How to Have an Affair in Your Twenties
Published June 25, 2026 on serval
In your twenties, an affair should be a sexual relationship that you are hiding from your friends and peers, rather than a partner. Settling down into a traditional, publicized, and monogamous relationship has seemingly become obsolete, compared to the satisfaction of a fleeting, confidential, sexual liaison. I have very few friends with a “boyfriend” or “girlfriend,” but I have many friends who are seeing multiple people at once, sleeping with someone they shouldn’t be, or attempting to date someone informally without a public spectacle.
Privacy is a privilege rarely afforded when you’re dating in a city like New York, more remarkably now, with social media interconnection, parasocial relationships, and digital voyeurism in tow. At Manhattan’s widest point, you have 2.3 miles of privacy from East to West, and only 11.1 more than that from North to South. Relationships become known in public parks, in bars you believed weren’t popular, and on quiet city blocks. A fling is suddenly in the line of public perception after it is alluded to on an Instagram story, or you are captured together by BFA images, or you’re seen walking together in the background of a street style Tik Tok. The least conspicuous of all, it is concluded from your Instagram “Following” section alone. Discretion is a thing of the past, but I long for it more than any lover I have ever known.
On a Thursday night in July, one of my mutual friends, Bruno, introduced me to his “girlfriend” outside of the popular French bistro Lucien. I had never imagined him to be the girlfriend type, as I had only ever seen him kissing women in the common spaces of nightclubs. She was a lovely girl, and they seemed smitten in their new, and real, love as they kissed under the red awning and giggled. While I smoked and watched the lovebirds, another friend of ours asked me, “Can you believe he brought her here?” I thought it was surprising that he had a girlfriend, sure, but not that unbelievable, I explained. “No, she has a boyfriend, he lives in London,” she replied. This was real adultery, with much less discretion than the “affairs” that I was used to. I shuddered at his unabashedness in bringing a girl with a boyfriend to a place like this on a Thursday night, and proudly introducing her to people as his girlfriend.
Two weeks later, I told four female friends about Bruno’s new “relationship” over drinks. “Why would he bring her there?” echoed across the table from every direction. Nobody was shocked that they were seeing each other, but rather how overtly it was done. We were all seeing men quietly, but not because they had another girlfriend. They are men who are older or younger than us, public figures, a friend of our ex, an ex of someone we know, plainly disapproved of, or someone that we are keeping private for benign reasons. They are men that we like, but we don’t love, and we don’t wish to be formally affiliated with.
The five of us sat with our drinks, like a committee panel, and discussed whether we should share my guide with Bruno, the only con being that then we might see him somewhere with someone else’s girlfriend. I was long delegated as the savant of secret dating in our friend group. I found a slew of places within thirty minutes of Central Manhattan where we could go on a date and never be seen; saving them to a shared Apple Maps guide titled, “Use with Discretion.” Of course, it would never be airtight; we would always run the risk of seeing someone, because there is someone in all five boroughs, but litmus testing new places to see if they fit the criteria became my new hobby.
Since ending my last publicized relationship, I have had affairs with three men, all inconspicuous in their own right. One musician, one actor, and one artist; precisely the kind of men that I would hope to have an affair with in my mid-twenties. I spend most of my time in Lower Manhattan, more East than West, while living in South Brooklyn, which in itself affords me an immense amount of privacy as a starting (and ending) point. I can’t speak to how you should get someone home with you if you live somewhere socially dense. Due to the parameters I have set, I must avoid both of these areas.
You should opt for somewhere just far enough from where you live and spend most of your time. If you live in Chinatown, try Gramercy. If you live in Kips Bay, meet them on the Lower East Side. If you live in the East Village, go to Tribeca. If you live Downtown, go Uptown, and vice versa. If you both live in Williamsburg, you should take the L, separately, and meet anywhere West of Park Avenue S. If they are of public prominence, you should leave Manhattan. And if you want to ensure you will never be seen together, you should go to FiDi after 8:30 p.m. Four major neighborhoods become desolate after 8:30 p.m. on a weekday: Tribeca, Red Hook, The Upper East Side, and FiDi.
In the case of “dive bars,” the dive bar that you have heard people talk about is not a dive bar enough; it is presumably barely a dive bar at all. Look for shotty reviews, or better yet, no reviews. Don’t ever search for a place on social media. Don’t use this as an opportunity to go to that place that you’ve been “dying to check out.” Try to find somewhere that you have never even heard of. This is an opportunity to step out of your comfort zone and go somewhere new, if not entirely to you, at least to your concealed lover.
When I was dating The Actor, I often felt I had to take him to Brooklyn to avoid being stopped by someone or captured together. He had the social self-consciousness of a stray cat, and every time that we made plans, it was as if I was attempting to lure him out of a wet cardboard box. We had gone to concerts in Williamsburg, bars in Greenpoint, and restaurants in Cobble Hill, but when Brooklyn became a problem, I made one last-ditch attempt in Tribeca. I tested a new bar through two rounds of drinks with him, without a familiar face or the request, “Can we take a photo?” When we were leaving, he kissed me on the sidewalk. This place passes the test, I thought, while dropping a pin between the barren cobblestone streets.
The Artist didn’t like to drink, deeming all of my vetted bars useless, so I had to find restaurants. He also loved to dance, so I had to find clubs. We went to Astoria twice, for Egyptian-style seafood. We went to a “popular one” both times, but we knew the odds of being there on the same night as someone we knew Downtown were still slim to none. For another date, we took the ferry to a restaurant in Red Hook, followed by one singular drink at a bar within walking distance. If we were having breakfast, we went all the way to a diner on the Upper East Side, which always felt exciting. I even found a dance club in the industrial part of East Williamsburg, which satiated both my love of discretion and his love of techno music.
If it’s late enough at night, the zones that I have deemed “safe” broaden. People talk about the “marathon date,” an unusually long date that includes multiple activities and locations. I have been on many of those, and I have deemed this my version. If you plan to meet past 11:00 p.m., you can walk from 35th Street all the way to Battery Park City with minimal risk of seeing someone you know. In those 20+ blocks, time ceases to exist, and intimacy swells with each neighborhood. You can stop for a drink, you can talk to strangers and tell them that you’ve been together for years, and you will inevitably stumble upon the very kinds of places that I have spent a year carefully vetting.
When I was dating The Musician, we once met at 9:00 p.m. on the corner of Baxter Street in Chinatown and walked the whole of FiDi together. We stopped into an Irish pub for a drink, and our company couldn’t have been less familiar. We stopped at a deli for water and told the cashier that we were married, but we don’t believe in rings. We did pull-ups on the scaffolding along Broadway, using a hotel restroom to wash our hands afterward. Eventually, we landed outside the New York Stock Exchange. We sat together, with the only human in sight being a lone hot-dog vendor watching YouTube videos on his phone. The whole night felt jarringly private, as if we were the only people who knew that the Financial District existed. As we walked back to his, I dropped a pin on the New York Stock Exchange and added it to my guide.
I have a short list of places in the South Bronx and Staten Island that I have always wanted to vet, but most of my lovers have been averse to “going that far,” and that is part of the reason why they will remain a secret. I’m holding out that one day I will date someone who doesn’t want to be seen with me either, so much so that they are willing to go “that far.” I imagine us laughing playfully, riding the Uptown 6 train to get Italian food. Or taking the Staten Island ferry back with only the most touristic of company. I imagine these places would be so perfectly private that I would add a pin with each stop. I would drop one right in front of Lady Liberty, because that would be a great place to take a secret lover.
I have to credit my first boyfriend for having an actual affair and deciding that I was the woman that he needed to take somewhere more secluded. At the unbeknownst decline of our relationship, he took me to Spanish restaurants on West 200th Street, pizza shops in Bensonhurst, and burger joints in New Jersey–an entirely different state. We once traveled from SoHo to Riverside Park, just to sit in the grass together. At the time, I was obliviously enamoured by these “adventures,” but I recycle those places for my dates now, because if you’re going to cheat or get cheated on, you should at least learn something from it. Each time that I go back to one of these places, I remember my innocence and my excitement, and I hope that my new company is equally as enamoured as I once was.
When I recall my relationship, before I was on the receiving end of true infidelity, I remember that I did enjoy being loved, flaunted, and introduced to people as “my girlfriend” outside of a place like Lucien. I have since accepted that love is inherently embarrassing, particularly when you’re in your twenties. Trusting someone to become part of your life and identity is my generation’s version of choosing the parent of your child. We have all dated someone that we wish we hadn’t told so many people about, because now, we’re stuck with the association. We have all dated someone that our friends loved, or hated, a little too much, and that swayed how we felt, too.
It was humiliating to find out that most people in my inner and outer circles knew that I was being cheated on, because he was cemented publicly as my boyfriend, and he chose the most populated places in town to take other women, as if it didn’t matter. I imagine how many friends of friends had the same conversation that I recently did, “Can you believe he brought her here?” they would have remarked. I find the possibility of this being said much more embarrassing than the cheating itself. Of course, I would have liked total devotion, but at the bare minimum, I would have appreciated discretion.
The night after one of my own discretionary dates, I was sitting next to a table of twenty-something girls at dinner. I eavesdropped as they went in circles discussing the boys they had dated, boys who didn’t want to date them seriously, and the girls they knew that he had hooked up with before them. It was a style of conversation I have had with my own girlfriends too many times to count. It is a conversation that, while lighthearted, is not generally positive. We have all become accustomed to sharing the details of our lives with our closest friends, with mutual friends, and even with strangers on the internet. We do it to have something to talk about, or because we aren’t over it, or because we can’t contain the excitement of seeing someone new, or simply to prove that we are, or were, desired, wanted, and loved.
I thought about my date with the Actor the night before, and I realized that I hadn’t told anyone about him. I hadn’t told the four girls with access to my shared guide, or my best friends, I hadn’t even written about it in my journal. Nobody knew what we did together, where we went, or what we had said. Nobody could say that he was good for me or bad for me. This was entirely my own experience to navigate. That is when I realized the significance of the “Use with Discretion” guide.
To have a relationship with someone, whether emotional, physical, or platonic, that is only intricately known between two people, issomething to value. There is a strange security, even if faulty, in having the power as a young woman navigating dating to choose privacy in your life, because secrecy, for so long, has always been pushed upon a woman. The pitfall of a once hopeful relationship becomes admitting, “but he didn’t want to date me,” or hearing, “but he kept you a secret.” I think about the women who were seeing my ex-boyfriend while we were still together, and I wonder how they felt, or what their friends might have said about it over dinner. Maybe they wanted discretion just as much as I did.
A relationship being sensational news has never been exclusive to public figures. Everyone has their hometown celebrities, or those two people you knew separately who are suddenly sharing a life, or a noteworthy couple who just got engaged. A new relationship is “hard launched,” and the post amasses twice the number of shares as it has likes. I receive updates from the 22.7 square miles of Manhattan about people who live 4,000 miles away from me, because “you won’t believe who they’re dating.” We talk about the uncoupling of our parents, our friends’ parents, our neighbors, and mutual friends. We gasp over the dirty details of real affairs. We root for television relationships so much so that we almost begin to believe they are real. We do all of this because relationships that aren’t our own are fundamentally more interesting.
Relationships that are our own should be exactly that. An affair in your twenties should be a relationship that you conceal from your extended friends and peers, rather than a partner, and it shouldn’t be because you are ashamed; it should be the opposite. There is nothing wrong or embarrassing about being in love, being monogamously coupled, and happily publicizing it. Just as much as there should be nothing wrong or embarrassing about dating someone and not wanting anyone to know about it.
It is a choice that every woman should make at least once: to cherish every detail solely. To enjoy, fully, the privilege that is privacy. To have a relationship with someone that doesn’t need to be made “official,” and it is more interesting and real to you than any third parties. We have been led to believe that romanticizing our lives is necessary, and to do that, you must provide proof of how grand your experiences are. The experiences of dating, however, are imperfect and they always will be, but they are an experience that you get to have exclusively, if you want to.