tldr of dating in your 20s: the mechanics and culture of modern dating (NYC-focused)
Dating as a call option, metagaming is a bad strategy, and other red pills.
Written from the male perspective (early 20s) from a professional background who has been living in NYC over the past year. Read, but not endorsed, by professional males and females who are actively or have recently lived in NYC.
The purpose of this document is to codify some of the third-rail intricacies and insights of modern dating.
Much of the modern dating discourse comes from downstream boomers and millennials. I’m here to tell you the cold, hard truth of dating mechanics as a participant and primary source.
To be clear, this piece should be interpreted as a meta-analysis. One does not have to agree with the following to understand that consensus behavioral expectations exist. I do not endorse or agree with many of these cultural norms – I am simply pointing out that they exist.
You might think this whole mating ritual song and dance is ridiculous. But there are many evolutionary reasons why it exists. It’s a better equilibrium than what has existed in the past when men would literally duel or fight a war over a girl.
I would hate it if the takeaway of this post is that people view dating from the perspective of an EA utility-maximizing extremist and further perpetuate what I think is an already suboptimal dating culture. Life is an experience to be enjoyed. Talking and having sex with a truly compatible partner elevates all aspects of life. Evolution has correctly aligned these incentives.
A healthy amount of skepticism should be considered when reading this – don’t overfit your conception of dating to any particular model.
The earlier you’re able to internalize the following and swallow these universal truths, the quicker you’ll get up to speed with the current culture (or at least be less frustrated). The game is what the game is, don’t be naive and think that any single person can change this.
Dating is a market. Online marketplaces made this much more apparent and efficient, with unprecedented access and freedom to communicate among individuals. Standard power law rule applies (a small percentage of the market reaps outsized rewards).
Competitive dating markets have similar dynamics to talent markets. It is helpful to view a potential relationship as a call option (a call option is a financial instrument that gives you a significant reward if things go well). The desirable individuals from both sexes are inundated with messages. Because of this, you as a suitor want high variance in these messages to elicit a response.
An option is worth more if the underlying asset is more volatile, though there are some practical limitations to this in dating. In dating, girls genuinely have different preferences here (they implicitly understand the tradeoffs of dating a hyper-successful maniac such as Elon). The reality is that there are much fewer trade-offs than one might imagine in a career in tech – founders are often paid the most, have the most equity, and can “fail up”.
In your 20s, it is helpful to think of guys as the fledgling startups and the girls as the VCs. Girls, especially in their early 20s, subscribe to the notion that their perfect guy is out there (to be fair this is a fair strategy for a portion of females). You must convey yourself as someone with the potential to be 2 standard deviations better than her mean to even have the chance to meet her in person.
Metagaming (trying to signal that you are above dating culture in some respect) might feel like a 200 IQ cheat code, but it just reveals you to be an amateur and unserious person. This is a negative EV strategy.
Metagaming is appropriate with very trusted family members and friends (usually in a non-dating context). Achieving this level of trust is a very hard bar to clear. I would use 1 year with a non-referenced individual and 4-6 months with a referenced individual as a baseline, unless you think you’re a very good identifier of talent (hint: you’re not).
City dynamics matter. A city with 46% men and 54% women might not seem like a big difference, but it is. It translates to 17.4% more women than men. In a place like NYC, this means 10,000+ women without a partner. The inverse is reflexively true in places such as SF.
Even people you might consider 1.5-2 standard deviations to the left of you are fuckable. The market overvalues looks – this can be used to your advantage. Love can emerge from unexpected origins.
The person you think you have a connection to has a roster – you aren’t the only person they’re talking to.
Girls espouse feminism as a group but act as rational participants in the dating market by maximally extracting and optimizing for their personal welfare. Guys are less covert about this but have the same incentives.
Asking a girl out on a date really isn’t that big of a deal, especially in a city like NYC.
People in general really hate saying no to things. People will go out of their way to not say no.
If it’s a trusted friend or someone else you have a rapport with, it can still be done tastefully. There’s no catch-all advice here since it will be context-dependent.
Giving up is cope. Take breaks and prioritize other aspects of your life, but finding your life partner is a very productive catalyst for all other aspects of your life so don’t think of it as an isolated duty to be fulfilled.
Adverse selection definitely exists in online dating markets, but it is less pronounced than you might think. Adverse selection here refers to the fact that the best potential mates are either already in relationships or have a strong, offline social circle of candidates to source from.
There’s much more cultural acceptance for online dating and is becoming the default, so I wouldn’t worry about this too much. You might not find Sydney Sweeney or Livvy Dunne on Hinge, but you aren’t even the same species as them anyway.
For all intents and purposes, Hinge is currently the major league. Most of one’s online effort should be allocated accordingly.
Some ground truths:
The first iteration of your profile is hot garbage.
Signal for what you want.
Many helpful guides exist online as to what pictures signal in the modern dating market.
High-quality pictures with your face and body, no group photos where it’s unclear who you are, and no car photos probably put you 1+ standard deviation above the mean
e.g. Shirtless profiles signal a fuckboy mentality
Good, thoughtful responses to prompts are underrated and signal to the market that you are witty and can likely hold down some semblance of a conversation.
Guys should always have their profile as “LTR” on Hinge if public (and it should be).
You must have this set as “LTR” as a guy to not be categorized as a fuckboy. Girls can get away with “LTR, but open to a short-term relationship”. Anything else is trashy and/or non-serious.
Use Tinder if you’re desperate for a hookup. Just know that Tinder is a cesspool so proceed with caution.
Improvements at the margin:
all lowercase letters and messages are often seen as tasteful. i would be curious to know what the cultural evolution of this was, but i assume it demonstrates some form of non-chalantness that captures us zoomers.
Good culturally engaging humor and references are underrated.
For the crypto bros out there: take crypto out of your profile, whether you own or work in crypto. You can tastefully tell her you work in crypto on the first date, but you’ll forever be fighting uphill as people (correctly) associate crypto with scams.
No, you don’t actually know how the algorithm works but you can surmise general heuristics based on usage.
No, you’re not shadowbanned. Your dating profile sucks and/or you should spend your time improving yourself on some dimension(s).
Blaming the algorithm is 100% cope.
You should buy premium at least for a week if you’re in a large city. It necessarily increases your long-term equilibrium number of matches (lots of churn).
Having a verifiable source-of-truth for an algorithm would actually be pretty cool. We might have the first use case for zk + crypto.
You’re probably not 2+ standard deviations in attractiveness otherwise you wouldn’t be reading this. You have to earn your way via other means. In the context of online dating, this is via responses to their profile.
Say something specific and witty; again, think of this as a call option. The worst thing you can do is to be stuck in 0-match purgatory by writing mediocre, predictable comments that every single other guy is writing. It’s a much better strategy to go for something riskier using some piece of information on their profile.
You’re probably ahead of 95% of guys if you spend > 10 seconds reading their profile, using your brain, and not being retarded. ChatGPT can help with puns.
Geoguesser (“Guess where this photo was taken”) is becoming increasingly common. Many are hard, if not impossible. Better to shoot for the moon – even if you get it wrong, she’s likely going to respond if she likes you in the first place. If she didn’t like you previously and either your answer is correct or is otherwise funny, she’s much more likely to respond.
Keep it short and sweet. Fragmented sentences are accepted and oftentimes preferred. Reciprocate similar messaging lengths – one-sided texting can distort the relationship early before it even begins. Keeping an aura of mystery until the first actual in-person meeting is key. You want to seem like you have a life outside of texting her.
Don’t ask for the girl’s number, you can tastefully drop yours in the chat if you think things are going well.
Just ask for a date. If you’re not giving off red flags, everything you say or do is incredibly marginal. She’s already matched with you so the odds are very good she’ll say yes.
As mentioned before, girls can be best modeled as VCs. They get a lot of inbound (likes) and are trying to filter based on some signal (photos, background, prompt answers, etc.).
To get a sense of the differences in experience, the following are anonymized excerpts of the experiences of women in NYC.
Over 100 likes per week (professional, attractive girls).
50% are just a like, no text
35% have some vague, zero effort wording or an otherwise inappropriate wording
10% are decently creative
5% are elite
She’ll match with about 15-20 guys and talk to 6-7 per week
She likely goes on 1-2 dates per week.
Girls really care about the man’s height (oftentimes a hard filter), job, and degree/school.
Girls are much more forgiving on looks than you might expect.
Girls generally appreciate subtle, classy signals that you have some wealth.
First date. You made it. All courtship done previously doesn’t matter. You both will throw out almost all of the conceptions made over text. Your personality, past accomplishments, and visual appearance are all that matter during this date. Not to psych you out, but like YC interviews, she’s making a judgment within the first 5 minutes and spending the rest of the date confirming her priors.
Where
Not sitting across from each other is probably preferable for a first date unless you are confident.
When
Saturday late afternoon/evening is prime time. Scheduling for this time is the goal and gives you a signal that you are at least somewhat worthwhile from the other person’s perspective.
Friday is second-best.
Other weekdays are fine as well, depending on work and other schedules.
Attire
Aesthetics matter.
Clean, unbranded clothes cover all the bases for a good first date. You want to look put together. Ask yourself if you think she would be comfortable bringing you to meet her friends and family for the first time.
Add some flare if you know what you’re doing and have taste.
Interacting + Talking
Yeah, you have to talk on the date. This is too context-dependent but the tldr here is don’t be retarded. Just talk like you normally do and it’ll be fine.
If you’re really creative, you can see if she mimics your body posture and signals. This is one indication that she is into the conversation.
Most of the time, you don’t want to ask for a second date on the first date unless you’re 100% sure she’ll say yes. It just makes it really awkward for everyone. She’ll end up giving a nondescript answer in person and ghosting you in all likelihood.
Paying
If the guy really likes the girl and the girl really likes the guy, he’ll pay and she’ll let him. This keeps the door open for future dates where the girl can plan/buy other things and the guy will let her. It doesn’t have to be 1:1 in dollar value but just has to demonstrate genuine willingness from both sides. This is a pretty good equilibrium in my opinion.
Understand that you may very well be getting played for a free meal. False positives are normal and to be expected. Chalk it up to a cheap call option that went to 0. People systematically undervalue their time; the other person sucks for doing this but you’ll live. This behavior is punished in the long term.
Ending the date
Post-date messaging
Message her when she should have gotten home; girls absolutely dig this. It signals that you are thoughtful enough to at least signal that you care about her safety.
If you like her and want to see her again, shoot your shot, ask for a second date. Do it confidently and don’t be torn when she says she didn’t feel the spark. Again, options go to 0 all the time.
What do you do when the girl is clearly out of your league?
You talk, you kiss, you have sex, maybe you even have some inside jokes at this point. Maybe you even go super crazy and hold each other’s hand in public. Enjoy these moments.
There’s not that much to say here that’s generalizable because this is relationship-dependent and each person’s comfort level and preferences varies.
At some point, you reach a crossroads. You either end things, continue on as FWB (adding each other to your roster), or go exclusive.
In all seriousness, if there is a connection, go for it. This is what life is about – putting it all out on the line and seeing where the chips fall.
You FaceTime every night at 10 pm right before bed (10 pm Eastern/7 pm Pacific for you SF/NY long-distance couples). You confidently hold each other’s hands in public. You introduce them to your friends and maybe even your family. You start calling each other pookie.
Both parties will always wonder if they’re settling. On the streets of NYC, there’s always someone hotter, richer, more put together (New York especially values power and money).
You end up either having the relationship naturally drift off as one or both of you seek a better mate. Or you get married.
Additional thoughts and interesting related facts to keep in mind:
One structural problem with the dating market is that the most influential individuals are the people still on the market, which creates an adverse incentive. This is in contrast to typical markets where good producers are rewarded with a positive feedback loop and typically increase their market share and position. Good producers in the dating market are, by definition, off the market.
Each incremental sibling a person has reduces their divorce rate by 2%. Lust wears off and compatibility pivots towards being based on verbal and personality compatibility.
Contraceptive technologies and their second-order effects are very underrated. I expect to see contraception go beyond “wear a plastic bag over your thing” in the near future. TBD on how this affects the dating culture and market.
Dating apps have fundamentally changed market dynamics and led us to the current equilibrium of hookup culture. I have seen no cultural signs of this changing anytime soon.
I’m bullish on situations where someone (i.e. a trusted third party) expends social capital to mediate a relationship. This starts the relationship off on a different footing. Expect mediated dating and marriages to make a comeback over the next decade.
Some public intellectuals have said good things about finding a partner at a young age and being able to focus on other things. I can’t speak to the veracity of their statements but they overall seem genuine. You are reclaiming a lot of time and mental energy to expend on other things. Anecdotally, family friends who have gotten married early and risen the status hierarchy together are among the happiest and most content people I know at age 50+.
More context on how options theory applies to the dating market:
An option is worth less the closer you get to the date of maturity (the date on which the option can be exercised). In other words, the older you are, the more potential you are expected to have realized (financial capital, social capital, etc.). You are given more leeway as a younger individual, all things equal, because you have more time.
The people on your roster (conversely, you on someone else’s roster) can be construed as an internship or “trial period”. You are gauging the value of these options based on some interactions and other sources of signal. If you choose, you can make her a return offer.
Parents are incentivized for you to “settle down” early because they hold the opposite of an option from you (in addition to obvious selfish practical reasons such as having grandchildren). Parents act as insurance without any of the upside of additional volatility (having sex with hotter, more successful girls and the associated adrenaline). It’s no surprise why children of immigrants are more inclined to settle down earlier.
Certain, more conservative cultures such as Asian cultures value low volatility as insurance against all possible negative outcomes. When in your early 20s, it’s rational for girls to select higher volatility mates. In their late 20s, it’s rational for girls to select lower volatility and high expected value mates (that have evidence of some realized value). This is clearly one factor in explaining why cultures of higher risk tolerance do much better when younger, especially when compounded with evolutionary/innate reasons.
Options go to 0 all the time – you only have to be right once to be set up for life. ❤️