Dating in Your 20s: A Millennial’s Dating Advice
Dating in your 20s is like a house with two wives; you know something is going down for sure!
In the words of the great Mathew McConaughey; “Alright, alright, alright”, time for you to fess up something:
Who here remember the Wild West days of Tinder, where bios promised “world traveler” but delivered “guy whose peak was high school track”?
Yeah, we’ve all been there only to be left with a reality check that could rival a bad case of food poisoning.
Dating in your twenties, my friend, is a glorious mess.
Think music festival; fast-paced, overflowing with options, and a high chance of getting sprayed with something questionable (both literally and metaphorically).
You were a master juggler, keeping multiple dates spinning like flaming batons because sleep was for the weak when a potential spark was just a swipe away.
But a decade later, things take a sharp turn.
Those blurry 2 am texts morph into the deafening silence of a notification-less inbox.
Dating in your thirties? Think jazz bar; slower, more discerning, and not everyone get it.
So I decided to take the jump and explain what dating might look like if you were in your 20s vs 30s as your trusty 31-year-old Millennial guide.
This two-part series is your ultimate guide to surviving (and thriving!) in the world of Millennial dating (You’re in too Gen Z).
This part one tackles the chaotic, exhilarating rollercoaster ride of your twenties.
We’ll dig into the questionable choices you probably make or have made (because, let’s be honest, who hasn’t?).
Then, we’ll go through those hilariously awkward first dates that make the best stories, and how these experiences shape you as a dater in your thirties.
Part two, goes into the often-stereotyped yet equally complex world of dating in your early thirties.
I’ll be spilling the tea on the realities of “Netflix and chill” versus finding something real.
We’ll explore the challenges (and potential rewards!) and share some valuable lessons learned (the hard way, of course) to help you up your dating game.
So, are you currently battling the trenches of dating apps in your twenties, or curious about what awaits you in your thirties?
This series is packed with relatable stories, dark puns and moments, and some insights backed by science to help you suck-less in your dating life.
Let’s get real and let’s not waste anytime.
Dating in Your 20s: Priorities and Mindset
Ah, your twenties.
A glorious, confusing time when your dating life can be summed up in two words; flavorfully chaotic.
Why is it a glorious mess you might ask?
Well, a study by NIH found that not all young adults in their 20s are in committed relationships.
The study found that only 33% of young adults aged 20-25 reported being in a committed relationship while 40% were not in any romantic relationship.
In a nutshell, you are less likely to pursue long-term relationships in your 20s.
Now, everything you’re about to read isn’t necessarily something that will happen to you.
After all, there are many 20-something guys and girls who are having the best relationships compared to those even in their 40s.
So think of this as what most would do during that time because not everyone has figured things out by then.
Ok, now that is out of the way, let’s carry on.
Let’s face it, we’ve all been there (or at least swiped right there).
The allure of a new fling is intoxicating, and sometimes a night of bad decisions feels way more appealing than, you know, adulting.
So, what’s inside that flavorful mix?
Let’s unpack this wild ride.
Hyper Exploration
Often takes the center stage of your time and who can’t blame you after all!?
Your body is a temple, sure, but sometimes it feels like a temple open for tours 24/7.
If I were to speculate, I’d say your dating life is like a buffet – there are a lot of options, and sometimes you just want to try a little bit of everything.
The problem? Buffet overload can leave you feeling gross and unsatisfied.
A string of meaningless relationships might feel exciting at first, but it can leave you feeling empty after the tequila wears off.
This could undermine your dating life later on.
Imagine waking up next to someone whose name you can’t remember, only to discover they have a disturbing collection of My Little Pony figurines.
Now, suddenly that Netflix marathon with your cat starts looking pretty appealing!
External Validation
It becomes your not-so-secret superpower.
People with a need for external validation might be a sign of low self-awareness.
A like on your dating profile feels like a victory lap, and a text message is the ultimate validation of your worth.
Remember that time when you decided to have the perfect date?
You spent an hour crafting the perfect witty bio, only to get a generic “hey” in response?
Yeah, that stinging feeling of rejection is real.
The problem?
This constant need for external validation can leave you feeling lost and unsure of who you are outside of the dating game.
It’s like constantly refreshing your Instagram feed, hoping for more likes – but neglecting actually to post anything interesting yourself.
The Lack of Clear Passions
This is like the Godfather of most of us in our 20s that adds more mud to the dating waters.
You’re still figuring out who you are, what you want, and where that inflatable dinosaur pool float fits into your life goals.
This can make it difficult to connect with someone on a deeper level beyond superficial talks.
Imagine trying to have a deep conversation with someone whose hobbies include “breathing” and “watching paint dry.”
Not exactly the recipe for a long-lasting romance.
Group Dates and Friends’ Approval
When it comes to dating in your 20s, going solo is so 2010.
Instead, it’s all about the group date. Let me explain.
Most singles are swiping right on whole friend squads to gain stamp(s) of approval from their trusted confidantes.
It’s like getting your potential date pre-vetted by a committee.
Your friends become like The Bachelorette producers, grilling your prospects:
“So Chad, how do you feel about putting the toilet seat down?”
One wrong answer and it’s a limo exit!
What matters is mostly this to you probably:
Do they get along with your girl/guy or trigger more side-eye?
They’re automatically benched from your roster if they can’t hang with your crew.
How many times have we texted our friends then to brag/screen our date?!
But the ultimate group stamp?
Getting those fire emojis under your new couple pic from all your BFFs.
In the social media age, the like is the new stamp of “I like you.”
Physical Attraction
Let’s be real, in your 20s, dating is a bit like going grocery shopping when you’re starving.
You’re immediately drawn to that delicious-looking candy at eye level without checking the nutrition facts too closely.
When you’re young and restless, the initial “candy wrapped in a human” spark is hard to ignore because of the variety.
But just like those sugary cereals from your childhood, initial attraction can turn boring once the novelty wears off.
That’s not to say physical chemistry isn’t important (it is important!).
Just don’t be surprised if that luxurious hair and the electric smile aren’t all that matters later.
And most of the time, they will show that in a way that makes you question your decision to be with them, to begin with.
But you choose to ignore it or ride it off.
Why? Well, we are still young right?!
Conflict Resolution in Your 20s. What?
It’s less about finding common ground with your partner and more like a poor episode of The Hunger Games.
Is this you as well?
Here’s how we “resolve” conflict when we’re still figuring out adulting in our 20s in my observation:
The Silent Treatment
The Public Disagreement Display
raising your voices, dramatic hand gestures, and enough collateral emotional damage to leave your friends questioning their brunch plans.
Your Friends Intervention
Pro tip: When your friends start suggesting couples therapy as a joke, it might not be a joke anymore.
The “Competitive” Breakup
Things are not going in your favor.
So now it is time to break things off, but here’s the caveat.
This one involves keeping score on who can move on the fastest.
Think rebound relationships that fizzle out quicker than a birthday candle, and a desperate need to prove you’re “doing just fine” on social media.
Admit it, you did that!
Imagine strategically posting photos of yourself with every single attractive person you meet, just to show your ex what they’re missing.
(Spoiler alert: Most of the time, they’re probably just cringing and mostly cultivating a revenge plan).
The 3 am Apology Text
A Date on a 20-Something Budget
As if everything wasn’t enough already!
The struggle is real when it comes to your finances on a young adult’s budget.
Dates turn into elaborate strategizing sessions.
Deciding where to go can feel like a high-stakes poker game.
Do you play it safe with the classic movie-and-pizza combo, or gamble on that trendy new place that requires a small loan (and a side of anxiety)?
Mom’s Matchmaking Mishap
Am I the only one to say that my mom tried to connect me with a girl she really liked back in the day?
Enter “the ever-present danger of the “Mom Knows Best” blind date”.
Bless their hearts, our parents just want us to settle down.
But sometimes their choices of a “perfect date” are just too much to handle.
Imagine your well-meaning mother set you up on a date with someone who collects porcelain dolls or whose karaoke skills are best described as “enthusiastically tone-deaf.”
Suddenly, that childhood vow to never marry someone your mom picks seems prophetic.
Let me give you a real example and you’ll understand why I chose the ‘dolls’ here.
Take Emily.
Her mother, ever the optimist, decided to set her up with “a lovely young man who shares your passion for porcelain dolls.
” Emily, who hasn’t touched her childhood porcelain collection since the invention of the internet, stared at her mother in disbelief.
Fast forward, the date arrived, and it turned out “lovely young man” was a euphemism.
He wore a sweater vest that could double as a museum exhibit and spoke in a voice that resembled Professor Snape after a particularly bad day.
His passion for porcelain dolls, however, was genuine.
He spent the entire date showing Emily his prized collection, complete with historical anecdotes and meticulous cleaning techniques. (I don’t know about you but this is like a horror movie scene).Emily, torn between amusement and awkwardness, excused herself to the restroom.
There, she texted her friends a play-by-play of the date, complete with emojis and dramatic pronouncements.
To her surprise, her date emerged from the stall next to her, phone in hand.
Turns out, he was also texting his friends about the “charming yet slightly terrified” woman his mother had set him up with.
Let’s just say that at this point, they both decided that this wasn’t going anywhere.
Moral of the story: Pick your own date next time.
Oh, this also reminds me of your friends, in particular ‘the wingman’ who also does something similar to your mom sometimes.
Here’s a golden rule:
A good wingman respects your choices, even if they don’t always agree with you.
If they’re not doing so, they shouldn’t be your wingmen.
A good wingman should offer you support, boost your confidence, and occasionally be there for you for that post-date debrief.
After all, sometimes the most unexpected connections happen with a little help from your friends.
The Fixer-Upper Fantasy
Also known as “remodeling a walking red-flag factory partner”.
It’s like scrolling through a property app and falling madly in love with that charming Victorian mansion.
And you do so while completely ignoring the leaky roof and the faint whispers of left-out spirits.
In the world of dating, this translates to falling for someone with the emotional stability of a fidget spinner and the maturity level of a sassy toddler.
You see potential, a diamond in the rough, someone who just needs your “unconditional love” to blossom into a responsible, emotionally available adult.
Here’s how the “fixer-upper” fantasy usually plays out:
You meet this hot charming girl, even if her charm comes with a side of crippling indecisiveness and a complete inability to hold down a job.
Then you convince yourself that her constant need for emotional reassurance is just a “quirky communication style”.
You also think that her questionable life choices are simply a “cry for help”.
And to top it off, you ignore all of that and you keep it on with her.
Months (or years, because denial is a powerful pill) later, you’re drowning in a sea of emotional debris.
Her “potential” remains unfulfilled, and your patience has worn thin.
You finally realize that you can’t love someone into becoming a person they’re not.
Now, you are starting to have second thoughts about every bit of emotion you had for her.
The moral of the story?
Look for someone who’s already built to last with passion to grow and become better, not someone you have to assemble yourself from spare parts.
Dating should be fun and enriching for you and them at the same time, not a never-ending DIY project.
Yes, you can help them become better or make their life easier in some ways.
But, if they can’t seem to be willing to actually make their life better, leave.
Such partners tend to be emotionally unstable and often are terrible to be with in the long run.
Stick to one who has a sense of responsibility, healthy outlook, and (bonus points!) knows how to use a dishwasher.
Now that’s one worth swiping right for.
Opportunities For Good Dating in Your 20s
Dating in your twenties comes with a lot of experiences – some amazing, some…well, let’s just say memorable.
You’ve dodged some questionable bios and people. Survived first-date disasters worthy of their own sitcom.
And maybe even learned a thing or two about yourself, which is the most important part.
Now, here are some ways and science-backed insights to leverage those experiences for more fulfilling relationships as you move forward.
Think of it as graduating from the School of Hard Knocks (Dating Edition) with honors.
Define Your “Why”:
Before diving headfirst into the world of swiping, take some time to reflect on what you’re truly looking for in a partner.
Are you seeking casual connections, something more serious, or simply enjoying the experience of meeting new people?
This will help you attract compatible matches and avoid wasting time on dates that don’t align with your goals.
Communication is Key:
Open and honest communication is essential in any healthy relationship, even in its early stages.
Practice expressing your needs and wants clearly, while also actively listening to your date.
Don’t ghost someone you’re not interested in – a simple, honest message goes a long way.
Some people ghost because it’s easier and don’t involve any potential conflict.
This is why so many self-sabotage as they grow older with many limiting beliefs.
So train yourself to face things head on and don’t be passive.
Trust me, it’s a great weapon to use as you get older.
Know Your Worth:
Confidence is attractive!
Focus on building healthy self-esteem and believe in what you bring to the table.
Don’t settle for situations that compromise your values or self-worth because that will leave cracks in your own growth.
Here, use the process of elimination.
In other words, it’s acceptable to see multiple people simultaneously to figure out what works best for you.
Embrace the Learning Curve:
Dating is an experience, and every interaction (good or bad) can be a learning opportunity.
Reflect on what worked well in your dates and what didn’t and what you’d like to do differently next time.
The key here is to be open and ego-free.
If you always blame your dates for any mishaps, you’re potentially not being honest.
They could be the worst for sure, but set your ego aside and think about it deeply.
If you are always getting rejected or end up in unfulfilling dates, then that’s on you!
Work on your ‘why’ and be willing to communicate your needs first.
Find Balance:
Dating is important, but it shouldn’t consume your life.
Make time for your passions, friends, and personal growth or studies.
A healthy balance will not only make you a more well-rounded person, but it will also make you more attractive to potential partners.
If you ask any ‘healthy’ girl or a guy if they like someone with no passions or hubbies or a plan in life, they will say ‘no’.
Boundaries Are Your Friends:
Set clear boundaries for yourself and communicate them with your dates.
This may involve things like physical touch, communication expectations, or how much information you’re comfortable sharing at first.
Nothing beats a person who holds their ground firmly on what they believe in. Remember that!
My Personal Bonus Tips:
Believe people when they say they’re not ready for a relationship.
Don’t force anything. The doesn’t make you the hero or Shakespeare if you persist doing so.
Give your partner the benefits of the doubt a few times. Then have a discussion if they keep ‘causing’ you to feel a certain way.
If he or she doesn’t text you after a while, that doesn’t mean they’re out there cheating on you. Hear them out first, then discern.
Don’t date your friend’s ex behind their back. Be frank about that with them first. A good friendship is priceless.
Rejection is normal and happen to all of us. It is a natural part of dating and does not define your self-worth.
Dating apps are ok. But they shouldn’t take away your chances in approaching in real life. It’s way more enriching!
Go to your dates with the mentality “I wonder if this person fits my criteria and ideals”. This will take the pressure off of yourself.
At the end, your 20s are the prime of your life.
Try new things, join clubs or activities that align with your interests, and expand your social circle.
The more people you meet, the more chances you have of finding a connection that clicks.
Remember, dating in your 20s shouldn’t feel like a chore.
Have fun, work on your future, expand your self-awareness and understand your attachment.
Trust me, these 3 points are the difference between a happy and toxic relationships later on and your own maturity as well.
Take it one step at a time and allow yourself and your partner to learn more about each other and see the future compatibility between you two.
Hope you enjoyed this post.
I’m curious, what is one bad date you had that you still remember/ What have you learned?
Hope to hear from you 🙂
