead, it was harder once people had expectations.”

What’s weird is that I thought it would get easier once we were established and instead, it was harder once people had expectations

Doing small things or low profile things or below the radar things that turn into bigger things is a theme with this IRL crew. So is hard work and putting in the time and believing that life is going to turn out all right. I’ve asked all the questions I wanted to ask and gotten more time than I imagined. Still, Anna says that if I need more tomorrow, I can text her–she’ll be around after the birthday party. She stands up and gets a Book of Jezebel from the bookshelf and says she wants to give it to me, grabbing a pen and signing it while I get my coat on. As with many people, there are hard things happening in her life, some of which I’ve experienced in my own, but starting from a place of vulnerability meant a completely different day than any I could have imagined. I hug her and feel like a mom again when I tell her I know it’s all going to be ok. Walking back to the subway I have to laugh at the ever-surprising nature of this project. I don’t know what I expected from an afternoon with one of the most recognized and respected women’s voices in the country (I feel like she will die over that. Too bad, it’s true), but this meeting was as IRL as it could get. Maybe that’s her secret. Theory and high-minded thinking have their place, but the real power is in living and telling the truth.

On the subway I pull the book from my bag. There’s a signature next to her name on the title page and then this note, “Kate, thanks so much!” I read it until the C Train rolls into the 86th Street stop.