Types You Date in Your Twenties
Published in Humans
If I had to choose three words to describe my twenties: sex, drugs & Don Julio.
I’m not sure how to be more direct than that, but if you want something slightly more thought-provoking, let’s go with—invincible, untamed, and outspoken.
My twenties were a time—a great time to be alive.
Manhattan was busy as hell. You still tipped bartenders in cash after every round—none of this running a credit tab crap and tipping the bare minimum at the end. You could grab a bite at three in the morning at L’Express, and sniff a line off their table without anyone kicking you out. Your nights out were pure living in the moment, because no one was focused on taking photos and then spending the next morning writing cheesy Drake captions. The ‘next morning’ consisted of catching a cab before people going to work spotted you in stilettos and a mini skirt at seven in the morning in Queens.
And yes, we rode home with a bag of something in our bras. High and proud of it too.
I was young. Reckless and wild. If you didn’t go to Pacha for Chus & Ceballos, or Veranda on a Thursday, or 1Oak on a Sunday, or eat sushi or Thai food before a bartending shift, or go on two dates in one night, were you even really living?
Despite the wild moments, I was still self-aware. You didn’t walk around glued to your phone ten years ago. You didn’t film your food. You didn’t make ‘get ready with me Reels’ or post every single outfit you wore on the daily. There was mystery. There were lies. There was truth. Maybe that’s why there was an art to dating.
Maybe, that’s why back then we were able to go out with different types of people. We didn’t know everything about someone before sitting across from them. Today, one scroll through someone’s Instagram can tell you whether you want to pursue them before they’ve even opened their mouth.
Eight to ten years ago, people were alive. They were learning—they were going through the motions without Googling why they were feeling the way they were feeling, or why he’s not texting back fast enough. People were more in tune with themselves without constantly outsourcing their advice and reasoning. This made the connections we built feel more real.
The types I’m about to present to you aren’t all daisies and sunshine. Some were fun. Some were terrible decisions. Some wasted years of my life. But they still had substance. And they all taught me something.
(In no particular order):
Type 1 — THE OLDER GUY
This type came around a few times . It wasn’t necessarily that I was going after older guys. They were going after me—and I reciprocated.
At twenty-something years old, when a guy in his 30s offers to take you to a restaurant your average 23-year-old can’t afford, you’re going. Unfortunately, the aftermath of dealing with these types usually comes with a whole bunch of unwanted shit: jealousy, possessiveness, stalkers, cheaters, players—you name it.
They waste a lot of your time. And sometimes, they take up the years you could’ve spent meeting someone closer to your age—someone you could actually grow with instead of inheriting whatever baggage he dragged out of his last relationship. The emotional roller coaster isn’t worth it.
When you’re younger, an older guy has an easy weapon to use against you: your age. You question something? You’re overreacting. You catch him being dishonest? You’re immature. You want better communication? You’re clingy. You ask too many questions? You’re nosy.
Somehow, his shitty behavior becomes evidence of your immaturity. If I could redo my twenties, I would’ve avoided this type at all costs. When you’re 20, you’re in your prime. Dating someone significantly older sometimes just means dating someone else’s old baggage that’s still sitting on the curb.
Yep. I said it.
Type 2 — THE DEGENERATE
This type comes in all shapes and sizes, which is why you don’t always catch it right away. They weasel their way into your weekends, gradually seep into your weekdays, and before you know it, you’re sleeping in on a Monday and skipping your 8 a.m. Psych class.
This type doesn’t have a “real job”—or at least not the traditional 9-to-5, checking-in-with-a-boss kind of job. They turned their side hustle into their main hustle. They work their own hours and, conveniently, start treating your schedule like it doesn’t exist either.
Slowly but surely, your routine starts disappearing. Sunday family plans? Missed. The gym? Tomorrow. Your friends calling? Ignored because you’re battling a hangover and wondering why your serotonin feels like it left the country. That’s the danger with this type.
The constant excitement blinds you to how disruptive their presence actually is. You’re always going somewhere, doing something, meeting someone, ending up at some “fun spot.” Until eventually you realize you’ve been living entirely inside their world, sucking you dry. And somewhere along the way, you stopped taking care of yourself.
Type 3— THE WISE ONE
This is my favorite type. They usually only come around once in a lifetime—and somehow stay for most of it. This type normally starts as a friend. You don’t technically date. Maybe an unexpected kiss happens somewhere along the way, but he knows his lane.
He’s grounded, level-headed, a great listener, and even better at giving advice. He seems to know you like a book, and you’re comfortable enough around him to tell him almost everything happening in your personal life.
I’ve had this type in my life since I was 17. He pops in and out. We catch up. There’s harmless flirting. It’s one of those situations where you both know he likes you—and probably always wanted something more—but somehow it became a right-guy, wrong-time, but-also-not-quite-for-me situation.
He was intelligent. We had deep conversations. He questioned my perspective on life. We could sit in the most low-key places and talk for hours. I probably could have dated him. But I didn’t want to lose him as a friend.
I sound annoying. I know. But deep down, I also knew it wouldn’t work romantically. He wasn’t the risk-taker. He wasn’t the adventure I was searching for at that age. He played it safe. And back then, safe just wasn’t for me.
To this day, we remain close. Sometimes he’s bitter. Sometimes he’s better. But after all these years, he’s still the type of person I’d trust to pull me out of whatever I managed to sink myself into.
Type 4— THE ONE THAT ‘LOVES’ YOU
This type gets messy. At first, you’re friends. Then it slowly develops into something more. You become attracted to how much they seem to need you. You want to help them. You feel wanted. Meanwhile, they become more attracted to your physical appearance than your actual mind. Then they “fall in love” with you.
And this, my readers, becomes that toxic relationship we all go through. We get sucked into the pits of darkness by these types, swallowed into the belly of the beast, and somehow a year—or two—passes before we finally wake up and say: F this.
This type is usually oozing insecurity. Jealousy. Money problems. Probably doesn’t exercise unless you push his ass into the gym. And, of course, he has a group of guy friends he vents to about you. His friends don’t like you because all they hear is that their “boy is unhappy,” so naturally, you become the problem.
But the bigger problem is that this type doesn’t actually want to understand you. He wants to reshape you into their ideal partner rather than seeking a better-suited one. Your behavior bothers him. Your personality is too much. Your choices embarrass him. Morally, you don’t quite meet his “standards.” Yet somehow he still wants to date you.
These types don't take the time to understand how your mind works. They like how you look, they're attracted to you, and for a while, that's enough. Unfortunately, sometimes it’s enough for us, too. We get off on how attracted they are to us. The physical connection convinces us there must be something deeper underneath it. By the time we realize there isn’t, we’re already in too deep.
Type 5 — MR. RIGHT NOW
This type fits conveniently into your life. He has his own schedule, but makes himself available for you. You have enough in common right now to convince yourself there might be something there. Maybe you live near each other. You like the same restaurants. You both eventually want a relationship. You enjoy spending time together. Everything seems to flow smoothly. For now.
But having the same interests, compatible schedules, and someone to “hang out” with isn’t always enough to make you crazy about somebody. The company is good. The conversation is easy. Nothing is technically wrong. And yet...Where’s the depth?
That’s what Mr. Right Now teaches you. Nothing has to be dramatically wrong for someone to still not be right for you. Some relationships exist to show us what we want more of—and what we can live without. Some people give us exactly what we need during one particular phase of our lives.
That doesn’t mean they make the final cut.
Type 6— THE DEBATER
This type is your polar opposite. He pushes you to your limits, gets completely under your skin, and somehow you can ignore each other for three days and come back like nothing happened.
He’s passionate about every cause. He knows everything happening in politics. And God forbid someone mentions gender roles in relationships because now you’re trapped in a three-hour conversation you never asked to be part of. This type came into my life in my mid-twenties. His passion was attractive. Our worldview was not.
We debated every single thing in the book—vaccines, prenups, who should be the breadwinner, abortion, immigration in America. The list goes on. Looking back, I genuinely don’t think we agreed on one thing. You’d think after enough drinks, when we finally made it back to his apartment, all that arguing would translate into some insane sexual tension.
Wrong.
Let’s just say things were dry. And not functioning.
Type 7 — THE LATE-NIGHT CALL
Ahh, the late-night assassin. The 4 a.m. hookup. The one who works a real job and doesn’t party like you do—but somehow will still let you into his condo at four in the morning for a f*** session. We’ve all been someone’s booty call or had one at some point. And if you haven’t, I’m impressed.
Because nothing is quite as humbling as realizing someone is perfectly happy sleeping with you but has absolutely no intention of taking you seriously.
This type comes into our twenties to teach us three things: Shame, guilt, and respect.
Shame is showing up at someone’s place drunk as a skunk for a quickie while knowing the one rule before you even get there: You can’t stay over.
Guilt comes when you realize this person actually checks a lot of the boxes you’d want in a relationship—but he treats you like a sidepiece because somewhere along the way, you helped establish that dynamic.
And how do they teach us respect? You learn that afterward. Because sometimes you have to experience what it feels like to completely disrespect your own time before you finally understand how valuable it is.
Can’t have the love without feeling the pain first, right?
Type 8 — THE ‘ONE’
n my opinion, somewhere around 27 is when the idea of actually settling down starts to make sense. Anything under 25? Mostly a learning experience. Think about who you were at 23.
Then 25. Then 27.
The difference in your thought process, the people you date, the things you tolerate, and what you actually want out of life can be completely different. We grow up a hundred times over in our twenties. The type of man I dated at 23 is absolutely not the type of man I would want to be married to in my 30s.
The type I met at 27, though? That turned out to be someone I’m still with in my 30s. When I say “the one,” I don’t necessarily mean some cosmic soulmate who was destined to appear. I mean the type with actual potential to become a life partner.
By 27, I was more grounded. More stable. More domesticated. I wasn’t running around with the same wild circle of friends I had five years earlier. Suddenly, traveling sounded better. Waking up early wasn’t a punishment. I wanted chill restaurants, books, mornings, actual plans. The dingy lounges, being in “the scene,” and staying out until all hours stopped feeling exciting.
And when my mindset shifted, so did the type of men I was attracting—and, probably more importantly, the type of men I was attracted to.
That’s all I’m saying about this type. Maybe there’s a Part 2.
Which one did you date? And don’t tell me none of them. We all had at least one Older Guy, Degenerate, Mr. Right Now, or 4 a.m. mistake somewhere in our twenties. Maybe yours taught you what you wanted. Maybe he taught you exactly what you’d never tolerate again. Either way, some people were never meant to stay—they were just there long enough to teach you something.
Tell me which type I missed. Because I already know there are a few. And if this felt a little too familiar, send it to the friend who survived your twenties with you.
