The Free Press
I was a really fat fourth grader. And like everyone else at my school, I had a crush on an extremely cool eighth grader. Evan wore skinny jeans and Vans, and despite his mouth being covered in blue rubber and loads of metal, his smile was perfect. I haven’t been able to get it out of my head since I first saw it in 2008.
His girlfriend was my babysitter, and I often berated her about what he was like and what they did together. She was the first girl I was ever really jealous of.
You’d think this kind of school-girl crush is one that gets filed away under Wishful Thinking or He’s Just Not That Into You: You’re 10, He’s 14, but it didn’t.
Some part of me knew we’d end up together. And so I bided my time, and made myself useful: I helped him study for his science test, which meant holding index cards as he memorized definitions for different rock formations. For that, he thanked me in his 2011 yearbook note—which I still cherish because, spoiler, we did end up together.
But first, we ended up at the same high school, where once again, he was much older and cooler than me. For four years, I watched him in the cafeteria and on the soccer field. We never spoke. He left for college.
Then one day, when he was home for the holidays, we ended up at the same party—my Senior Winterball party which he was meant to be “chaperoning.” On my way out, I asked the host—my friend’s mom—if she’d set us up. Apparently he said I was too young for him. And yet, the chubby fourth grader persisted.
A year later, once I was in college, that same mom sent me a picture of Evan and wrote, “Guess who I’m with.” I thought she was taunting me, but minutes later, she put us in a group chat together, so we could make plans when we were both back for the holidays. And we did.
At that time, I was still pining for a boy from school who didn’t like me the way I liked him. In fact, I thought that my first date with Evan would be an epic rebound—sort of poetic justice for my school-girl crush.
Instead, I met his mom.
A month later, as we were going back to school—me to New York, he to Colorado—we decided we’d try to date long distance. That was four years ago. These days, we live together. He’s the first boy I’ve ever split rent with, and I hope he’s the last.
My relationship history is unusual. I’ve never downloaded a dating app or had a one-night stand—and I’m not just saying that because my dad is a devoted subscriber.
And I have never been infected by the highly viral and contagious Gen Z creed that dating, and even love, is a total wash.
I can see my friends reading this, rolling their eyes, and thinking, Easy for you to say, you met someone early on. But I’d like to remind them, and you, and myself, that I am not unscathed by love. None of us are. I've been ghosted, broken up with, led on, cheated on (well, the guy didn’t think it was cheating, because he didn’t think we were dating. You get the picture). But I was too stubborn to give up.
What I’m really trying to say is: There’s hope. Do not get swallowed by the idea that dating is broken and love is not worth pursuing. And more importantly, do not discount someone because you think they’re too good for you. Honor the chubby fourth grader inside you. She deserves love, too. And she’ll get it. Trust me.
There are love stories everywhere. In fact, The Free Press office is full of them. So this Valentine’s Day, my colleagues and I are here to remind you to look out for romance: on Brooklyn rooftops, in your email inbox, in newsrooms, and yes, on elementary school playgrounds. Please share your love stories—whether dark or delightful—in the comments below.
Love,
Maya
Bari Weiss on a Hot Dating Tip:
Seven years ago, the world was different—and so was I. Back then, I was naive enough to think that sending a tip to a tech reporter at The New York Times about the shadow-banning of conservatives on social media would be received with a thank you. Instead, at least as Nellie tells it, she read it to colleagues and had a good laugh.
But for whatever reason—morbid curiosity, or as she reportedly told her editor at the time, a desire to “set my politics straight”—she asked to meet me for a coffee on a March afternoon in the Manhattan office.
In the years since, we got married in an Encino strip mall, moved states, moved houses, had two babies, and birthed this company.
I like to think it was me that wound up setting her politics straight. Maybe as the world shifted, the old categories didn’t matter as much. Maybe we met somewhere in the middle. In the end, readers will be the judge.
What I know for sure was sending my brilliant wife that story tip was the best decision I ever made.
Tanya Lukyanova on Brooklyn Rooftops:
“Hey, there’s a cat!”
Those were the first words my husband ever said to me. We lived in the same Brooklyn Heights building and were the only two people ever to make it to the rooftop. I would read; he’d edit piano compositions—all against the backdrop of breathtaking Manhattan views. The whole setup felt like a heavy-handed Woody Allen script. Finally, after a few glances, he worked up the nerve to break the ice—claiming he’d spotted a cat on a church roof across the street. I couldn’t see a thing, but who cared? I dashed over, thrilled he’d talk to me.
Eight years later, we’re still living in Brooklyn Heights, except now in the same apartment. We share it with our own cat—and our 2-year-old.
Margi Conklin on the Business of Words and Love:
Millennials and Zoomers, cover your ears!
My husband and I met … in the office.
It was 1997, back when such outrageous behavior was permissible. We worked together at Take a Break, Britain’s best-selling women’s weekly. He was in charge of the puzzles. I was in charge of feature stories. We sat at opposite ends of the office—a large, bleak open-plan room in North London, where staffers were allowed—gasp!—to smoke in the kitchen.
The internet wasn’t really a thing then. But an interoffice communication device called QuickMail allowed colleagues to exchange messages. Chris and I had chatted a bit at the pub after work (going to the pub after work is mandatory in Britain), and there was a definite spark. But QuickMail was the bellows that brought the embers of our romance to life.
Over messages, we traded gossip about our office mates and our tyrannical boss. We fought over which was better: U.S. basketball or English cricket. We teased each other, too—although Chris, being British, was better at that than me. Rightly sensing that I am a gullible American, he once spun a yarn about New Zealand sheep, convincing me that their legs are longer on one side than the other, enabling them to walk around mountains—but only in one direction—without falling over. (I felt like an idiot, believing that.)
All the while, QuickMail allowed us to discover our shared obsession: words. We used them to play, flirt, argue, and bond. Eventually, we arranged to meet in person regularly where we could talk about more words: mainly novels. We formed our own two-person book club in 1998, and it’s been going on ever since, except Chris is now a novelist himself (his next book is out this year!). And I am the first reader of all his work.
The words business is what brought us together. And it’s what’s kept us cooking for 27 years.
Polina Fradkin on Dating a Survivor of a Socialist Dictatorship:
Manuel emailed me after seeing my personal ad in FP Cupid, The Free Press’s under-the-radar matchmaking service. But I wasn’t a complete stranger.
A fellow immigrant to Israel—he from Venezuela, I from the U.S.—Manu first noticed me outside the synagogue in our neighborhood of Jaffa, Tel Aviv, after Friday night services. By chance, a friend forwarded him The Free Press newsletter that included my profile the following week. The email he sent me was obscene enough to catch my attention, and I figured I’d grant him one date. That was six months ago.
Not long after meeting Manu, it hit me: Fleeing an authoritarian regime isn’t just a hot perk. It should have always been a prerequisite! Here are my Top 5 reasons to date someone who has escaped a socialist dictatorship:
The worst is already behind them. Life is full of ups and downs. But no down is more down than living in a state-controlled economy. It’s only up from here for him—and that means it’s only up from here for you.
Gratitude is their default setting. If your man’s past has included hoarding tuna cans, buying toilet paper on the black market, and government-approved denim—you can bet he’ll never whine about capitalism. Every meal is a miracle. Every Amazon delivery is a blessing. Your mere presence? A gift from the God he’s now allowed to believe in!
Deep sense of duty. Toward you, toward his new country, toward getting shit done. Complaining isn’t in his vocabulary. Laziness? Never met her. He doesn’t ghost. He doesn’t flake. This man will commit—whether it’s to marriage, fatherhood, or just picking you up at the airport (which was technically our first date … and yes, he brought flowers).
Innate sense of protection. If you’re like me and your level of circumspection is “spinning like a ballerina,” you need a guy by your side who has been robbed at gunpoint regularly since he was 13. You can now literally walk the streets with your eyes closed, because he transforms into that dad from Taken the second he spots the slightest form of danger.
All the right values. Ladies, it’s 2025. We all want a man who’s normal about gay marriage, but won’t be caught dead trying to defund the police. My advice? Bag someone who has lived through rationed electricity! He doesn’t believe in culture wars—he believes in surviving actual wars. If you’re lucky like I was, you’ll have the privilege of personally explaining the meaning of Latinx to a real Latino. When it comes to what’s important, keep your eyes on the prize: hardworking, gritty, rugged, exotic accent, huge muscles.
So if you ever find yourself on a date with someone who has seen the inside of a collapsing regime, for the love of God: Hold onto him. Love him. And when he starts pointing out how your country is slowly becoming the one he fled … maybe, just maybe, listen.
Lucy Biggers on Going Viral:
This Valentine’s Day, I’d like to share the time me and my husband’s love story racked up eight million views on TikTok.
In March 2020, like many millennials, I downloaded TikTok out of lockdown boredom. After scrolling for a few days, and figuring out what kinds of things went viral, I decided to share our story. You see, Sam and I have known each other since birth—our moms are childhood friends, and our grandmothers’ friendship goes back to the 1960s. We grew up vacationing and celebrating holidays together. But sparks didn’t fly until we were 25—and maybe we’d seen enough of the world and dating (or maybe our frontal lobes had developed sufficiently) to realize, as Taylor Swift put it, “what you’re looking for has been here the whole time.”
After we began dating, I started collecting old childhood photos of us together: I found one labeled in his mom’s handwriting—”Lucy, 1 week old. Sam, 3 months old”! Another of us as toddlers in swim floaties, chatting in the grass. One from when we were awkward teenagers on a scuba-diving boat, braces-filled smiles flashing in the sun. And another photo of me jumping into his arms when we went to prom as friends.
I picked a cute song and added all these photos into the TikTok video with the caption: “When you grow up to marry your best friend.”
Overnight, it went viral. The top comment? This is like a movie!
And while it’s cool to have an origin story made for the movies, I want to remind everyone on Valentine’s Day that real love isn’t a movie. Like every couple, we’ve had our disagreements—one of them being his refusal to let me make us a famous TikTok couple after our viral success! But every day, we choose each other and our family. We’ve now got two little kids of our own—part of a life that’s more beautiful than any viral video.
Maddy Kearns on Slack Romances:
Everyone knows that the surest way to a girl’s heart is to correct her grammar. And that’s why it makes perfect sense that I fell in love with Nick while he was working as an editor, and I as a writer, at National Review magazine.
Nick joined National Review during Covid and lived in a different state, so our romance initially began over Slack, the company’s messaging app. What started as “Hi Maddy, your edit is ready :)” (note the smiley-face emoji!) soon progressed to his bold invitation to play online chess outside of working hours.
We met in person for the first time in April 2021 when I was visiting D.C., where Nick was living, for a friend’s birthday. We had a “work lunch” at Founding Farmers that lasted three hours, and squeezed in another date a couple of days later.
On the train back to New York, I wrote in my journal, “I’ve found my husband!” Fact-check: True.
Madeleine Rowley on the Power of a Good Letter:
My now-husband and I attended the same public high school in suburban Northern Virginia, but it was such a huge school that we never crossed paths. He was a year older and quarterback of the football team. I was on the yearbook committee and played field hockey. We ran in different circles, to say the least.
But on a humid June night four years later, Jay stood near the edge of the dance floor at a now-defunct Washington, D.C., nightclub called Third Edition. It so happened that I was there celebrating my friend’s 21st birthday, and Jay was there celebrating his 22nd. A red-tinted emergency light shone down on him from the ceiling like a spotlight, and I remember thinking, That guy looks familiar, and he is handsome.
We danced the night away at Third Edition but lost touch as I wrapped up my senior year of college, and he was commissioned into the U.S. Army as a second lieutenant. Right before I graduated, though, a surprise bouquet of two-dozen roses arrived at my dorm room, along with a note from Jay.
He told me he was heading to Ranger School for the next few months—one of the military’s most grueling tests of mental and physical strength. We wrote letters back and forth since he couldn’t communicate by any other means; he was in Georgia, and I had just started graduate school at Syracuse. The Army allowed Ranger School candidates to chew gum, so I included one stick of gum in each letter I sent. Thirteen years later, I still have the stack of letters we exchanged, and the rest is history.
We’ve been married for eight years and have lived all over the country and overseas. We have a 3-year-old daughter named Merritt, and this spring, we’re moving to a neighborhood that is a stone’s throw from our old high school. I think it was Shakespeare who said, “The wheel is come full circle.”
Peter Savodnik on Good Signs:
Kate and I met at 2 a.m. at a party at our friend Miriam Elder’s apartment, in Moscow.
It was 2009. Miriam was reporting for The Guardian, and I was back in Russia to report a few stories and see a few friends. Kate had just landed in town. She was a diplomat at the United States Agency for International Development (USAID). I remember leaning against Miriam’s kitchen counter and drinking something and staring at Kate and feeling, for the first time, like I’d just come in from the cold.
She was beautiful, and I loved that she thought about politics and foreign affairs and human beings in a different way than I did, and we talked all night—at Miriam's, at this bar, at the Starlite Diner, which was where expats often wound up after a long night in Moscow.
When we came out of the diner, it was light outside. Kate had to fly to Cairo that evening. I was flying to Murmansk, north of the Arctic Circle.
The next week, back in Moscow, we had dinner. I was supposed to fly to New York two days later, but I extended my stay, and then I pitched a book that would require me to spend several months in the former Soviet Union, and then a publisher bought the book.
In 2011, when Kate had to move from Moscow to Colombo, Sri Lanka, I had to move, too. I was slogging through book edits, and juggling stories in Hyderabad and Doha and Brussels and Moscow. One weekend, we went to a yoga retreat on the southern tip of Sri Lanka, and I proposed to her, and that night, we wandered down to the beach, and there were more stars in the sky than I’d ever seen. I think both of us took that—correctly—to be a good sign.
Emily Yoffe on Second Chances:
John and I had never met during our overlapping years as young journalists in D.C., even though we now know our paths had crossed numerous times. But we were on very different life paths. John had married at age 30 to a lovely fellow journalist, Robin. She was diagnosed with breast cancer just months after the wedding. I was living with, then breaking up with, a series of commitment-phobic men.
After six years of illness, Robin died. By that time, I had moved to Texas, then California. In Los Angeles I started dating an old friend of John’s, who talked about what John had been through and how, several years later, he was still single.
It turns out that John’s friend wasn’t just talking about him to me, but also about me to John. During those conversations, John had decided I was the woman he was going to marry. Of course, I was unaware of this, so when his friend and I inevitably broke up, I concluded that, at 38, I was simply destined to be alone.
Soon John got a mutual friend of ours to let me know he wanted to give me a call. That first conversation we talked and laughed for hours. Shortly after, he flew to LA for our first date. We got married four months later; our darling daughter was born 15 months after that.
We’ve been married 30 years, and we still stay up too late talking and laughing.
Adam Rubenstein on Finding Frizz:
In 2013, I was sitting in the office of The Kenyon Review. On that night, the literary magazine HQ doubled as the sanctuary for campus high holy day services. My wife says I was holding another girl’s hand (true!).
But I noticed her, with her Ohio-summer-tinged frizz, looking back at me from toward the front of the room. It was a long look. Interesting. The glimpse gave way to a conversation, an invitation to a study group, dinners at the dining hall, a friendship.
Several months into college, the relationships we were in ended. Now that neither of us were seeing other people, Frizz and I eventually had to face the music.
Indeed, Frizz had already seen me. Months into dating, my now-wife (and mother of our baby, born not-yet three weeks ago) told me that at The Kenyon Review she fell in love with me at first sight, cut ties with the guy she’d been going out with, and—unbeknownst to me—started charting the path to our together forever-ness. I’m glad she didn’t lead with that!
