Care labels for the person you're dating
Some people are machine washable, some are dry clean only
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Now that Dating Season is in full swing and you have met heaps of hot flakey people on dating apps and that one mildly attractive but super wholesome person through your married friend, who insulted you by thinking this person was remotely in your league, you are wondering how to stop torching every romantic connection you make and finally build a durable, drama-free relationship with someone other than your doorman, who silently judges the volume of people who mispronounce your name and enter your apartment at 10:18pm and leave in various states of disarray at 1:05am. It turns out that maintaining a romantic relationship requires knowledge of how to handle the unique person you’re dating.
The people you date are just like clothing: available in all different shapes, sizes, and price points, and they can be tried on, worn, and returned to the shelf. Also like clothing, the people you date come equipped with care labels, only rather than being discreetly tucked inside the garment with cryptic symbols that only midwestern moms can decipher, the care label on whomever you’re dating is visible in plain sight: etched into the lines on their face, written in their family history and socio economic status, painted by their behavior, and scrawled all over their social media.
You may wish to ignore these evident care instructions and continue to treat every person you date like (literal) carbon copies of one another. This works if you’re attractive enough to be featured in more than 100 photos with BFA watermarks that appear in a Google search of your first name and just the first two letters of your surname and if there are at least three buildings named after your grandfather in the business districts of a major city.
For the rest of you, simply identify from the list below which type of person you’re dating, scroll down to read their care instructions, and decide based on their Care Complexity Level if they’re hot enough to justify how difficult they’re going to be.
The 20something Male
The 20something Female Who Works
The 20something Trust Fund Girl
The Generic 30something Male
The 30something Tech Bro
The 30something Finance Bro
The 30something “Girl Boss”
The 30something Female Who’s Freaking Out
The 40something Man-child
The 40something “Late Bloomer”
The 40something Independent Woman
Any Gender of Human Over 50
1. The 20something Male
The 20something Male is the simplest type of person to date and also the simplest form of human. They can be found anywhere, are inexpensive to acquire, and do not inspire or require a great deal of emotional attachment—like gym socks. Also like gym socks, no one notices them unless they are unusual, so any attention you lavish upon a 20something Male will be met with unbridled gratitude and sloppy enthusiasm—like a puppy. Also like a puppy, they eat and drink anything, will take all of your communications at face value, and will be surprised and delighted when you keep turning up.
To care for your 20something Male, feed them food that comes in white boxes, communicate via text or DM in simple and succinct language between 9pm and 3am, and take them to the social equivalent of a wash-and-fold laundromat: dive bars with TVs that broadcast sports.
Care Complexity Level: 0.7 / 10
20something Females require more care than their male equivalents, because most women have more emotional depth than men, and women ultimately become fully formed people with unique identities. The are two basic varieties of 20something Female, and both enjoy the highest level of dating optionality in the romantic marketplace, because every type of male wants to date them:
2. The 20something Female Who Works is the most optimistic and joyful single human in the dating population, because they have not been coddled, become prematurely jaded, or gone totally batshit. You can maintain your 20something Female Who Works with any experience that shows you’ve listened even a tiny bit to her interests. For example, she is probably obsessed with Gentile gelato, enjoys sitting at the bar at Dante and at an outdoor table at Whitehorse Tavern, and the maitre’d at Sant Ambroeus adores her almost as much as the flower dealer at the Farmers Market. The sooner you take her to Cold Springs, Runyun Canyon, or Hampstead Heath for a hike followed by an early dinner, the sooner she will introduce you to her parents in Connecticut, Pasadena, or Surry.
20something Females Who Work require a level of care that is similar to that one midnight blue designer t-shirt that you always wear on first dates: machine wash cold and hang dry.
Care Complexity Level: 2.7 / 10
3. The 20something Trust Fund Girl has been shielded from practical reality by family wealth, and the guy she dated throughout college and during her first two years in the city was conditioned to her extreme sense of entitlement, so you will either need to fall in line or optimize her for a less accommodating reality. She is from Greenwich, Short Hills, Oyster Bay, Laguna Beach, West Sussex, or Aix-en-Provence and now lives in Nolita, the West Village, Tribeca, West LA, West London, or the 7th arr.t., respectively. She works to have a place to go during the day so that she can justify to her parents the expense of a live-in housekeeper and full-time dog walker, even though she only has a foster dog a few days each month for IG content.
This type of 20something Female who does not really work requires significantly more nuanced care than a 20something Females Who Works. Through first date place-dropping and her list of Places on Raya, she will provide you with approved venues to take her—any membership club other than Soho House, Torrisi, Theodora, Le Veau d’Or, Julie’s Notting Hill, or Ladyhawk WeHo. Always compliment her on whatever she’s wearing, and never take a bite of food at a restaurant before she has photographed it and indicated that she is satisfied with the photo. You will never be tagged or included in any photo, because she is more relatable to her social media following as an independent single woman, even though she is highly dependent. Your relationship with her will fail if your communication behavior does not fall within narrow parameters: prior to date #4, wait at least 7 hours to respond to any text, and do not watch her IG stories once she adds you (NEVER add her first). From date #5 onwards, you will be expected to respond immediately to texts, heart anything she posts online within 19 seconds, and pick up the phone if she calls while you are negotiating the end of a war.
The 20something Trust Fund Girl is the human equivalent of the only high-end cashmere sweater that you did not buy on sale: dry clean only.
Care Complexity Level: 5.3 / 10
4. The Generic 30something Male
The more refined successor to the 20something Male, the Generic 30something Male has slightly more depth and emotional maturity but exponentially greater optionality. Because he has learned to pretend to listen and has the interest of not only people his age but also 20somethings, you must wage psychological warfare on both him and yourself to attract and keep him. This means ignoring him for long periods followed by lavishing affection on him in front of his friends and family to boost his still-gestating ego. If he ever says, “I’m busy,” never contact him again, and within 3 months he will ask you to marry him.
The Generic 30something Male is like traditional denim: relatively low maintenance if you follow instructions, but easy to shrink if you expose them to too much heat.
Care Complexity Level: 2.9 / 10
5. The 30something Finance Guy
After a hitting a 10-year-low in desirability in 2019, the 30something Finance Guy has steadily regained value in the marketplace as a result of soaring restaurant prices and the threat that AI will make every venture-backed tech startup totally worthless. While short on personality, the 30something Finance Guy works long enough hours for you to have a robust, independent social life underwritten by (in descending order of magnitude) hedge fund, private equity, and investment banking bonuses. The 30something Finance Guy is a great choice for what his industry would call a “personality hire:” a quirky, artsy, charmingly unreliable person with peculiar and fleeting hobbies. All you need to do to maintain the 30something Finance Guy is maintain your appearance.
The 30something Finance Guy is like the business suit that he wears: kind of drab but well-tailored, and you won’t wear it often enough to have to clean it—just steam it every once in a while to loosen it up.
Care Complexity Level: 3.6 / 10
6. The 30something Tech Bro
This variety of male requires similar care to the Generic 30something Male but believes that his value to you and the world will magically and stratospherically skyrocket within 3 to 10 years as a result of something called a liquidity event. This is when his cartoon wealth becomes actual wealth, and it will coincide with a conversation about his newfound interest in psychedelics, Burning Man, and having a lot of sex with people who are not you (aka polyamory). If you are content to one day have a relationship structured like a Hamptons share house, tell your 30something Tech Bro that you are proud that he is changing the world of vertical SaaS and support his efforts to do the work, like ketamine.
The 30something Tech Bro requires a similar amount of type of care as a special edition pair of sneakers: try not to scuff them up too much, and time will tell whether they will be worthless or a collectors item.
Care Complexity Level: 4.1 / 10
7. The 30something “Girl Boss”
The Girl Boss has dedicated her existence to work and achieved early and significant professional success. On the surface, care instructions for the Girl Boss will seem simple—maintenance varies only slightly by age, she has outsourced everything other than the demands of her job, and she has one preferred spot each for coffee, power lunches, boozy dinners, and late night cocktails. There really isn’t anything for you to do other than brace yourself and try to forget what affection feels like.
Like the 20something Female, there are only two types of Girl Bosses, but you will not know which type of Girl Boss you are dating until they put you on a performance improve plan (PIP), which is an indication that you have misjudged which type she is, and your relationship will terminate within 30 days. Your best approach to maintaining a relationship with a Girl Boss is to flip a coin and bank on her being one of the following:
a. The Girl Boss Who Secretly Wants an Alpha-Dom is like a leather saddle—she will be extremely stiff and void of character for quite some time, and it will take consistent force to make her supple. This variety of Girl Boss will never communicate her needs, because she is either not aware of them or lacks the emotional maturity to communicate them, because all of her energy has been channeled into projecting power, competence, and confidence. In order to maintain this variety of Girl Boss, you will need to project even greater power, competence, and confidence and show no trace of vulnerability, weakness, or emotion.
b. The Girl Boss Who Secretly Wants Warmth and Nurturing subconsciously understands that successful male-female relationships must have polarity, and given she inhabits the masculine, she is intuitively drawn to men who can inhabit the feminine. To care for this variety of Girl Boss, imagine she is Desi Arnaz and you are Lucille Ball: you exist to entertain and sooth her after a long day of absolutely crushing it. This type of Girl Boss is like a pair of Loro Piana cashmere jeans—she appears very tough, but she requires very delicate care.
Relationships with Girl Bosses have the highest failure rate of any romantic connection, as evidenced by Jennifer Lopez’s four divorces from men who were either total alpha-doms or total beta cucks. This is because Girl Bosses unpredictably long for warmth after too much time with alpha-doms and suddenly resent betas for being too soft, which makes successful longterm partnerships with men who do not have split personality disorder very unlikely.
Care Complexity Level: 9.2 / 10
8. The 30something Female Who’s Freaking Out
The moment a typical Female (who is not a Girl Boss) hits 30, she becomes Tom Cruise in Mission Impossible in her quest to rescue the image she had at age 25 of her 32-year-old self: married to a true partner with relatively near-term prospects of children. She will make a totally chill first impression, but by the end of your second date she will make it known that she is not interested in sport-fucking you for several months and then being ghosted, which is standard relationship protocol in larger dating marketplaces. If you wish to maintain a relationship with a 30something Female Who’s Freaking Out, just do what you tell her you’re going to do, and circumvent her 30something Female Friends (Who Are Also Freaking Out) tattling to her that they spotted your dating app profile by pausing all of your accounts after one of you has brushed your teeth at the other’s home three times.
Think of The 30something Female Who’s Freaking Out as wetsuit: easy to get into, very difficult to get out of.
Care Complexity Level: 6.5 / 10
9. The 40something Man-child
Also known as the Peter Pan, the 40something Man-child generally evolves from either the 30something Finance Guy or the 30something Tech Bro when they realize that their desirability and optionality increases with each passing year and each additional comma in their net worth. Care instructions for this variety of male are very similar to the 20something Male: they are accustomed to every person they date believing that they are the one who will compel them to become an adult by perfecting fitting into their life and catering to their every whim, so a more unique strategy is to treat him with ambivalence and casually mention that you are also dating a someone half his age “just for fun.” This will create an enormous degree of competitive rage, which he will channel into not only surfacing his abs but also not behaving like the total fuckboy he’s been his entire life.
The 40something Man-child is kind of like a cheap Halloween costume: wear it once, and then trash it.
Care Complexity Level: 1.5 / 10
10. The 40something “Late Bloomer”
“What’s wrong with him?” you asked yourself at the end of your first date. He’s handsome, smart, creative, charming, kind, and thoughtful and seems like he really wants to not die alone, but he’s still single after adult-dating for like 25 years. To distinguish between the 40something “Late Bloomer” and his evil counterpart, the 40something Man-child, ask him on your second date why he’s still single. If his two-hour monologue can be distilled down to needing time to figure out who he is, what he wants, and how he will make a dent in the universe, he is likely a 40something “Late Bloomer.” The downside of this variety of male is that he is old, but the upside is that the voice in his head that tells him he’s running out of time will compel him to try really hard not to fuck up his relationship with you if aren’t missing more than two limbs and are proficient in his native language. In love language parlance, he will require so, so many more words of affirmation than you are probably remotely comfortable with. Just tell him several times a day that he looks 10 years younger than even his fraudulent dating app age, and assure him that the men you have dated who are your age are insufferable.
The 40something “Late Bloomer” is like an expensive pair of dress shoes: a significant upfront investment that will break in and conform to you over time.
Care Complexity Level: 7.6 / 10
11. The 40something Independent Woman
The 40something Independent Woman is probably the single most powerful and compelling person in the dating marketplace. She has either made peace with not adhering to or rejected entirely the traditional romantic timeline and is focused on living her own best life. She often dates much younger men and treats them like foster dogs—with care but also with pragmatic detachment. Care instructions for the 40something Female are very simple: respect her time—because she has many different ways she can spend it—and add some fucking value.
The 40something Independent Woman is like a perfectly broken-in hoodie: perfect for any occasion and low maintenance.
Care Complexity Level: 3.2 / 10
12. Any Gender of Human Over 50
Humans typically run out of fucks by their 50th birthday, so this makes everyone at or north of this milestone capable of taking you or leaving you, which makes for a very chill vibe. They will know who they are, and they will appreciate whatever makes you special, because they have a statistically significant body count and know that you may be one of the last people they add to it.
A male or female person over 50 is like a leather jacket: zero maintenance, and it gets better with age until it falls apart.
Good luck with whatever person you’re dating, and try to follow their care instructions if you really like them.
Bravo. One of your best. So relatable, for anyone who's spent time dating in New York (or any of the other bougie locations you reference).