Why is Dating So Hard?

May 21, 2021

In 2020, I conducted a series of interviews with 20 people who were single at the time in order to get a sense of their biggest challenges with dating.

Because of the COVID-19 pandemic, all dating activity shifted to the dating apps. Many people didn't like this because they feel they have better chances in person, Three of the people in the interview series weren't currently active on the dating apps.

At a general level, both men and women were extremely tired of the whole process of dating online, and many of them expressed how similar the dating process is a lot like hunting for a job.

In fact, there's a lot of anxiety experienced around dating. They never know why they weren't selected or got no reply to messages, looking for a job can feel like a full time job in of itself, and once they start talking to someone it can feel like a job interview. One mistake and they're out—the other person will have moved on to the next candidate in line and they often don't even get a reason; they're just ghosted.

This can be incredibly frustrating and depressing, so it's no surprise that people often give up or take extended breaks off the dating apps.

Dating App Technology is Both Good and Bad

In the previous generations, people were mostly limited to proximity of who they met in-person or who they were introduced to through the people they already knew.

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With the advent of the dating apps and online dating sites, the world really opened up in terms of dating choices. Heck, you could even meet people in different countries if you know you're going to be traveling! But that very fact of having so many choices is what causes people to give up on potential people much more quickly. Many people have admitted that they feel there are always more choices to be had if things don't work out with the current date, so they think it's easier to quit and move on versus working out any issues with their current person.

This is why both men and women felt like they couldn't afford to make any mistakes ever, because the fear is that their date will ghost them and just move on to the next person in line.

They also expressed how transactional the dating apps felt, and that the level of connection to be had with the people on them was more than 90% superficial.

Why People Think They're Still Single

This is where the answers got pretty interesting, because there were drastic difference between how men think versus how women think.

What men believe is holding them back from finding a partner:

  • that they need to be a 9/10 or 10/10 on being good looking
  • they have to be over 6 feet tall
  • they should be making over 6 figures
  • they have to drive a nice car
  • women hold all the power on the dating apps, and an average looking women has plenty of choices but an average looking guy has zero to few choices

What women believe is holding them back from finding a partner:

  • they have a certain type they're attracted to, and people outside of that type simply don't work
  • dating takes more time and effort than they're willing to give, but they're confident that they would be successful if they did put in the effort
  • being over 30 means they're too old and men want women still in their 20s
  • they're not pretty enough
  • men aren't willing to commit and just want hookups

When asked, "if you could wave a magic wand, what would change about your dating life?"

  • Men: I would find my forever person now or very soon and get married
  • Women: I would like more candidates to choose from online

What's particularly interesting about this response from women is that in the United States, dating app usage on Tinder is roughly split at 70% men and 30% women, and Bumble being similar at 67% male users. a This means that a typical, normal woman easily gets five to more than a dozen matches per day, whereas a normal guy might get one match per week.

What Really Holds People Back on the Dating Apps

I currently do dating profile audits for people, where the session is all about how to get their profiles up to par so that they can attract more of the right kind of people. The biggest problems are almost always around having quality photos, and then putting in the right kind of content into their profile.

Any dating profile should offer this information, at a bare minimum:

  • what kind of person you're looking for
  • your values, or what's important to you
  • a description of your personality, and how you like to spend your time
  • clear expectations on certain issues, like whether you want kids or not
  • good quality photos that are a mix of close up and farther away

Essentially, creating a good dating profile is a lot like a marketing exercise: think about the kind of person you want to end up. What kind of personality should they have, ideally? What do they like? What kind of lifestyle and values do they have?

When you have this kind of picture of that person in your mind—keep in mind that this has nothing to do with their looks—you'll next think about what qualities about YOU that such a person would probably be attracted to. These are the qualities that you should be writing about in your dating profile. Constructing your dating profile is essentially a practice in working backwards from that ideal person and laying out a trail that will catch such a person's eye and lead them back to you.

The biggest mistakes people are making in dating

Now, even if you have a great dating profile set up, that only means you'll be getting noticed. People will start to contact you. Once you've got the messages open, what will you do next?

Here's what trips people up the most:

  • only thinking about what they don't want, instead of the kind of partner they DO want
  • talking about previous relationships too much
  • thinking that everyone is out to take advantage of them
  • interpreting or assuming the other person's motives or what they're thinking
  • lying about their career, income, appearance, past history, etc.
  • refusing to accept that someone is just not that into them or otherwise ignoring direct, verbal statements that the person isn't looking for a relationship
  • thinking that their choices are limited and they have to settle
  • being overly picky or holding on to a huge list of unrealistic expectations
  • they don't know how to open a conversation in a way that's remotely interesting


Dating in today's world is definitely a tricky experience that can be quite stressful. No one likes to feel hurt or rejected, and it often seems like that people are in such a hurry to avoid being dumped that they choose to do things they normally wouldn't. But what people often forget is that everyone is in the same boat: dating online isn't easy for anybody, and everyone is feeling at least a little awkward some of the time.

If we could give each other the benefit of the doubt, learn to accept that not everyone is going to be the right fit for us and express that honestly without judgment and without ghosting, how much better would the dating world be?

It just has to start somewhere with each of us choosing to believe the best about other people, being honest about what they want or don't want, and practicing kindness.

It can be done.

The life you want is waiting for you.

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