10 Reasons Dating is Hard in 2021!

Trey Hamilton
17 min readJan 25, 2021

Ah, dating 10 years ago. If you liked someone guess what you did.

You told them.

Here’s where it gets exciting. If they liked you there would be no games, no “low key feeling you”. They would just come out and say it. Imagine that.

But these days, dating is an explosion of misinterpretations, mixed signals, transactional bodily vices, and an overwhelming amount of options. Because of this dating has become a little harder to wade through and only the strong survive. But in this brand new decade, why is dating so hard? What are some things that hold us back, and what do we have to deal with? Here are 10 reasons why!

1. People don’t break up, they ghost.

Human beings are like water they’ll always take the easy path of least resistance. Because of this rather than acting like an adult and having a real conversation they run away from their problems and make memes about “adulting”. Rather than actually, ya know…

Be an adult.

Imagine if you were trying to have a conversation with someone you were actually dating face to face. Rather than have a response to your question they ignored you. You try and try and get them to respond but still, they’d ignore you. You’d think that person was bloody crazy! But because it’s an Online Dating App or text. We somehow have the gumption to ignore them when we’re not face to face. The more faceless the communication the easier it is to cower and ignore a key issue you refuse to deal with. But this is commonplace with people who ghost. Imagine how many potential dating scenarios could have been saved if they only communicated rather than vanishing into thin air. This right now is a dating epidemic and no one is safe!

2. Let’s talk about sex baby! (We’re just tryna’ smash)

Some people are just trying to get their rocks off. It’s not just men either. Women are interested in hooking up too, granted they’re a lot slicker about it. But the sexes have never been so close in regards to similar dating behaviors.

We’ve got it backward. People only want to wait for a little to have sex if they really like someone but if they don’t give a shit about you, they’d happily rip your clothes off. Some people operate with the mindset of sex and nakedness first. Get to know your heart and soul later. It’s easier for people to be physically vulnerable than it is emotionally vulnerable. For example, I have a much better chance of giving someone the naked time of their life instead of them ever opening up to me about their hopes, dreams, and relationships true desires!

Sex is not bad for the record, it’s an amazing part of the dating process. But often when both people are not clear about their intentions and are content to keep sleeping with each other till one of them calls it. Nothing good comes of it. It leads to both parties growing more jaded of the entire dating process in general. That, in turn, creates this passive heartache they carry from “situationship” to “situationship”. This is when you’re already doing all the things that a relationship consists of without a title. Sex makes things a little murkier. Back in the day, you needed the title of boyfriend or girlfriend before sex was even a thing. Sure there were hook-ups and one night stands, you meet someone at a bar and you may or may not hook-up. But they were not pre-mediated like they are now, the moment you swipe right. Now that’s no longer needed. The lines are a little harder to see. Unless you’ve both clearly communicated what you’re looking for, tread carefully. Both being on the same page makes first time sex amazing!

3. “Too Cool” to care

Every song, every quote, or every sentence uttered these days when it comes to dating reeks of people trying too hard to “not care”. In dating now showing how you really feel and getting vulnerable with someone is seen as a sign of weakness. Which is kind of hilarious when you think about it. Because when you’re vulnerable it allows two people to truly connect.

Where even more hilarity ensues is the people who are in complete denial. Refusing to show hurt, frustration, or even the smallest sign of emotion. When in reality we all see right through it. It’s like the tough guy of the group who goes to a haunted house and protests till the very end he’s not scared. But screams his lungs out at every turn or jump scare.

Dude, you’re scared.


It’s sad really because there’s little to no real reward or appreciation for most people who are open and emotionally available. They on occasion get the least amount of respect when it comes to the cutthroat world of dating.

People get into the same pattern of “relationship chicken”. Where neither one expresses how they really feel in order to play it cool. So they both end up feeling dejected and decided to themselves, “Well that person couldn’t have been the one, or this process would be easier”. All because they didn’t open up their mouth. Most people don’t learn and doom themselves to repeat the same process with someone else. This time even worse because they never got the closure they wanted before with the last person. All in the silly vain of “Playing It Cool”.

4. People Play Phone Games! (Like it’s an Olympic sport)

Technology is the funniest thing. The more advanced and easier the use of access. The lazier people actually get with using it. When text messaging was introduced it was called the “Instant” SMS (Short Message System)


Yet when people receive a text message you may or may not see they’ve read it and they may text you back 30 minutes later, an hour, a few hours, or even a day. That’s the level of game playing or quite frankly “ Too cool to care” games are being played these days.

Sometimes the game playing isn’t even insidious. But we have access to so much information people overthink things. To something that they’ve deliberated over for so long in regards to when to text and what to respond. A day goes by and they completely chicken out and send nothing.

Your grandma and your mum have probably told you this and I’ll be a part of your unofficial family, too. Be yourself! Wanna text 5 minutes after receiving a text? Then go ahead. Don’t usually text till lunch or after work. Do that. But only if it’s truly how you operate.

But when you feel like you, “have them”. Then you start texting how you always have. They’ll start complaining to their friends that you’re needy or trying too hard then you might get ghosted. Be upfront first! Communicate how you usually do when you’re interested.

5. I want to find the perfect man/woman!

I got knew’s for you kids! They don’t exist.

Humans are incredibly fallible. That’s what makes us so awesome, that’s what makes sports so good to watch, why we love TV dramas and why life is so good. Cause we all make mistakes. But in the age of abundant dating choice. One mistake could take you completely out of the game as you don’t fit someone’s misguided view of relationship perfection.

Every day I scroll through Instagram with these wildly myopic views of dating. Quotes such as:

  • “If they don’t call you, they’re not a real person”
  • “You need someone who’s sexy, spiritual, exciting, rich, in shape, funny, great in bed, and a great future parent”
  • “If a man’s not pleasing you, move on!”
  • “Don’t settle, you deserve the best!”

These bad and misguided “self-love” quotes are everywhere and they all fail to take into account not a single soul is perfect. No one is ever going to fulfill every single box you have and if they do at first they’re bound to crumble on one of them. The first date false pretenses and rose-tinted glasses can only last for so long. The best women or men out there don’t really exist. They’re really good women and really good men sure. But the one “best” man. It is an opinion not based on reality. If someones not pleasing you, you don’t just move on, you communicate your concerns. There seems to be this constant overhanging feeling of unbridled entitlement people have about “what they deserve” and it often revolves around these huge expectations with little to no concern as to what they bring to the table. People think they deserve perfection when they can’t even fathom becoming the person they feel like they “deserve”.

Often someone is written off for such a minor insignificance that in the grand scheme of things means nothing. I’ve had friends break up with women cause they don’t like country or they don’t rock climb with them enough. True story! Then after they’ve written them off they’re looking for someone just like that girl they just dumped. But this time she’s gotta be good at rock climbing. This whole process is laughable.

The media and social media have a role to play too. All these images, perfect human beings, movie stars, and couples who are “goals”. People want all those things. But they fail to take into consideration that it all takes HARD work. If people don’t get that dream perfect person they dip.

It’s not just looks though. It’s that connection too. Sometimes people expect such a quick and expedient connection that if it’s not there after the 2nd date. They cite incompatibility. When in reality. Love is not like that. It goes at a nice steady pace and builds on experiences and shared moments that create love and attraction.

Excitement, travel, wanderlust and super amazing dates on every meeting is the expectation of a lot of people. However, when that all winds down a bit and things start getting regular. That’s when people start questioning if they should leave. They complain to their friends the “sparks” gone when in reality they just have to take the relationship to another level. But they fail to communicate then it’s up in flames. The mental strength and capacity it takes to actually work through things to them is merely folklore. They’d rather cut their losses and “find something new”.

6. “I got too many options!”

Ah yes, what about the options.

Like I said before, people legit feel like relationships are buses a new and better one will always present itself. To some extent this is true. But true compatible relationships are not easy to come by. But if you want someone to hook up with for a few months sure. They’re easy. But that’s the teenage boy’s mindset. We gotta break outta this funk. Don’t give up on people you could be happy with.

The myth of infinite choice is just that. It’s all a myth. You may very well have 100’s of potential matches on a dating app. But how many would swipe back? Let’s say half of them swipe back. How many would respond? Let’s say they respond. How many would agree to a date? Let’s say they agree to a date, how many would actually show up. Finally, if they show up will you actually like each other? People don’t think like this. They always have the mentality that here’s something better. So they move on!

For our parents, their choices might have been fewer, but their sheer excitement and sparks they shared were greater. Because they didn’t have that mindset of, “why work for this when I could find something else”.

I could get a date, the next night right at my doorstep if I said the right things. Hell yeah, I could set height, race, age, sex and location specifications. Shits wild when you think about it. It’s easy for a lot of people to get sucked into that vortex. I have, HBO, Netflix, Amazon Prime, Disney+ and Hulu. I once spent 30 minutes looking for something to watch. I couldn’t choose so I watched an old Blu Ray of Die Hard.

Imagine that in real life.

There’s zero investment or skin in the game when it comes to having “so many options”. The only real commitment you have is swiping your finger and sending some unenthused responses cause your so jaded from the last person.

There are a lot of people in their late 30’s now dating and repeating the same processes and the generation after them will most likely do the same thing. They’re called maximizers.

“What’s that?”

Well, it’s when they use “Maximizing Behavior”. It’s as if they treat relationships like shoes. They try a shit tonne on before and run them to the ground, break the heels and then throw them in the garbage. Cause they’re looking for the perfect fit. They believe with all their muddled philosophies that there’s a perfect person (chuckle) So they’re trying to maximize the shit out of everyone. These people are kinda nuts though, cause even when they’re super happy and want to write a limerick about the person they’re dating or even in a relationship. They’ve still got their ear to the ground cause there might be something better.

Watch out for these people! They’ll break your heart and happily skip to the next person so fast your head will spin.

7. People really like being alone.

If I had a dollar for every meme I saw of someone gleefully staying home and canceling plans to be alone. I’d be rich as hell. I’d be paying someone to type this at 8:00 pm after toiling away on my fat belly at the gym. People brag about this, about missing an opportunity to either build or continually cultivate relationships with people. Human connection is what life’s about! But more people, would rather chill at home all night and watch Netflix. Look I love some binge-watching. But human interactions should always come first IMO.

People are so committed to self-love it barely lends anytime to potentially falling for someone else. It’s very happy and rewarding to set goals and accomplish things by yourself. But for some people, they get consumed and forget to make time for anyone else to potentially share that joy with them. This, in turn, makes it so much harder for people to date cause they’ve built such a heavy forcefield of friends and family, they’re very much hard pushed to even consider marginal plans with anyone else. Most people are very much okay being on our own. But this engages us in a very persuasive comfort zone where you could never quite see yourself leaving. Unless it was the “right person”

Goes back to people literally searching for reasons to disqualify you! Because deep down, people sometimes don’t want to work for what they want. They are happy to go back to being alone and having it their way. Being alone is good for growth to some degree. But too much of it lends itself to selfish tendencies. You might be so used to having things your way cause you’ve been alone for so long. So when I perfectly good person comes along. You’re not willing to lose some natural facets of selfish tendencies. Then it’s back to square one again. Rinse and repeat.

8. Situationships are the new relationship

These days if sex is happening and you’re doing some things that are featured in a relationship, It’s an easy route for some people. The road traveled with the least resistance and perfect scenario for someone who doesn’t have the emotional maturity to make an adequate decision on spending time with someone. It’s also great for rebounds so it makes perfect sense why people are falling into that trap. They work so well cause to a lot of people it feigns a relationship. To the other person, they might think they’re in a relationship. But remember most people don’t open up about what they want so the other person in the “Situationship” gets away with it. That’s why they last for so long. Or on other occasions the person who would rather be in a relationship. They lie to themselves. They tell their friends they’re fine with it and it’s what they want too. Till they break! They finally express how they feel. By then, it’s too late. But this is our current reality of monogamous commitment. That’s if you’ve even had the discussion if they’re seeing anyone else. Cause if you haven’t it will be their excuse to continue seeing other people until you “open up”.

I got news for you, you have yourself to blame and yourself only for letting it get there. You’re worried it’s not going somewhere! Say something?! Close mouths don’t get fed. It really is that simple. If you’re worried about losing them cause you’re expressing what you really want. They’re not for you. Stop wasting time, you’ll never ever get back! People complain and put cryptic posts online about someone not being honest with them and leading them on. Did you ever ask? I mean really ask? WE gotta stop Playing the victim roles and take action!

Also, be honest and real from the get-go. I.E when I hear this, “I’m not really sure what I’m looking for right now, but If I see something going somewhere I’d potentially consider getting into a relationship”. Just say, “I’m looking for a relationship”. See how easy that is? If you’re just looking to hook up, tell them the truth. You only get from life what you manifest. If it’s been 4 or more months and the other person is, “Just unsure right now”, or “ I want to get to know you some more”, “not sure what they want”, “still hurting from the last relationship”. Leave!!!! They’re never going to commit. I promise you.

Also, go for the “jugular of truth”. Be straight and direct from the get-go. You will have slightly fewer options cause you’ll weed out the time-wasters but go for the raw honesty. If not you’re doomed to cloudy uncertainty and time wasted. If you knew what someone was truly thinking dating would be a breeze. But you don’t. The closest way you can get to that is by asking.

9. People are ruthless. They have no remorse.

Accountability for breaking someone’s heart is nonexistent. People will happily ghost and that same week hook up with someone else. Even the person you thought was a “good guy/woman”. Trust me they got it in them. People don’t feel the need to apologize profusely for upsetting someone’s feelings or ending the relationship abruptly. The attitude now is, “You gotta respect my feelings and opinions so I can self-love and do me”. Me, me and me. There is no, “sorry if I’ve led you on I really wanted to make this work and I’ve had a good time”. It’s just cut the cord and move on. We honestly feel like a person’s emotions are a moot point compared to us. It’s for them to figure out. People don’t allow someone time to talk it out and get the closure they need. They rather cut the cord or not cut the cord at all!

A large majority of people feel like, you hurting is your problem. It’s got nothing to do with what they said, you have the issues, not them. What you have to realize is that people need to talk things out and express their side of things. Even if you’re done. Closure matters.

10. Why are we all so JADED!?

Yo! We’re jaded as fuck.

I hate that word cause it’s such an overhanging cliche that’s so overused by any modern media when they talk about Millenials and dating but it’s true!!! We’re so jaded our heads hurt. A large majority of people are stuck in a tornado of jaded apprehensions before they step foot in any dating location.

Here’s the modern dating formula :

This is the new wave.

If this process is repeated 5 times or more you’re bound to be damaged. The scary thing is most people are not trying to fix this. They’re very happy to repeat those same mistakes. Hoping they’ll find someone.


In order to change, I mean truly change you have to be willing to do things differently.

We value sex so damn much and find ourselves slowly falling into “hook up” culture. It messes with your head. Some people fall into it unknowingly. They’re so used to the same scenarios they don’t even realize that they might be part of the problem.

People being hurt and unheard so many times leads them to become the very things they once hated. They feel like this, “Why even be me and open up, they’re only going to fuck me over anyway.”

That mentality leads to them communicating poorly, not making an effort, texting whenever they want, flaking, ghosting, not really being honest about how they feel, and generally being a large part of what they were once privy to. So then we have a horrible vacuum and an accumulation of everyone mirroring poor dating behavior because someone else gave us this experience.

An eye for an eye makes the world go blind. We’re slowly creating a dating wasteland. I legitimately feel sorry for people who are coming out of a 6+ year relationship. Or coming out from divorce. They’ll get eaten alive. Unless you’ve got experience with the current dating scape. I’m with you I’m an ally and I’m here to guide you through this process.

People’s romantic minds are muddled with things from their past they’ve never given themselves time to heal because they haven’t had to. They just break up and join a dating site. That’s it. So it allows people to meet with so much hurt they start to wonder if it’s all died out. If love was something created by Hallmark or if it truly exists.

We all have wounds that need healing. Take note of that term. “Need healing”. You need to work on yourself before you enter the realm of modern dating as we know it. Every date I’ve been on the woman has lightly touched on being hurt by the last guy. Because of me knowing this it’s a chance for me to remind myself not to be that guy. To be the person that’s honest and open so there’s no room for me being a terrible story of hurt and pain in their life. Don’t use your past trauma as an excuse to remain aloof to someone who might actually care for you and want to be there for you!


Is dating in 2021 hard?


But there’s never been a better time to date. More than ever despite the traumatized people that are still the majority of the dating population. There are still a decent amount of people looking for real connections more than they ever have been before, outside of cell phones, with a real person who wants the same things and craves the same passions. These are the people you want. The people who’d rather call than text, the person who’s upfront from the beginning and that person who is so naturally in tune with you and see’s you as 10/10 human being. Be what you want in someone and you’ll naturally attract them.



Trey Hamilton

Author - The First Date Fix - Dating Coach - Content Creator -Dog Dad | follow me for some ramblings of a millennial who has dated. A LOT! TheFirstDateFix.Com