101 Mistakes You Should Totally Make In Your Twenties
101. Make friends with someone mean, and make fun of everyone else until one day you realize that they’re all having more fun than the pair of you are.
100. Take a job you hate, where the bosses are unfair and the money is bad. Find your best friends in the world while working there and complaining constantly.
99. Kiss someone whose name you don’t know, preferably at a dance club, preferably on the dance floor, and then never talk to them again.
98. Write extremely personal things on the internet that you’ll be able to look back on in 10 years and cringe so hard your insides feel like a trash compactor.
97. “Break up” with your best friend over a really dumb fight and then realize two days later that you aren’t even yourself without them and apologize to them with a series of letters and care packages nicer than anything you’ve ever done for a significant other.
96. Become completely obsessed with someone in a band, show up so early to their show that you have to sit on the sidewalk in the sun and then feel super lame when they show up and see you.
95. Take a job you love and then quit for a really dumb reason like “wanted to spend more time with your boyfriend,” spend the entire summer chain-smoking cigarettes and buying comic books and having sex on his gross carpeted apartment floor and think, maybe once or twice, that it was totally worth the 2K you had to borrow from your parents to get by, until he breaks up with you over the phone.
94. Be so afraid to hurt someone’s feelings that you refuse to break up with them but just silently sabotage the relationship until they do the breaking up, and then in the middle of them doing it become totally heartbroken and emotionally devastated and realize that humans are weird and broken little machines.
93. Laugh at someone’s joke just because they’re pretty.
92. Start a band solely because you have a really good name for one.
91. Injure yourself playing coed recreational beer league softball, never pay the hospital bill and ruin your credit score for the next seven years but feel really tough in the process. Show everyone your scar, until the end of time.
90. Stay up all night hanging out and then go to work the next day, figure out what dying feels like by 3 p.m.
89. Try a bunch of weird diets, decide you’re gluten-free, eat only bread for a week, and then eventually realize that nothing feels as good as pizza tastes.
88. Hurt your mom’s feelings because you’re a terrible monster, look at her face crumble, and vow never to be a terrible monster again.
87. Let your dishes sit in the sink for two weeks, realize when you’re cleaning them that you are a disgusting person. Briefly wonder if you can die from being grossed out.
86. Sleep for 20 hours straight, wake up as tired as it would be if it was 4.
85. Do some ridiculous drug just because it was there, see rainbows on the walls, become really evil, and learn something new about yourself.
84. Look up porn of something really specific and weird, decide after two minutes that the internet is both a blessing and a curse.
83. Try on a different religious identity for a few months, realize that beliefs aren’t like clothes and don’t really work that way.
82. Turn your back on all the music you loved in high school, only to realize around the time you turn 30 that you’ve been a snob this whole time and those were all jams.
81. Try to wear a “hip outfit” and feel completely self-conscious all night long (but you’ll actually look awesome).
80. Borrow money from one of your friends and feel so awkward about it that you actually start using your savings account.
79. Accidentally adopt the cat you’ve been feeding outside your door for the last few months, become overwhelmed by having responsibility for another life, and then slowly, over the course of the following years, grow to truly love the cat and become a more generous and big-hearted person because of him. Have no idea how to afford the vet bills that later result.
78. Become infatuated with your best friend’s boyfriend or girlfriend, keep it a secret for the rest of your life.
77. Question your sexuality at least five times, add letters to the LGBTIA to describe yourself.
76. Cut your own hair.
75. Declare that you “HATE” something popularly accepted as a classic, feel like you’ve really grown as a person, later realize that thing was probably actually pretty good.
74. Hook up with someone you work with, tell yourself it will never happen again, and then watch it keep happening over and over as if you’re watching a TV show and not making actual choices with your life.
73. Get wasted enough to dance with complete strangers.
72. Have sex with your ex. (Warning: probably will be the best sex you’ve ever had.)
71. Go out in a new city and accidentally forget to charge your phone, get completely lost without a smartphone to rescue you, wonder how anyone ever did this before.
70. Have your heart shattered, try to forget how upset you are by going to a party. Proceed to drink at least seven beers, start telling everyone what a good partner you are and maybe cry.
69. Develop an insane, overwhelming crush on someone you barely know, think about them constantly, plan your lives together, and then find out they have a S.O.
68. Take a TON of selfies because they’re the only pictures you think you look good in, post them constantly and allow yourself to believe that people will fall in love with you because of them. Stare at your face on your little phone at night and secretly think that you might actually be one of the most beautiful people on the planet. Feel the precise opposite everytime you get tagged in the background of someone else’s photo, looking like a fucked up children’s painting.
67. Go to Vegas. Things will happen. Let them.
66. Design your perfect “makeover” moment, deciding that if you get dressed up and change your hair enough the person you like will finally see you in a new light; show up and find out they’re not even coming.
65. Waste hundreds of hours on re-watching TV shows you already watched as a teenager.
64. Reach 26+ and start telling people you’re “feeling old,” get major side-eye from everyone you know who is actually over 30.
63. Decide maybe you can make friends with a wild animal, have your first and only rabies scare.
62. Forget to vote, declare that voting doesn’t matter, and tell everyone it was a political decision.
61. Decide you hate everything in your closet because it isn’t you, sell everything at Buffalo Exchange, and then spend the rest of your life trying to find the twin of that one jacket.
60. Wear impractical shoes, summon giraffe vibes.
59. Go out every night for an entire month.
58. Realize that even the best jobs don’t make you that happy and decide you’ll maybe you’ll just get another loan and go back to school so you can stall for another four years. Optional: Actually go back to school, put yourself further in debt.
57. Charge it! CHARGE IT! CHAAAARGE ITTTTTTTT. Literally turn back the hands of time when you realize how much debt you’re in, but once you get there you still really want that fancy TV because nothing can ever really be changed and time was just a construct in the first place. Charge it.
56. Promise your friend that you won’t get crushes on the people they have crushes on, do anyway.
55. Hook up with someone sort of famous, even if it’s just everyone’s favorite bartender or something. Famous enough to brag about it, even though it was terrible.
54. Have an existential crisis in the middle of a hangover, wonder if life is meaningless or if it’s just YOUR life that’s meaningless.
53. Tell someone to “fuck off,” feel HUGE with power.
52. Discover the hard way that you can actually drink too much coffee, contrary to your previously stated beliefs.
51. Get really sick and watch the same movie five times in a row, wake up from your fever with the scenes imprinted in your brain as if they’re real memories.
50. Break someone’s heart, shake and shrink like a potato chip bag in the microwave.
49. Hold someone’s hair while they throw up.
48. Find a job listing that actually describes your real-life dream job, do EVERYTHING in your power to get the job, and then don’t get it.
47. Get genuinely angry about losing your flip-cup touch.
46. Pretend to know a lot about something you know nothing about in order to impress someone, get caught in your lie, and crawl into a hole in the ground from which you will never emerge.
45. Think about cows’ faces while you’re eating a burger, weep.
44. Get into a political argument with one of your best friends at a party, ensure that no one else there will ever want to hang out with either of you again but somehow feel closer and cooler after it’s all said and done.
43. Listen to the same song 100 times in a row, realize later that your listening activity was published to Facebook and that everyone knows how you feel about Katy Perry now.
42. Fall in love with someone who says they “can’t” be in a relationship right now but they want to hook up anyway, hook up anyway, get really upset when they don’t want to be in a relationship. Secretly remember that they told you that all along, but convince all of your friends that you’re right to be shocked and angry. Later, hook up with that person again because despite it all there’s nothing quite like getting to kiss someone you’ve been thinking a lot about kissing.
41. Go skinny-dipping with your friends, feel super weird but then suddenly a few minutes in just stop feeling weird and realize we’re all just humans with bodies and imagine that you’re going to carry this new revelation with you for the rest of your life. (You don’t.)
40. Decide that someone is your “enemy,” talk constantly to your friends about all the things that are wrong with them. When something terrible happens in that person’s life, realize that they were just another person the entire time and briefly see yourself for the demon that you really are before deciding it’s karma.
39. Spend an entire evening just reloading your crush’s Twitter, Facebook, Instagram, and Tumblr pages to see if they’ve posted anything, let hours pass this way until you realize that they must have been out — PROBABLY ON A DATE — and that by now they have gone to bed, emerge from your obsessive daze like someone who just got beat up in a bathroom.
38. Try to learn to cook, burn yourself at least 20 times. Optional: Set fire to your kitchen.
37. Go on a date with a stranger, realize halfway through that it’s not going to work, and concoct a truly elaborate escape plan involving bathroom windows — just like the movies! — before realizing that’s an incredibly mean thing to do and just suffering through the rest of the date.
36. Text someone 10 times in a row, realize what you’ve done, and turn into a small pile of warm pink ashes right on the spot.
35. Read David Foster Wallace for the first time and decide you’d like to write a novel. Participate in National Novel Writing Month, “write a novel” in only the most literal sense of the word, read your own novel a few days after September, and question whether your entire birth was a mistake and/or whether DFW was an alien. Get over it, try again later.
34. Find a song that makes you especially sad and put it on every playlist and mixtape you create because you just love pain, apparently!
33. Do something radically different to your hair, and then do that again, and again, and again, and still expect people to notice and get excited the fifth time.
32. Wear a sexy Halloween costume that’s masquerading as a funny or interesting Halloween costume but is really about looking great, still criticize other people’s sexy Halloween costumes because everyone is a hypocrite.
31. Get creeped out by the accuracy of your horoscope and/or a palm reading, consider making actual life decisions based on what was said because who’s really to say it’s any less arbitrary than any other way you make decisions?!
30. Get into a screaming argument with your significant other in public, get so mad and worked up that you don’t even care that people are staring at you, realize two weeks later that you have no idea what the fight was even about.
29. Decide what “your drink” really is, immediately drink so many of them you puke, and then never be able to drink that specific thing again.
28. Do something you’re really afraid to do, like go on the Tower of Terror or have weird sex, just to prove that you were right all along to be afraid of it and confirm that you will never do that again.
27. “Fall in love at first sight,” except it turns out that’s just lust and most humans are a nightmare.
26. Share incredibly personal emails and text messages from the midst of the most intense parts of your relationship with a group of your best friends, get their opinion and basically have little mini versions of them talking to you in your brain at all times, so you’re never really alone with anyone.
25. Wake up in the middle of the night and try to wake up the person sleeping next to you, when they don’t budge suddenly feel incredibly lonesome and start crying for no reason. When THAT wakes them up, get mad at them for no reason at all.
24. Develop a crush on your married boss or teacher! It’s so dumb that it will remind you how silly you are next time you’re feeling egotistical.
23. Eat an entire pizza. Expand to the size of your entire apartment. Stay in the bathroom for hours.
22. Memorize the phone number of someone you never get up the guts to actually call.
21. Get so messed up that you accidentally throw away some money or shower with your clothes on.
20. Eat a food you’ve always hated by accident and enjoy it and then question whether you’re still the same person that you’ve always been or if it’s possible an alien has entered your body and started animating your limbs.
19. Kiss someone you know is a terrible person, but in the moment when you’re kissing them instantly understand their humanity and everything that led up to them constantly hurting your feelings, like some kind of superhero mind meld. Immediately forget as soon as the kissing stops.
18. Lose an entire week to beer and making out. Call it your lost week and remember forgetting it forever.
17. Actually run into a pole because you’re so busy checking someone out that you didn’t notice it was there.
16. Get drunk by yourself for the first time, wonder if this means something bad, actually just have a good time watching bad TV and trying/failing to read.
15. Hook up with someone you’re not that into just because you’re in an awkward situation with nothing better do, enjoy it anyway.
14. Realize you don’t know what people are supposed to wear to weddings, funerals, or job interviews. Realize once you get there that no one else really knows either.
13. Invent a new abreevs that will annoy the shit out of everyone you know.
12. Watch someone you thought you’d marry someday marry someone else.
11. Believe that a mistake you made is actually the end of the world. No matter what your friends say about how it will be OK eventually and everything is funny someday, no matter how much you assure them you know they’re right, end up at home alone in the dark and feel sure with every little cell in your body that nothing will ever be OK again. Refuse to notice when little moments are actually pretty great, refuse to remember that you felt this way before, just insist, to yourself, that you’re at the bottom of a well you’ll never be able to crawl out of it. Six weeks later, crawl out.
10. Suddenly realize that you’re actually LIVING the only life you have, that the minutes are literally ticking by like a video game, that “The End” will actually happen someday, however far away (or not) that may be. PANIC and make a bunch of these mistakes all at once.
9. Take a job you’re pretty sure you can’t do and that you’re completely intimidated by, DO IT WELL, and then constantly wonder when the other shoe is going to drop.
8. Fall in love with someone who will never, ever love you back.
7. Take that one secret thing that you know about someone who you care for, the one thing that will really, really hurt them, and use it against them in the middle of the worst fight you’ve ever had. Understand fully, for the first time, what “the power of words” means.
6. Live with a stranger, just to have some stories to tell later.
5. Experience a hangover so bad that you wrap your entire head in warm towels while lying on the tile in your bathroom so that you can somehow remain both warm and cool AT THE SAME TIME, which doesn’t actually work at all.
4. Don’t call your mom for a long time, the longest you’ve ever gone without talking to her, and feel a creeping vine like sickness sprout in your chest and start strangling your soul slowly, but defiantly. You can’t figure out what’s crushing your soul and then one day you call your mom and all of your symptoms disappear.
3. Meet your soulmate, but it’s not a cute boy or a pretty girl you want to kiss, it’s just your actual best friend in the world. Spend the next few lifetimes making mistakes with them and wishing that the world was set up so that you could be each other’s first priority forever instead of having to ever think about relationships or jobs again. The mistake is in thinking that it’s not true that the world could go that way.
2. Realize you’ve found “the one,” and spend years of your precious life crafting the relationship you’ve always wanted, putting everything you have into the idea of “us,” and becoming the person who truly deserves this perfect human you’ve finally found. When that relationship ends, pretend for a while that all of those ways that you grew and improved went away when they did, but it turns out that they don’t, you’re still a better person and so they’ll be with you always, in a way.
1. Assume that once you hit 30, you’ll stop making mistakes.