Top 10 Hardest Everyday Choices of the 90s

#10: Choosing the Right CD to Bring in Your Walkman

A portable CD player could hold exactly one album, forcing you to predict your musical mood hours in advance. Were you feeling angsty enough for Alanis Morissette, energetic enough for the Spice Girls, or sensitive enough for the Backstreet Boys? Sure, you could carry several CDs, but that meant dragging around a bulky plastic case and accepting that at least one disc would somehow get scratched. For most of the decade, Sony’s portable CD players were branded as the Discman; the company began switching to “CD Walkman” in 1997. Whatever you called it, choosing incorrectly meant listening to the same twelve songs all day or — even worse — being alone with your thoughts.

#9: Lunch Money: Candy vs. Actual Food

Your parents handed you lunch money under the reasonable assumption that you’d spend it on lunch. But the school cafeteria, vending machine, or nearby convenience store offered a far more reckless financial strategy: converting the entire amount into chips, chocolate, and enough gummy candy to compromise your dental fillings. Actual food would keep you alive through afternoon classes, but candy could be used to purchase temporary popularity. The sugar rush made you feel like a genius at noon. By gym class, you were hungry, exhausted, and watching someone else eat a sandwich with seething resentment burning inside of you. But hey, those ring pops had seemed like an excellent investment at the time.

#8: Which Spice Girl to Pick as Your Favorite

Choosing a favorite Spice Girl wasn’t simply about music. The group’s five distinct personas gave fans a choice between Sporty, Scary, Baby, Ginger, and Posh, but friend groups couldn’t tolerate duplicates. If someone had already claimed Baby Spice, you either accepted another role or started a diplomatic crisis beside the jungle gym. Your selection determined whom you portrayed during recess performances, which merchandise you wanted, and possibly what you wore for Halloween. Boy-band fans faced the same problem with the Backstreet Boys and, later, *NSYNC. Choosing a favorite member was effectively a binding contract, and switching up your answer could make everyone wonder what else you’d been lying about.

#7: Spending Your Last Five Dollars at the Scholastic Book Fair

A five-dollar bill at the Scholastic Book Fair carried more responsibility than most adult bank accounts. Or, at least, it felt that way. You could buy the book your parents expected you to bring home, or maybe one of the 62 original “Goosebumps” books published between 1992 and 1997. But then you saw the bookmarks, novelty erasers, and pencils that looked far more exciting than, y’know, the pencils already gathering dust in your desk. Buying a book demonstrated maturity and supported your education. Buying a pointer shaped like a monster claw provided absolutely no educational value but felt urgently necessary. Once that money left your hand, you were left to explain why your “book money” had produced no actual book.

#6: Choosing a Ringtone for Your First Cell Phone

To be clear, this was mainly a late-’90s dilemma, and your choices weren’t studio-quality clips of popular songs. They were monophonic sequences of beeps with such catchy names as “Type 3.” The famous Nokia tune first appeared on the Nokia 2110 in 1994, while 1999’s Nokia 3210 included software that let users compose their own tones. Picking the default meant everyone in the room would reach for their phone whenever yours rang. Choosing something unusual made your phone sound like a microwave experiencing a medical emergency. Either way, every incoming call became a public performance that dragged on until you dug the phone out from the bottom of your bag.

#5: Choosing Between Frosted Tips or a Bowl Cut

The wrong haircut grows back eventually, but “eventually” feels meaningless when school pictures are tomorrow. The mid-’90s offered the increasingly ridiculed bowl cut, while the later part of the decade made frosted tips dangerously appealing. Other options included curtains, crimped hair, face-framing tendrils, the omnipresent “Rachel,” or enough butterfly clips to interfere with local radio signals. You’d bring a celebrity photograph to the salon, sit through an hour of irreversible decisions, and emerge looking only vaguely inspired by the person in the picture. There were no camera filters to preview the result. You simply committed to the look and prayed that everyone at school had made an equally bad series of decisions.

#4: Picking the Right Away Message for AIM

AOL Instant Messenger went live in 1997, and its away-message feature quickly became far more emotionally complicated than intended. You could write “BRB” like a normal person, but that wasted valuable space where you could place a mysterious song lyric, an inside joke, or a suspiciously specific complaint. The ideal message had to make your crush wonder whether it was about them while giving you enough plausible deniability to insist that it wasn’t. Too cheerful, and you looked desperate. Too dark, and people started asking if everything was okay. After carefully announcing that you were unavailable, you’d remain seated at the computer, watching your buddy list and waiting for someone to notice your absence.

#3: Picking the Right Starter Pokémon

Okay, admittedly, you only made this decision once per save file, but still — it followed you every day afterward. When “Pokémon Red” and “Blue” reached North America in 1998, Professor Oak offered up Bulbasaur, Charmander, or Squirtle. Bulbasaur was the practical choice for the early gyms. Squirtle offered a sensible balance of power and undeniably turtle-y appeal. Charmander promised a future Charizard. To make matters worse, your rival immediately selected the Pokémon with a type advantage over yours, confirming that he was a terrible person. Strategy mattered, but so did playground credibility. After all, you were deciding which small, digital animal would become your entire personality.

#2: Choosing What To Rent At Blockbuster

A trip to Blockbuster transformed family movie night into a high-pressure negotiation beneath fluorescent lighting. The unfamiliar movie had exciting cover art, a dramatic tagline — and every possibility of being terrible. The reliable favorite had already entertained you twelve times, but suggesting it again would produce an immediate “We own that movie” from one increasingly impatient parent. Blockbuster, which expanded internationally throughout the 1990s, gave you walls of choices but very little useful information about them. There was no streaming preview or recommendation algorithm. You had the box description, the clerk’s opinion, and maybe a quote from some pretentious film critic you’d never heard of. Choose badly, and the entire household knew exactly whom to blame.

#1: Dial-Up Internet vs. Letting Someone Use the Phone

Nothing tested a family’s loyalty like one telephone line — and several competing priorities. Dial-up internet connected through a conventional phone line, meaning that going online effectively seized control of the household’s communications infrastructure. You might be checking AIM, researching homework, or waiting twenty minutes for one image to load. Meanwhile, someone needed to make a call, expected one, or simply resented the horrible sounds coming from the modem. Worse, someone could pick up another receiver and destroy your connection just as the download reached 97 percent. The internet offered access to the wider world, but only after you convinced everyone in your own house to leave you alone.

Which completely ordinary ’90s decision did you treat like a matter of national importance? Let us know in the comments... assuming, of course, nobody needs to use the phone.