“She’s the coolest woman in the world” I go to comment on the TikTok of Jia Tolentino talking about her three favorite books of 2025 so far. One about a contemporary couple who want to be good but their privilege limits their kindness, another about the interior life of a very desired man, and another about Britney Spears. Sadly my comment comes too late. Someone else typed it already.
Tolentino is brilliant, erudite, and works as a staff writer for the New Yorker. Her writing is succinct and scathing. Her mind 🤌🏻🤌🏻. I remember reading her seminal work, Trick Mirror, in Balboa Park during the pandemic, shaded in the shadow of trees since cut down, the freeway roaring next to us as my dog panted in the uncanny Summer heat. I felt smart reading her book. I wanted to talk about the zeitgeisty essayist dujour, because that’s what interesting adults did. I felt cool.
A quick google says the slang “cool” means “fashionable or attractive,” alternatively refreshing, as opposed to humid and uncomfortable. But I, and probably many of us, know plenty of people who I wouldn’t deem fashionable or attractive but I would still call them cool. Look at Arthur Fonzarelli, the pinnacle of cool for Boomers. If anyone dressed and acted like him now I’d probably guffaw. Then again maybe I’d fall in love with him later, like every enemies to lovers trope.
Sometimes cool means interesting, another word that means nothing nowadays. “What did you do this weekend? Oh, that’s interesting?” “How are you? That’s cool.” But for the sake of this Substack, I want to explore what actually makes something or someone different than the norm. Extra. Intriguing. Enticing. Temperature changing. Body chemistry altering.
Is cool the opposite of cringe? Is it confidence? Is it having a bunch of tattoos? Is it god given? Is it even subjective? Can someone be objectively cool? Can you become cool? Is it talent? I get talent crushes on people and find them cool.
Or is newness cool? Why do I care about the opinion of a cute guy I see at the bar more than my friends who I’ve known for decades sitting across from me? But if I saw a Kardashian walk into that same bar I wouldn’t care at all, I’d be like, “why is Khloe at Madrone on a Tuesday?”
One of many plot points of Inside Out 2 is when Ennui takes over and Riley, our pre-teen protagonist, starts behaving too-cool-for-school. Is it because being cool is to be detached? To not care? Is that why so many great actors book the roles they don’t care about? Disregarding the fact that most actors are professionally beautiful so like, duh, it’s easy for them to get roles.1
People said, and still say, Joan Didion was effortlessly cool. She didn’t go to school for writing and yet made a career out of it. She made Honolulu her artistic home. She held her baby and smoked a cigarette. She made grief sexy, in The Year of Magical Thinking for chrissakes. But why? She didn’t care? Her publishers sure cared. Her editors sure cared. She care about their opinions… within reason. It’s almost like she was blessed with an attitude that made her interesting.
Anna Wintour has defined cool for longer than I’ve been alive. Style, elegance, and predictability combine in her presence. We know she’s gonna show up to the function with the same bob and big sunglasses and she makes it look what: cool! A signature look. She announced last month she’s leaving Vogue. What?! Who’s gonna take the reins? Millennials have been waiting two decades to see what happens when the “Devil” steps down. Who will define cool for the future?
By that same token, at a certain point (and tax bracket) do we stop caring? If we lose interest do others gain it for us like a zero-sum game? For my bestie’s wedding I got a set of gel extension nails. I rarely get manicures because I can’t afford them. But I splurged for photos and the occasion. I spent over a hundred bucks on just the tips of my fingers, and people do this all the time. They don’t care. They’re cool. I cosplayed as one of them for a bit, and now I have to be careful every time I open my fridge or turn on the faucet to make sure my investment lasts, damn.
I felt cool at my bestie’s wedding. It was my first time as a bridesmaid. I was remarkably nervous, as I said last week, but it ended up being a magical weekend. I cried four times in the ceremony and two at the reception. I felt chosen, I felt important. I cared. But isn’t that the opposite of cool?
One of the groomsman asked me at the rehearsal dinner how to find their registry. The bridesmaids laughed about this later since the entire groom party was an hour late to the rehearsal, like, of course you don’t know how to find their registry on Zola. “It’s on their wedding website,” I gently told him. We exchanged pleasantries and the usual repetitive wedding banter. We parted ways.
“Alanna, I think he was flirting with you,” my other bestie, Jameelah, told me. I deflected (trying to act cool). I allowed myself to daydream about a swift, sloppy hook-up after the reception the next night. He wasn’t everything I wanted in a partner, but hey, not bad on the eyes.
My gay roommate, Jeff, came as my date to the wedding.2 I was terrified of seeing high-school people and parents already as a trans woman, but seeing them as a single woman made me even more terrified. I told everyone he was my boyfriend, while my close friends knew the truth. I wondered if I could sneakily make a show to this groomsman that it was a lavender relationship just for the weekend. I later found out not only did this groomsman have a girlfriend, but used to hook up with the bride’s arch nemesis. But I didn’t care. I played it cool.
Really the coolest part of the weekend came afterwards when I realized the only person holding me back from feeling worthy of love and affection was myself. No one cared I was trans. No one cared I was single. I was just like everyone else. The only times my minor differences arose in conversation were when I brought them up. Otherwise I blended right in. It felt good. To belong.
Maybe that’s what coolness is: belonging anywhere you are. So many acting classes I’ve taken are about cultivating this sense of belonging. Remaining comfortable in radically awkward situations, like when a camera is shoved in your face and you have to sob. The act of sobbing at all, what an uncomfortable thing. And yet some people make it look easy. Cool, even. I hope I did while I was crying with happiness, jealousy, pride, and utter joy for my best friend getting married. But actually, I don’t care how I looked, which may be the coolest thing of all.
Over Pride month I went to a few birthday parties and events, many with gay men. I saw pics of parties at the Phoenix Hotel where you can’t actually get in the pool unless you’re a guest, and other events with the ilk. These gays, so hot, with disposable income to spare, all too afraid to make out in public anymore. Like… what happened to cool? What happened to mess? You’re not cool for standing around in your two inch inseam shorts with your jock strap showing, you’re dehydrated and want dick like the rest of us. You’re not cool because you can afford the bag of powdered Calvin or Klein3 in your key pocket. Really cool people make art and change the world. Really cool people can make something fantastic out of garbage, like the alchemists on Drag Race. Only you’re too afraid to ask a guy out for fear of rejection. You need to take a beta blocker to send one email at work. You “consult” for your friend’s tech company that his billionaire dad funded and yell at estheticians who make your brows a millimeter uneven. Why did Marsha throw the first brick if you won’t even hold a guy’s hand in public anymore? You guys used to define culture and now you SF gays are just consuming it. An ouroboros with a sibilant “s.”
I went to a trivia night and a guy I don’t know was sloshed. He’d visited three bars before trivia, which started at 7 pm, by the way. He wasn’t cool. Slurring his words and leaning in close, determined to communicate and be understood. He refused water, sloppily made out with someone at the table next to us, who looked uncomfortable but like, he wasn’t forcing himself. It was awkward. He wasn’t cool. His “making out in public” was weird. I brought my dog and this drunk man’s chewed on finger nails caressed him like nibbled ball park franks combing a Turkish rug. He made me uncomfortable. And his friends who invited him because they were being nice even looked at him like, “dude, what is your problem?” Why do people do that? It’s not cool. It’s weird. Get it together, Dave.
Some of these gay guys think the only way to be cool is to be mean. I have a terrible habit of not remembering names of the gay guys I meet at parties. I meet a lot of them. They all have the same haircut. The same Barry’s tank top. The same ex boyfriends. The same four letter names. And on top of that, the only thing I can remember about them is how boring some of them are. 😬 sorry. Some of these guys came out less than a decade ago, so their cultural touchstones are Drag Race, maybe Housewives, and whatever Twitter porn they’ve bookmarked to memory from their private browser. Again, being gay used to be cool. But now it’s passé. Unless you’re a polyamorous nonbinary activist with seventeen piercings and a secret trust fund you use to pay for your friends’ top surgeries… are you really cool?
Is monogamy cool? It wasn’t in the mid to late 2010’s. “Oh, you’re not open? That’s so 90’s.” A gay friend met a cute guy at Pride, he got his number and later found out the guy was married. How tacky. When I meet people in open relationships, open marriages even, I question their intentions. How, in a world of beauty and abundance and sex and pleasure, do you think your relationship isn’t enough? Then why stay together? Be a free agent. I don’t say this to be cruel, I say this because polyamory has made dating much harder for single people. You already have a meal at home, while the rest of us are looking for ingredients.
Is this thinking old fashioned, though? That’s not cool. Are we, as humans, just looking for the next proactive person, place, or thing to grab our attention? Does that make it cool? I saw a TikTok from Diary of a CEO4 where a middle aged white woman says humans are not built for monogamy. Ooooo very incisive, very smart, very alternative thinking. But I’ve lived the non-monogamy life. I’ve been the other girl. And it’s not fun. It’s not cool. It’s unaware of itself. Make out with a stranger sure, but don’t waste their time. Falling in love is a magical event and activity, but it’s terribly expensive and can become painful. Losing money and leaving scarred isn’t cool. No matter how fashionable and attractive the person suggesting it appears to be.
Perhaps what’s cool just needs to come in and out of style. Dinosaurs became cool with Jurassic Park. Outside of particle physics and woodwind instruments, musical theatre is the nerdiest niche imaginable. But Hamilton changed culture. Not just Broadway, but everything. People remember where they were the first time they heard those songs. Lin Manuel Miranda made American History, the bane of eleventh graders everywhere, into something worth obsessing over. Fashionable, even. That damn show won awards well into 2021, a full six years after it opened in New York. But what made it cool? Was it accessibility? Ticket prices were astronomical but the soundtrack was fire and easy to find. Was it word of mouth? Everyone was talking about it, from drama club kids to Terri Gross. Who knows, but it was cool.
While walking in Hayes valley I saw two sets of tech guys talking about optimizing their time outside of work. We used to call it socializing, but now it’s “self optimization.” I assume they were talking about ways to make more money or meet more women. “Or to find a non-white wife and spend the rest of their lives trying to convince everyone she’s not their fetish” a friend of a friend cattily suggested recently. San Francisco used to be a culture center, and now it’s overflowing with valedictorians and burn outs. The former feel the need to figure out how to get laid and still go public by twenty-seven and get grand kids for their overbearing parents by thirty-two. The latter skate board and have nose bridge piercings and butthole tattoos.5 Maybe they were cool in high school but now they have thinning hair and pants that never fit them but somehow have come back in style.
Tolentino’s latest two pieces for the New Yorker have been about Gen Z having less sex than any generation before. “Casual sex can be arranged as efficiently as a burrito delivery from DoorDash” she writes as the hook. God, she’s good. But this is something I’ve heard for years about Millenials and our generational younger siblings. Is it cool to shift the blame? Is it cool to write about a problem our generations don’t care about? Every youthful ideology usually revolves around “those before us have ruined it for the rest of us.” How many times have we seen a comedian finally get serious and say the realest and saddest thing you’ve ever heard? Think the Fool in King Lear or Patton Oswalt when his wife, Michelle McNamara, passed away.
In line with that thinking, I’ll leave you with this.
I’m not above this conversation. I’m far from cool. This week I did something unkind. I hurt my friend’s feelings through text. For privacy I’ll keep it vague. I was trying to lighten the mood and read the situation wrong. Tone wasn’t received because it was through our anxiety boxes called phones, and my impact left them feeling worse. It sucked.
What is cool is that I apologized. I know with time we’ll be okay, but still. It was a shitty feeling on both sides.
Maybe we’ll never have a definition of cool. That’s what makes it so miasmic and applicable. I wonder if my family was ever cool. I have a recurring intrusive memory of my mom standing up to three girls in high school who were being cruel to our librarian. These girls were from around the way if you know what I mean, and had no trouble being violent or aggressive toward authority figures. I tried to get my mom to not engage for fear of her safety (and my reputation). They didn’t go after her but they did talk back, I was mortified. Part of me thinks my mom was cool to stand up to them, and part of me wishes she’d kept her head down. In the long run I’m more proud she stood up for the under dog, it was her super power. And that is cool, in its on way.
Okay girl, slow down, you haven’t booked since January, cool your jets
I acknowledge the hypocrisy since last week my Substack was about a gay guy-straight girl marriage. Lol
Coke and Ketamine.
His content feels just shy of problematic one moment and virtue signaling the next, he just has good SEO and fan edits his team maybe made themselves
they’re real, don’t look ‘em up
“Outside of particle physics and woodwind instruments, musical theatre is the nerdiest niche imaginable.” 💯