Why is dating so hard for guys?

This one’s for the guys. No, no, not the boys – the men. Why do I stress this? Because the boys will believe themselves to be wise in their own eyes, cower from shame and run (or raise a fist) at the hint of correction. If that’s already you four sentences in, I advise you don’t read this post. Real talk – you’re not ready for it.

This especially goes out to the men who hope or expect to *lead* (in relationships). You need to receive this message tenfold because the dead, cold, hard truth is if you want to be a true leader in relationships and marriage then you need to become a servant. Go ahead and bookmark that post for later.

Yeah, so? I’m a woman speaking on why dating is so hard for guys. Is that I have something to say a surprise, or is it simply that what I say will be impossible to believe? The same way women ought to consider a man’s perspective on dating and relationship advice, so should men.

I’ll tell you what I see so often and so heavily in our culture – the blind leading the blind. Have you ever thought to yourself that someone on the outside can see something you don’t, or something you continuously fail or refuse to see? A different perspective may be all it takes for someone to have an Ah-ha or lightbulb moment.

You might be thinking I’ll touch on things like smaller social circles, unrealistic expectations, higher competition (especially with online dating) or the fact that women are opting out (and instead in pursuit of that hyper-independent, don’t-need-no-man lifestyle). Sure, but I’m wanting to amplify the things spoken more quietly that need to be yelled to the men in the back. These are likely the things you won’t hear or be told among your fellow Redditers.

I ask that you listen closely before you read on or jump ahead – please – because I do not sugarcoat the subject. If you’re someone who has been asking, “Why is dating so hard for guys?“, you’re going to get an answer that won’t necessarily tickle the ears. Some of my answers (solutions) are not going to be as cut throat as anticipated, but I think solutions are also designed for the individual to fully unpack on their own in their own time.

The fact is nobody does dating perfect or right – even I, a happily married woman, didn’t have the oh-so-perfect dating experience. I was far from perfect. So the person who says they’re doing everything right or nothing wrong is a total fool.

Now then, how you receive my answers and what you do with them – that’s on you. But know this: if your initial reaction is to scoff, you might seriously want to question whether or not you are solely after what you *want* to hear versus what you *need* to hear.

Why is dating so hard for guys?

Why is dating so hard for guys? This one is for the men who have been struggling tirelessly with dating in hopes of finding a relationship, or the right relationship. As a woman, I'm giving you what you need to hear rather than what you probably want to hear.

The unexplained divide

From what I can see and gather, the graphic below depicts one of the two dating scenario struggles for men. *I made this graphic, not AI – thank you, thank you, you’re too kind.

So, which one are you? If you make it through and go on to read the rest of this post, you may start to wonder if it was better suited for the guy on the left. And maybe so, but I still think there are important tid-bits to gather even if you equate yourself as being the guy on the right.

While there’s validity to this graphic and the experiences are real, you still have to realize that there are a lot of people in relationships. There’s also lots of people dating successfully – again, you’re just not going to see those people taking it to Reddit. So, yes, obviously you will see a lot of the extreme sides of singlehood difficulty when it comes to dating but, IMO, I have a hard time fully believing it’s the greater “norm”.

On the flip side women would have a similar graphic, with there being a great divide, but it would look a little something like this:

Ah-ah, remember, while you may not be able to resonate with that graphic or you have your own opinions about it is not the point. The point is women have their own dating struggles, too. Whether or not these struggles represent the majority or average, that doesn’t mean they are fact or healthy (justified), but they can still be valid and real experiences.

So while I don’t have an exact solution or even a solid answer for this uncanny divide that seems prevalent in dating culture for men, I can still say that no matter which side of the cliff you’re on…you’re still individually responsible for yourself and how you allow the side you’re on to shape your attitude and outlook. Each side must be open to change when and where needed, overcome inevitable hurdles, learn and practice acceptance, and focus on personalized values and goals rather than what society, culture or whatever mainstream trends are tells you. And this looks different from person to person.

The reality here is that dating culture for men typically says:

  • You have to have a lot of dates to find a suitable partner
  • You’re a high value man or partner (desirable) if women are lining up to be with you
  • Unless you look like *this* and make *this much* money, women won’t even notice you
  • For men to find a suitable partner and gain relationship experience they need to “play the field”
  • Going on dates even if the person isn’t relationship-material is better than no date
  • If you’re not dating consistently you’re less likely to be in a relationship or find a partner
  • Men who aren’t seeking commitment or marriage should still date (date for hookups), otherwise they are losers/loners/less of a man.
  • There’s something wrong with you if you haven’t been on a date in X months/years since your last relationship
  • Men who don’t date chronically or consistently are weak and will miss out on companionship

For one thing, if I’m being honest, it seems as if the takeaway message here is that we ought to reshape our thinking on dating abundance. Since a lot of men will say women have exponentially more dating options and opportunities than men, which I do agree with, I actually think there could something to that. Meaning, it might actually be unhealthy – for both men and women – to treat dating abundantly. Or to fill our plates to the brim, basically.

For men, it’s possible that they may be operating in a scarcity mindset which makes them behave in ways that are the opposite, such as the guy who will quite literally date anything that walks.

Think about it, scarcity tells us one thing while abundance (or prosperity) tells us to never settle, fill your plate (whatever you don’t like or finish just toss aside) and to test drive before you buy.

Those things can create their own difficulties in dating because you’re conditioning yourself to the opposite of commitment and all it entails. But if we were to do away with depravity and glut, we might focus on getting to know fewer people better, deeper and on a level that prioritizes partnership compatibility rather than aimlessly dating superficially and materialistically with no real meaningful direction or purpose.

I thought this is what online dating was set out to do, and I believe it can and has accomplished that, but I also can’t unsee its opposite effect and damage it has done that only seems to highlight this very divide. If you’re interested in opening up more on this subject, I’d be happy to – just leave a comment or reach out.

There’s always an excuse to blame, and it shows

Dating is obviously difficult when so much energy is spent casting blame, especially when it’s on the other side (women). I see it non-fricken-stop. And don’t think for a second I am somehow condoning or writing off everything women do, or that women do not partake in the same nonsense – take that level of emotional immaturity out with the trash.

Everyone, and I mean EVERYONE has been burned by crappy people on crappy dates and in crappy relationships. So when the focus is more on women (who she is, what she’s doing and not doing) and less on the kind of man and partner you want and strive to be (even if you meet the wrong person), you’re inevitably doing yourself a disservice and risking turning off and away possibilities that come your way.

I also see, one after the other, the number of guys literally calling themselves short, fat, ugly (all the things) and that is to blame for their dating unfairness or inadequacy. As if somehow THAT attitude alone will even remotely be attractive?? I’m just saying, on a regular basis I notice real couples in the real world that dated straight out of each other’s league. And not to say that’s a bad thing, but to prove that attractiveness is subjective and that looks are not everything.

I know this one isn’t necessarily going to satisfy as an answer to a long-time, on-going question for guys, yet it’s an answer that needs saying because I believe the point is often missed.

Notice where I said it shows? That’s because it can, and it does. When this molds and shapes your lifestyle (i.e., “women turn me to drink”), identity (i.e., “women made me become an a**hole”), attitude, confidence, tone, reactions, responses and ultimately your behavior it can absolutely come off as arrogant, miserable, undesirable and unstable.

Looking for a long-term partner playing short-term games

So, you don’t think this is possible? The number of guys I notice who will talk up the woman they’re seeing based on a number of things (usually superficial) yet admit they don’t see fit as a long-term thing…and keep seeing them!

Or they will completely wash the one, major thing they’re seeking in a partner for the sake of looks, sex and a good time (short-term companionship).

Better yet, they’ll engage with someone completely wrong for them for the sake of this person fitting the description of their type physically.

I say this to women the same, stop entertaining those who only bend your rod but don’t fit the description long-term. Stop engaging in short-term games with the intent for a long-term partner. You have to get off the carousel since that ride will only keep going around and around, and won’t stop, until you get off.

Stop dating women you wouldn’t marry or bring home to meet mom.

Psst, reads you also may like..

If she wants to get sexual or sleep with you on the first date (or early on), you’re not that special

Come at me all you want – a guy will usually have less respect for a woman (as a dating and relationship prospect) who sleeps with him early on (or on a first date). Hey, the same way I would lose respect for a guy who wanted or tried to get it in early on or on a first date.

Here’s the thing that mind boggles me: guys who are totally cool with and open to sleeping with her on a first date (or early on in dating) yet slap a label on that woman and, coincidentally, claim they are tired of dating *easy* women.

I’m going to, hopefully, enlighten the guys for a second here in saying that not only is she not that special to you (if you’re sleeping with her on a first date or early on) but that YOU’RE not that special, either. In saying that, sex itself is no longer special or sacred – it’s equated to a basic human function or part of the mundane being checked off a list.

[Related Read: Has Hookup Culture replaced Dating Culture?]

So, yeah, when you factor these things all together…dating is difficult. Dating is difficult when you refuse to assign a higher value to something that is blanketly treated like a regular Saturday night out. Worse off is doing this same thing over and over and expecting a different outcome. These are the guys who expect a hoe to magically become a housewife. Look, I didn’t say it – take that one up with Dr. Dre. Again, I apply the same logic to women: you can’t make a man-whore magically turn into the man of your dreams.

For the men who are truly looking for a relationship and a long-term partner, I think that is going to hit where it needs to, otherwise the rest are just going to continue saying, “But I got needs,“, “Yeah, but in the end I still got some,“, or “She was willing to give it up, and I’m not going to turn down the opportunity.

The way of the fool is folly, that’s all I can say there.

Unreasonable, unrealistic expectations disguised as preferences

I am not saying I am against preferences, but I do think preferences have overwritten shallowness. While men continuously feel height and stature (physique – the six pack) are their constant losing battle with women’s expectations, or preferences, let’s not act like men aren’t playing their own version of this game.

Men are just as guilty of sidelining the right person simply over certain outrageous and unrealistic physical features not matching their *preferences*.

Here’s where I’m going you’re likely not expecting. Unfortunately, p*rn, the over-sexualization of physical features, our culture’s standard of beauty and the emphasis on anti-aging has done one hell of a number on what we find not just *attractive* in general but what is hyper-sexually desirable altogether. IMO (I don’t care, disagree with me all you want), these have done irrefutable and possibly irreversible damage.

Dating is incredibly hard when superficial, physical preferences are higher on the totem pole over the qualities in a partner that actually matter long-term when looks falter, change, fade, and evolve *naturally* with age.

Is the competition really with other men, or is it with her?

Seriously! Are men truly competing with other men, or has the game done a complete 180? I ask this because I’m noticing the amount of men who seem to get butthurt over the idea of an elevated woman. That it’s somehow emasculating if she… makes more money (than you), has a “better”, more highly educated or skilled career (than you), happens to spend quite the dollar amount of time and effort on her appearance and lifestyle, portrays a “standard” in a partner who can level with that, and the like.

I know the immediate response will probably be something like, “She won’t even glance a guy’s way if [1] he doesn’t make just as much or more money than her, [2] he doesn’t have an equally successful career or the same level of prestigiousness as her or [3] he won’t cater to or can’t keep up with her spending lifestyle.

While I’m not denying this happens – really, I’m not – I do have to question and wonder if that’s totally accurate in every circumstance. Honestly, do men expect a 30-something year old single woman to wait around *helplessly* and purposelessly in life for a relationship (a man) to fulfill those things? A woman who happens to be successful in life before you or without a relationship doesn’t change the fact she’s looking for a partner.

And, yet, I understand that it is hard when a woman who makes 6-figures wants a partner to meet or exceed that. But it’s no different from women who are more old fashioned and value a partner that is capable of being the financial provider.

I can see where that sounds like, “You’re worth what you do, make or bring to the table.” There are certainly perfect examples of this on both sides of the coin, since not all value is monetary. Unfortunately, people care too much about net worth and put too much value on the dollar amount when it comes to stability, equality in partnership, and life success. And my only input here is that financial compatibility is underrated and not considered enough in dating.

Go bold or go home with your tail between your legs

Shy, quiet, and even the more out-going, confident guys – you’re all included here, so listen up! There’s one thing that will never change, and that’s that men and women like being approached and flirted with appropriately (not creepily), so let’s not pretend otherwise.

Here’s what I’m finding: fewer guys are approaching women, initiating the first move, or making bold moves. The top reasoning? Well, apparently, it’s not worth it or there’s nothing in it for them without a return.

Um, wait, hold up. It’s not worth the…what…rejection? There’s the dog with his tail between his legs. In this life, rejection is inevitable and ratification isn’t promised. Plus, the more you date and the more people you date the greater risk of rejection.

What am I getting at here? Am I saying that more guys are increasingly sensitive to rejection, and therefore avoid any and all possibility of it? Potentially, but have guys forgotten that women get rejected, too? It’s a sucker punch to the gut to be ghosted or told you’re not interested conveniently after touching body parts. The thing is, your worst nightmare is already your reality. The worst thing that could happen is she rejects you, and you’re alone, which is your current state.

Guys who are saying screw it to initiation or to putting themselves out there are losing every single shot they don’t take, and yet are going to keep coasting on the wave of past and possible rejection as if that will somehow make them feel better or, better yet, make women *step up* their A-game. It’s really not the “Gotcha” you think it is, it makes you unapproachable.

I’ve said to the ladies and I never thought I’ve had to stress it to the guys – stop taking rejection so profoundly personal when it’s a blessing (the blessing of your time not being wasted over someone who isn’t for you).


Now that’ve you made it to the end, my dudes, tell me what you think. Did you learn anything new? Even if I’ve heard it a million times – why is dating particularly difficult for you?

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