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20 Things You Thought Were Cool in Your 20s (But Aren’t Anymore)

Updated on August 1, 2025 by TMM Staff · Lifestyle

A group of friends raising beer bottles in a celebratory toast at sunset.
©Getty Images/Unsplash.com

Your 20s feel like a free trial for adulthood. You get to experiment with identity, push boundaries, and wear sunglasses at night, thinking you’re making a statement. Some of it actually works, but let’s be honest.. most of them didn’t age well.

Table of Contents

Toggle
  • 1. Partying on weeknights
  • 2. Owning more shot glasses than plates
  • 3. Sleeping on a mattress on the floor
  • 4. Constantly switching jobs
  • 5. Eating instant noodles for dinner every night
  • 6. Posting every thought online
  • 7. Clubbing till sunrise
  • 8. Bragging about how little sleep you got
  • 9. Living off energy drinks
  • 10. Wearing ironic graphic tees
  • 11. Avoiding the doctor at all costs
  • 12. Thinking chaos equals fun
  • 13. Getting tattoos without much thought
  • 14. Living paycheck to paycheck and laughing it off
  • 15. Constantly moving apartments
  • 16. Saying yes to everything
  • 17. Dating for chaos, not compatibility
  • 18. Caring too much about being “cool”
  • 19. Letting clutter pile up
  • 20. Thinking that turning 30 meant getting old

By the time your 30s roll around, a few things you once swore by now just look… kind of tragic. Here’s a reality check for the 20 things that felt like a good idea back then, but kinda make you cringe now.

1. Partying on weeknights

A group of friends singing and dancing together at a lively karaoke night.
©Getty Images/Unsplash.com

That midweek bar crawl used to feel like a lifestyle choice. Show up to work with a hangover and a coffee the size of your head? Badge of honor.

These days, staying up past midnight on a Tuesday feels like reckless endangerment.

2. Owning more shot glasses than plates

A wooden tray with three shot glasses filled with dark liquor on a checkered tablecloth.
©William Krause/Unsplash.com

Collecting shot glasses from every trip or event felt like building a shrine to your youth. Bonus points if they were neon.

Now, the only glasses you care about are the ones that can hold a full pour of wine or a strong, cold brew.

3. Sleeping on a mattress on the floor

A cup of coffee placed on a speckled concrete floor next to a bed with white striped bedding.
©Valeriia Miller/Unsplash.com

It was minimalist, or at least that’s what you told yourself while ignoring the fact that it made you feel like a grown toddler.

A real bed frame, maybe even a headboard? That’s the sweet spot. Your back has opinions now, and they’re not shy about voicing them.

4. Constantly switching jobs

A mechanic lying on a creeper under a car, working in an auto repair shop.
©Pablo Merchán Montes/Unsplash.com

Jumping from one gig to another gave you street cred. You were “finding yourself” or “refusing to settle.”

Eventually, you found that job hopping was overrated, and nowadays, you’re looking for a stable job that can get you through without fear of getting sacked. Employers notice consistency, and you kind of like knowing where your next paycheck’s coming from.

5. Eating instant noodles for dinner every night

A hot cup of instant ramen noodles with seasoning oil on top, served in a styrofoam container.
©sq lim/Unsplash.com

A five-pack for two bucks? That was a whole meal plan. Add hot sauce, and you’re practically a chef.

Fast forward, and now you’re scanning nutrition labels and roasting vegetables like it’s a sacred ritual. Turns out sodium overload is literally bad for you, no matter how old you are.

6. Posting every thought online

A person in a white shirt using a smartphone with one hand while tapping the screen.
©NordWood Themes/Unsplash.com

Micro-blogging your life felt like a form of self-expression. Every meal, gym visit, and vague emotional crisis went straight to the timeline.

These days, you’d rather keep some things private. Mystery feels more appealing than oversharing to people who may or may not even care.

7. Clubbing till sunrise

A crowded nightclub with lights, smoke, and people dancing.
©Tyler Clemmensen/Unsplash.com

You danced until your legs gave out, chased by loud music, strobe lights, and overpriced drinks. Sleep was for the weak.

Fast forward to today, and if the event doesn’t wrap by 11, you’re out. If your bros are teasing you for dipping too quickly, you’re doing the right thing.

8. Bragging about how little sleep you got

A couple lying in bed under striped blankets.
©Andrej Lišakov/Unsplash.com

Running on fumes used to feel like a flex. “I only slept three hours” sounded like dedication or hustle culture in action.

Now it just sounds like a red flag. The last thing you want is to show up to work looking like a zombie and staring at the Excel sheet for what feels like an eternity.

9. Living off energy drinks

A group of assorted energy drink cans, including Red Bull, Monster, and Budweiser Beats.
©Garv Chaplot/Unsplash.com

You once believed that drinking sugar and caffeine was an acceptable breakfast substitute. Monster here, Red Bull there.. energy drinks felt like holy water, and boy did you chug it all day, every day.

Now your heart starts palpitating just thinking about it. You have fewer migraines because you actually drink water and keep yourself hydrated.

10. Wearing ironic graphic tees

A person wearing an LA graphic shirt standing beside a colorful graffiti wall.
©Corey Watson/Unsplash.com

If your shirt had a joke, cartoon, or sarcastic slogan, you were making a statement. Usually a weird one.

These days, a clean, well-fitting T-shirt feels more appropriate than anything ostentatious-looking. You’re still making a statement, but it’s one people actually take seriously.

11. Avoiding the doctor at all costs

A stethoscope and medical tools on a white surface.
©Markus Spiske/Unsplash.com

Back then, nothing short of a broken limb could get you into a clinic. You were immortal, or at least you thought so.

Now you book annual checkups like your life depends on it (because, well, it kind of does). You take your health more seriously now, and that’s a good sign.

12. Thinking chaos equals fun

A couple standing by a van, looking at a map on a country road.
©Getty Images/Unsplash.com

Spontaneous road trip with no plans, money, or idea where you’re going? Heck yeah.

But now, you start to get a bit more organized. Instead of hopping onto the next great adventure, you snooze the notifications and get a quiet afternoon nap.

13. Getting tattoos without much thought

A tattoo machine resting on floral design sketches and a metal tray.
©Diana Light/Unsplash.com

Matching tattoos with a roommate you barely talk to now felt like bonding at the time.

These days, if ink is going on your body, it better have meaning (or at least look amazing) forever. You’re done with the impulse decisions, especially if it looks ridiculous on you.

14. Living paycheck to paycheck and laughing it off

A U.S. one-dollar bill with assorted coins placed on top.
©Kenny Eliason/Unsplash.com

You were broke, but it was funny. Financial chaos felt like a shared experience with your friends.

Then one day, that credit card bill made you shed a tear instead of laugh. Budgeting and building savings suddenly feel more thrilling than living paycheck to paycheck.

15. Constantly moving apartments

A cardboard box filled with neatly folded clothes, surrounded by other moving boxes.
©Faruk Tokluoğlu/Unsplash.com

Every lease felt like a temporary getaway. Packing up and starting fresh had its own kind of charm.

Eventually, staying put becomes the real adventure. You start appreciating the luxury of knowing where your light switches are and not figuring out the route to get home on time.

16. Saying yes to everything

A cap and shirt resting on a car dashboard during a rainy drive.
©Andrew Neel/Unsplash.com

FOMO ran the show. You RSVP’d to anything with a start time and a group chat, even if you didn’t want to go.

Now, saying no feels like freedom. Protecting your time is more important than committing to something your mind isn’t 100% fully into.

17. Dating for chaos, not compatibility

A couple holding hands over coffee at a wooden table with a candle and plant.
©taylor hernandez/Unsplash.com

You chased drama like it owed you money. To you, boring was a dealbreaker. The last girl you broke up with because she was too normal? You regret it more each day.

Looking back, it was never about who brought exciting stuff to your life. All you want now is to date someone with whom you can share the last slice of pizza with.

18. Caring too much about being “cool”

A man wearing sunglasses and a floral shirt standing outdoors at sunset.
©Marwan Ahmed/Unsplash.com

You spent way too much time curating an image. The goal was to get approval from people you barely liked.

Turns out, being “you” beats being cool every time. You don’t care anymore whether people liked you or not. You care more about being yourself.

19. Letting clutter pile up

A cluttered study desk with a laptop, notes, calculator, and multiple screens.
©Tomas Yates/Unsplash.com

Your space looked like a garage sale had exploded. Clothes on chairs, empty pizza boxes, unread books stacked like furniture.

A clean space now feels like a mental reset. Decluttering becomes therapy you can actually see.

20. Thinking that turning 30 meant getting old

A birthday cake with lit candles spelling "HBD" and topped with chocolate pieces.
©Curated Lifestyle/Unsplash.com

You once treated 30 like a looming deadline, like you had to have everything figured out or risk being left behind.

Looking back, your 20s felt more like a training ground, and it actually prepared you for the things that lie ahead. If 30 is old, then your grandpa must be ancient at this point.

Lifestyle Everlane

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About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

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