Men Discuss the Biggest Obstacles to Dating Women Today

September 22, 2023

Dating can be challenging for both men and women in the modern world. With the rise of dating apps and shifting gender norms, the dating landscape looks much different than it did even a decade ago.

To get an inside look at some of the struggles men face when dating today we took a look at the biggest struggle with dating women nowadays?

Getting Matches and Setting up Dates is Difficult

One of the most common struggles mentioned is simply getting matches and first dates with women in the first place. For many men, this initial hurdle of making a connection is the hardest part.

As one Reddit user put it:

"Getting a match online. Meeting women in my friends circle who are single. The first hurdle essentially!"

With so many dating options available through apps and websites, it can feel like an uphill battle to stand out and make a real connection. Men reported feeling like they are competing for women's attention against countless other guys in her inbox.

"I feel because of social media and online dating the game is stacked wayyy too much against us. Us dudes are fighting an uphill battle vying for attention when she can open an app and talk to any of the dozens of dudes in her DM's."

Trying to meet women offline comes with challenges as well, from hectic work schedules to limited social circles. Taking the initiative to approach women in public places also comes with the risk of being perceived as creepy or inappropriate.

Women are Perceived as Flaky and Non-Committal

Another common frustration expressed is women appearing interested at first but then seeming non-committal or flaky when it comes to making concrete plans.

One man described it as:

"Rampant flakiness. Going on a few dates, seem to be hitting it off, set up plans for another, then get told something along the lines of "you're great, but I'm too busy to date right now"

Some men feel like women are keeping their options open and not truly interested, even when things seem to be going well. There is a fear of being strung along or treated like "just another option" rather than a priority.

Double Standards Around Initiating Interest

Several comments touched on frustrations around women expecting men to initiate all interest and courtship.

As one user put it:

"The never-ending feeling of being in a race against time during the dating phase, where the line between "too soon", "too late" and "right on time" seems always blurred."

Another commented:

"When we are always expected to make the first move."

Men reported feeling pressure to drive all conversation, come up with date ideas, and pursue the woman while she waits passively. If they don't make a move fast enough, they risk getting friend-zoned or having the woman lose interest. However, being too forward risks making women uncomfortable or getting labeled "creepy." It's a delicate line to walk.

Finding a Genuine Connection

At the heart of it, many men's dating struggles seem to come back to making a real interpersonal connection amid all the noise.

One man summed it up as:

"Knowing if a woman is genuinely interested or just being nice. I am currently experiencing it and it's a pain."

In a dating environment full of mixed signals, ghosting, and keeping options open, men reported difficulty discerning when a woman is truly interested in dating seriously versus just being friendly or seeking attention/validation.


While dating challenges are certainly not exclusive to men, hearing their perspectives shows some consistent pain points:

  • Standing out and getting initial interest can be difficult amid many competing options
  • Women sometimes appear interested but then non-committal when it comes to relationship progression
  • Men feel pressure to always initiate pursuit and "impress" the woman
  • Determining genuine interest vs. flakiness is a constant struggle

The common thread seems to be a desire for less games, more direct communication and a real connection. By being upfront and intentional in their dating approaches, both men and women can improve the experience.

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