Late 20s is the worst age range of people to date

Enter scene. Two men are seated on a bench in a moving NYC subway car.

Kareem: So what’s your take?

Amogh: If you live in a big city, the absolute worst age range of people to date is late 20s.

Kareem: 100% agree! But tell me more . . .

Sadly, I’m not a famous enough influencer to actually get on an episode of SubwayTakes. But this is Amogh’s Hot Takes! I don’t need to wait for my chance at stardom! I’ve already got 69 whole subscribers! ¹

My villain origin story

In early 2023, I decided to get more serious about my dating life. I was a hesistator—which is a dating tendency I read about in “How to Not Die Alone.” Hesitators always have an excuse for why they’re not ready to date. I had just turned 28 and had only been on dozen or so dates in my adult life. I had received some recommendations for dating books and decided to finally dig in.

I wish I had read these books 10 years prior. Every other sentence was revelatory. The points discussed echoed and explained my many failed attempts at dating over the years. Now enlightened, I have some understanding on how to play the game.

I continued reading dating books while fighting my hesitator tendencies. Over the course of the year, I went on dates with 18 different women. As I continued to date and read, my insecurity about being an inexperienced dater fell away to a new revelation: I know more about dating than most people; and certainly more than the people I was dating.

Modern dating is new

From reading Modern Romance, I learned that the current era of dating is very new. Previously, people would meet their partners very young—they likely lived in the same building or went to the same church. Couples tended to marry young and fairly quickly before going on to build a life together—not so dissimilar from an arranged marriage.

In contrast, people now build their own life and career before prioritizing finding a partner. In bigger cities especially, marriage often doesn’t happen before the age of 30. The modern world of dating is incredibly new. But few people know this history.

The Dunning-Kruger effect

Most people assume that we are born knowing how to date. From this assumption comes a classic Dunning-Kruger effect. Most adults are blindly confident in their dating strategy. Even worse is when they give bad dating advice to their friends!

Perhaps this dynamic isn’t all bad though. What would people talk about with their friends if not bad dating advice? Brunch spots and bars would go out of business. We never would have had Sex and the City!

But I do think all single adults have a responsibility to pick up a book and learn how to date properly. Next week, I’ll share my famed dating advice presentation and recommended reading list, so be sure to subscribe.

Give people a chance, stop maximizing

The one peice of dating advice that every reputable dating book echos is to give people a chance. Too often, my dating experiences in New York have ended after 1-2 perfectly fine dates. Nothing had gone badly on these dates; the explanation was often that they just didn’t feel a spark or a romantic connection.

But neither did I! I was just trying to follow the advice from dating books and give chemistry a chance to develop. I have a pleasant enough time on most first dates so my default response is to try again.

Living in a big city, there is an abundance of single people. I also have a hypothesis that ambitious and driven people who come to big cities tend to be maximizers.

A maximizer tendency—the instinct to always find the best option—is counter-productive to finding a partner. Because unlike blenders on Amazon or the top 5 NYC pizza spots, there simply isn’t an objective best. Every person will have many good qualities and some bad ones. But it will be hard to find the good if prospective partners are quickly dismissed.

My hot take

Which brings me back to my hot take. People in their early 20s are just trying to figure things out. They might get into a relationship, they might not. It’s just too chaotic of a time. But if you are still dating into your late 20s and haven’t found a partner, odds are that you’re a maximizer that hasn’t learned to give your dates a chance. And by 30s, most people have wisened up. They have learned the hard way that it’s time to expand their perspective.

It’s possible to shift your mindset

A few months ago, I was telling a few friends about how I had unsuccessfully asked out someone in person. My friend Erin was surprised by this. Her response: “What was the alternative? Why wouldn’t she give it a shot?”

I doubt Erin even remembers saying this to me but I was astounded by this response. This is not at all the mentality of the average single person in NYC! Erin’s perspective on dating is to be default inclusive; the opposite of a maximizer. This makes a lot of sense, Erin has been married for 10 years.

Even if you are in your late 20s, you are not doomed. It is always possible to shift your mindset. I encourage you to think more like my friend Erin.

¹ I am not choosing this number to be funny, this is actually my subscriber count at the time of writing publishing this post.