It has been said that there is no person one has less in common with than the person responsible for their 2008 Facebook statuses. Whoever wrote those words, seemingly forgotten yet etched onto the timeline forever, was wild and free. She had a brand-spankin’-new ethernet cord, a grandiose love of the f-word, and a concerning artistic attachment to the lyrical stylings of Ke$ha. She was pre-smartphone, definitively post-AIM, and still blissfully unaware that the internet she’d once played Neopets on was also tracking, logging, and recording her every move. This was a different time, one that sounds fake if you talk about it today.

As I’ve recently been reminded over the course of speaking to millennials about their earliest tech experiences, when we all first got the internet, it came to us not only through a landline … but also via a compact disc sent to us by the America Online corporation, in the mail. In a matter of five years, as personal computers entered our homes, millennials went from scrambling to record the last half of “One Sweet Day” off the radio and onto a cassette tape to being able to download Mariah Carey’s entire catalog (and perhaps some spyware) from Napster and upload it onto our iPods. And then, just as quickly, in the same way that the Swiss Army put a knife, a scissor, and a toothpick into one device, Apple and Samsung somehow took our music, our movies, our GPS, our TiVo; our chat rooms, our emails, our T9 texting; our Neopets, our HitClips, our painstakingly printed porn—and smushed them all into one device that knows our faces, our fingerprints, and our metadata better than we do. But remember when we controlled the metadata? Remember diligently choosing a song for your Xanga? God, remember emails? Long, gorgeous, meaningless email chains with your friends? 

Vote Now in the Final Round of the Millennial Canon Bracket

With impressive speed, millennials learned how to navigate these new ways of accessing the information, entertainment, and self-expression made newly available to us. And to be clear, we weren’t accessing it in a convenient way—but in a painstaking way you had to cobble together yourself, a Discman-to-aux-cord-to-car-cassette-player way you could be proud of. The phones weren’t smart, and hey, maybe we weren’t, either. But the times? They were exciting.

Told by the people who lived it, this is the millennial eulogy for the tech that raised us—it may be gone, but it lives forever in our hearts, in our digital footprints (who knew?!), and in the boxes in our parents' basements full of cords to an old Gateway, where some say you can still hear a Furby chirping today. Let’s recall all of the technological advancements millennials have loved and lost in our lifetime …

Part 1: Meet the Internet

A newfangled computer in 1996
Brian Vander Brug/Los Angeles Times via Getty Images

The internet used to come in the mail. On shiny, gorgeous discs, distributed by the fine people at America Online like street drugs—just a taste to whet the whistle. And once you’d tasted the thrill of A/S/L, there was no going back. The internet was ours. And it was slow. 

Pshhhkkkkkkrrrr​kakingkakingkakingtsh​chchchchchchchcch​*ding*ding*ding*

Sarah Gr. (39, higher education, screen name: bigsy725): I remember my mom trying to describe the internet to me. She had it at work. She was like, “You can just type something in, and it’ll tell you about it.” I typed in “Bugs Bunny” immediately. 

Chase (35, advertising, Texasboi3333): When my dad told me we were getting the internet at home, it was kind of like … well, what are we going to do on it? But once I got on that AOL home page, I was hooked. I was on the internet; I was very on the internet. 

Jarrett (40, film professor, GottaBeMi): AOL used to send these sample CDs in the mail constantly. It'd be 50 free hours, 200 free hours. Just the idea that your internet time was broken down in hours is crazy to think about now. But I remember putting it in the computer and my parents being like, "It's not going to work. We don't have the internet!” And 10-year-old me is like, "It might work.” It did not work. But eventually we got a dial-up modem.

Angela (37, lawyer, Sookes1331): I had older Gen X brothers who set it all up for us, and they were like, "We're surfing the web, and here's what you can do on the web, Angela." 

Lorraine (33, data analyst, LYCowgirl91): We got a Gateway 2000, and all of us crammed around the computer, plugging it into the phone line, hearing it dee-doo-dee-doo, waiting forever for it to connect to the internet. I specifically remember Ask Jeeves was so exciting. You could just ask Jeeves a question.

Caitie (38, contract specialist, qtpie23): If I had done my homework and practiced my piano for the day, I could go on the computer. And there were certain games deemed educational by my parents, like Carmen Sandiego and Kid Pix, that I was allowed to play basically any time. Kid Pix was like Microsoft Paint, but on the Limitless drug. 

Lorraine: Oregon Trail was big, and then we had Backyard Baseball, and there was this Barbie game where you could pick out different clothes for Barbie. 

Davis (45, wine professional, theatrejunky40): We got Mavis Beacon Teaches Typing at home, and I got really good. To this day, I have the world's worst penmanship, so being able to type out school assignments was great. But it actually took awhile before teachers would accept your work like that, which is so funny. They were like, "I don't know about this."

Remember Logging On?

A message to Santa, via AOL
Juana Arias/The The Washington Post via Getty Images

Erin (30, content marketing, Live2Swim722): My earliest internet memories are of getting an AOL email address and emailing pretty much exclusively with my parents. I was sending so many emails to my parents. 

Lorren (37, writer, AngelOfMusic21): I got an email address in the fifth grade. WolfLover, because I liked wolves. Which was a point of contention in our family because my dad was politically opposed to the reintroduction of wolves. He was like, "They're killing all the elk, and I can't go hunting!" But again, I thought wolves were cool. WolfLover@AOL.com was probably one of my first and last rebellious acts … until I stopped being a Republican.

Jarrett: AOL had keywords that you could type in and they would have a little hub, and there was something called Hecklers Online. It was for heckling. We would … heckle someone. 

Chase: I don't have a memory of using the early internet for learning—the internet was for eBaum's World. I was on that website all the time. It was like an online Spencer's Gifts, but with games—eBaum’s World had fun stuff, but then if you went to the back of a store, it was more “Kids can't go back there” type of stuff. 

Haley (28, investigator, PurplePanda07): Nowadays, so much on the computer is a necessity. “I need it to do my billing, or my banking, or my shopping.” But back then, when I would ask, "Can I use the computer tonight?" and my parents asked why, it was like … “To play Club Penguin, Mom and Dad.” I look back, and I feel bad for my parents, who were probably trying to figure out what the heck their kids were on.

Kate (41, social worker, DivaSG): I had a friend whose family were always early adopters, and I have a vivid memory of her coming into seventh grade and saying: "Hey, guys. Last night I was in a chat room with Jonathan Taylor Thomas." And we were all stunned. I mean, she was not. Now, as an adult, I realize, "Oh, you were with some creep.” But we all went over to her house the next day to log into the AOL chat room like, "Maybe JTT is here again." 

Lily (34, education, TigerLily1552): This is why we had to get a second phone line. Because one of us was always on the internet. "Aunt Connie can't call because you're on the internet!"

Kate: I would have friends over, and we would go into chat rooms. We were 14 in Massachusetts, pretending to be 16. "I'm Zoe from Florida." Or “Age/Sex/Location.” 

Jarrett: Oh my God, A/S/L. 

Caitie: I, of course, met some boy who was probably an old man. The classic first chat room experience. Nothing particularly traumatic, just, honestly, early lessons that talking to men can really go either way.

Davis: I actually did meet a girl online really early on. And we wound up meeting later in real life because her parents were planning a trip to Busch Gardens, so she was like, "You can meet us here.” She had no idea what I looked like. I don't think I even knew how to upload [a photo], or if we had the hardware required to do that.

Angela: One thing that was problematic: I think we were catfishing people a lot? My cousins—who are now my very good friends—were older, very cool cousins when I was in sixth grade. And I would take their senior photos and put them on HotOrNot.com.

Meredith (41, compliance, DB8Hottie): We didn't have the same hesitation to, say, try to get into our friend’s AIM account back then. Because, sure, now we know that’s hacking. And that's bad. But back then, it was all just fuckin’ around on the internet. 

Angela: I would get screen names of seniors that I saw in the hallway at my K-12 school and catfish them with my cousins’ photos. I've been a bridesmaid in all of [my cousins’] weddings.

Remember Being a Tech-Toy Parent?

Furby gets his grand introduction in 1998
Getty Images

Lorraine: For those of us who are still chronically online, I think that's a learned behavior. And I think we got it from playing Neopets.

Kali (34, communications, PrincessKamya): All those caretaking, keep-these-things-alive types of games were really big for us.

Lorraine: With Neopets, you had to be at a computer, logging on, and if you didn’t feed your Neopet, or if you went out of town for a week, it would say: "Your Neopets are starving." And you'd feel so guilty, and in order to feed them, you had to go to the soup kitchen, but that runs out after two or three bowls, so then you’d have to play games on Neopets to get Neopoints to be able to buy food to feed your Neopet. We were tired!

Lily: With the Tamagotchi, I remember just being like, "I give up." I put it under a pillow and said, "I'm just going to have to let it die and not think about it because I don't want to do this anymore."

Kali: Tamagotchis were banned at my school, but I was a diligent millennial-child parent. I remember asking my mom to take it to work with her to make sure it didn’t die, and she did. She would clock in at 8 a.m., start her Tamagotchi shift, and keep that guy alive until I got out of school. Raising her child’s child? That’s true love. 

Lily: I was raising a Furby from like 10, waking up in the middle of the night. 

Emily W. (29, tech sales, PupDog0712): I can still feel the Furby fear while I'm sleeping. We need to get our engineers of today onto the Furby, because how that thing still made noise when you took the batteries out is beyond me.

Haley: We had an older cousin who was a little ahead on stuff, and he had that robot dog. My sister and I were like, "Oh my God, I can't believe technology has advanced this far! You are allowed to own a robot dog."

Emily W.: I think my mom used some millennial technology to try to substitute for what we really wanted. Like, instead of a dog, we got the Tekno dog.

Haley: Nowadays, if you had something like that, it'd be like, "Why did you spend $100 on this?"

Emily W.: I was reading it up on Wikipedia. It sold millions.

Haley: I think once you had an awareness that something was a little off here or you’d outgrown something, you outgrew it hard. I'd be like, "Mom, get me more Webkinz!" And then I'd be like, "I'm just actually going to throw all of these out."

Remember Finding Friends on the Internet?

Lorraine: So much of my experience growing up during that time was my obsession with the Harry Potter books. I would go straight to MuggleNet.com; that was the first destination. 

Avi (36, advertising, JoeCool424): MuggleNet was core to fandom ... finding other people who were into Harry Potter to the degree of obsessiveness that I was. It was mostly about theorizing, especially as you got between Books 4 and 5, and 5 and 6. I was like, "OK, cool, other people are doing this, too."

Erin: I spent so much time in Jonas Brothers fan forums in my teenage years. I paid, like, $30 a year to be part of their fan website. You’d pop on there, and there were easily 10 threads about albums, or concerts, or where they had been that day—photos from Just Jared of Joe Jonas and Taylor Swift in New York. 

Lorraine: I was obsessed with The Mole when it first came out, with Anderson Cooper. I was on online message boards, theorizing, like, "Who is the Mole?" Chatting with strangers, just being really excited for it. 

Emily S. (33, music educator, BroadwayBaby91): I was doing a lot of internet research. "Here's what every single mention in the song ‘La Vie Boheme’ means.”

More Artifacts From the Millennial Canon

Erin: One of my most vivid memories from the Jonas forum days was when they put out their album Lines, Vines and Trying Times, and it was the beginning of them not being in this huge moment. I just remember people having meltdowns over the album not selling as well, freaking out, and I got on there and I was like, "It's going to be OK, you guys. We can still love them!" And then that fan forum disappeared, probably before the end of that year. 

Haley: I would go so hard on these new things for months, that once it snapped, I would just feel like, "I think I'm too old for this." You were self-mortified about a thing that no one else even knew about. And then it’s like: "I don't need Club Penguin anymore. I'm released from its clutches."

Erin: It's funny … I remember thinking it was bad back then because I was talking to strangers on the internet. But I was just talking about the Jonas Brothers. Now everybody posts stuff publicly everywhere. 

Haley: If I was my parents, that would freak me out. You have no idea what’s being said online. But they were very measured: "Please just tell us what you're doing so we can try to guide you in the right direction.”

Remember Exploring the Entire World Wide Web?

On the promise of anonymity—and with some slight journalistic proddinga few select millennials have agreed to share what they actually did the moment they got access to the desktop shared by their entire family. That was their time—and these are their stories:

[Redacted]: My family desktop was in our living room, and that was very purposeful so that my mom could see what was going on at all times. But I had a lot of friends whose parents just let them have their computers in their bedrooms. And things were a lot different in their houses. 

[Redacted]: It was very basic. We were literally going to, like, Porn.com.

[Redacted]: The doors to the computer room didn’t lock, so you had to be ready to switch windows. You had to have a plan. The floors were very creaky, so I would have a five-second heads-up.

[Redacted]: Everybody remembers their first dial-up nude image as it downloaded a single strip at a time across the top of the screen. 

[Redacted]: I had a friend over for a sleepover one night, and we realized that if you wrote a bad word with the numbers on the phone—like 1-800-BUTTHOLE, for example—you would get a porn line. So we tried a similar thing with “www.pussy.com.” And what that came up with was just an extreme close-up of a vagina. It was the first time I'd ever seen one, so that's burned into my brain. It wasn't very advanced … just 1-800-BUTTHOLE for the internet.

[Redacted]: My best friend’s family had just gotten a state-of-the-art computer, so we immediately thought, “How do we see some boobs?” We navigated, I believe pretty efficiently, to a photo of a completely nude woman, and because we didn't always have access to the computer all the time, we hit print. It was one of the printers with the roll of paper that had the holes down each side of it, and the computer screen said, “Sending job to printer.” I remember because it said that for the next three days, while my friend’s punishment got progressively worse.

[Redacted]: The very first video that I ever saw, I just remember that it took place in the shower. Because I was blown away that it could happen in the shower. That was never on my list of things … the shower?!

[Redacted]: My friend’s family computer was in her high school brother's room, and naturally, he was like, "I'll show you guys how to get porn." He typed in “Leonardo DiCaprio naked,” and the most rogue, photoshopped naked Leo images appeared. Which we printed. It was crazy. Also, it was not Leonardo DiCaprio. I don't know what that picture was, but it was not Leo.

Part 2: AIM—a Love Story

The good old days of A/S/L
Getty Images

AIM was the rare millennial tech that knew no micro-generational bounds. Seniors in college were as happy to IM with their buddies for hours as seventh graders were. Some even achieved the dream: an away message so good, it forged a love connection inside AIM’s constantly slamming doors, 

Lorraine: I specifically remember going to my dad's office and getting on his work computer and logging into AIM. That is so insane; that would never happen today. But it's just like, "Oh, I got a computer? I got my AIM chat up.”

Jarrett: I would close the doors behind me and just be on AIM. You’d just sit there and wait until someone signed on. It was very loaded to ask someone for their screen name.

Danielle (40, event planner, DestinysBlink827: Whereas everyone today is following everyone's Instagram, you had to at least have a class together to swap screen names.

Jessie (41, jewelry maker, KweenBee35): My very first screen name was KweenBee35 because of that Lil’ Kim song. But regular “Queen” was taken, so I spelled it with “K-W,” and then I went through every single number until I got 35. 

Meredith: I was in debate, so obviously my screen name was DB8Hottie. No numbers. I was the original D-B-8 hottie.

Jarrett: Mine was GottaBeMi, from Garfield—as in the cat. But then NSYNC came out with “It’s Gonna Be Me,” so not only did people think I was an NSYNC fan, but a bad NSYNC fan who got the song wrong. That still doesn’t compare to my now-wife’s screen name: JunkPushur24. She had no clue what it meant at the time. 

Sarah Go. (37, elementary school administrator, JunkPushur24): When I was in middle school, my friends and I would roam the streets of Sherman Oaks, grab an ice cream at Cold Stone, and pop into this vintage shop where I purchased a fateful white tank top with the mysterious image of The Junk Pusher by Robert W. Taylor on it. 

Jarrett: I guess she thought the name meant, like, junk in the trunk? Or maybe she just thought it meant garbage?

Sarah Go.: I had no idea what it meant, and I didn’t look into it. And that is how I became JunkPushur24—because regular JunkPusher24 was already taken. Interestingly, I never got any weird solicitations with that screen name. Because I guess the internet was just a purer place back then. 

Avi: I had a Snoopy backpack that just said "Joe Cool" on it, and so my first AIM screen name was JoeCool424. Because telling people exactly what your birthday is also a really, really smart idea.

Danielle: This is really sad. The reason I know my earliest friends' birthdays so well is that all of their birthdays were in their AIM screen names.

Mike (40, content creator, MZman7): I don't remember much about the internet until AIM—and then I remember being on the computer a lot. Just figuring out how many different Hoobastank lyrics I could fit into an away message.

Jarrett: The away message was a big thing. The first time I saw a friend do that, I was like, "How did you make it do that?" I did lots of quotes, like from Scrubs or Ace Ventura.

Danielle: I don't think kids today could possibly understand the importance of that sound you could set for when your crush signed on. The thrill of IMing someone from calculus class and unexpectedly developing a rapport.

Angela: I remember being at someone's house and seeing who their buddies were and being like, "Oh my gosh, you have his screen name. Whoa."

Lily: My now-husband and I first met over AIM our freshman year of high school. He was TexasBoi3333, because he had just moved from Texas to Missouri. 

Chase (TexasBoi3333): I honestly can't remember how I first got Lily’s screen name. 

Lily: I do know that he was the new guy in town—the Texas B-O-I—so everyone wanted to talk to him and get to know him.

Chase: We talked all the time. I can't even remember texting with Lily—it was just always AIM. You were essentially just at your computer from, I don't know, 7 to midnight every night, talking on AIM.

Lily: I’d go away and put up an away message to make him think I was so busy, and he’d change his background to something he thought I liked. All those different things just felt so crucial. And now I guess that’s like what texting is for teenagers.

I don't think kids today could possibly understand the importance of that sound you could set for when your crush signed on. The thrill of IMing someone from calculus class and unexpectedly developing a rapport.
Danielle

Meredith: College AIM was very different from high school AIM, though.

Danielle: We were making plans on AIM.

Mike: I remember the girl that I was dating … I still remember her sending an IM, like, "Hey, my roommate's gone."

Kate: College was when you could finally leave a Dave Matthews Band away message up all day without it taking up the phone line.

Danielle: And you had to put up lyrics that were just cagey enough. You were looking for someone to be like, “Oh my God, it's a damn cold night? And she’s trying to figure out this life?!

Mike: I was at the very beginning stages of dating someone, and she had lyrics from a song in her away message, and I had lyrics from a different song by the same artist in my away message. And, within an hour, her ex confronted me in the dorm. I didn't know I was doing it at the time, but I gaslit the fuck out of that guy. I was like, "Dude, are you serious? I just like this band, bro, what do you mean?" 

Jessie: I honestly don't remember what I did on my laptop besides instant messaging. Because it was so important for us. AIM is how you found out what people were doing. 

Mike: In an away message, it was: "Noon to 1, I'm in biology, then I'm going right to lunch, and then 4 to 6 in the library." Now I know, that’s so unwise! Here's where I'll be every single hour of the day, so feel free to come find me and rob me. But I did want people to find me.

Jessie: Here's the funniest part. You know how AIM would tell people how long you’d been idle for? On a Saturday night, people would put their plans in their away messages, then head to the bar. And then if someone was still idle on Sunday morning, you'd be like … "Oh, they hooked up with someone." And then that person would go home, check their friends’ away messages and see, "Oh, that's where everyone's having brunch.”

Danielle: I remember being so sad once we graduated and realizing, like, “Oh, we're done with AIM.” That's when Facebook started becoming a thing, and then we all got iPhones … and that was the death of AIM.

Part 3: Call Me, Beep Me, If You Wanna Reach Me

Paris Hilton models her flip phone in 2003
Getty Images

Before there were smartphones, there were flip phones, brick phones, keyboard phones, and ringtones. All colorful packaging for an, at times, intimidating device that millennials used with increasing confidence as time and technology—and free nights and weekends—rolled on.

Kate: My high school boyfriend—not to brag—had a pager. I used to page him from my house phone, and then I would immediately dial 1-800-MOVIEFONE so that when he called me back, the house phone wouldn't ring because we had call-waiting. So that was our patented pager system for late night calling: No one's phone was ringing, and my parents were none the wiser.

Davis: I had a pager when I was 15, and I felt like the coolest thing alive. Even though I had absolutely no reason to have it.

Kate: Why did my boyfriend have a pager? He wasn’t a drug dealer. I don't think?

Davis: There are certain things we've phased out that just were cool. Everyone misses being able to snap a flip phone shut when you’re angry.

Jarrett: I got my dad's old Motorola StarTAC, but it only worked when it was plugged in. So it wasn't really a cellphone. I saved up money and bought a tiny red Nokia that had Snake on it. 

Sarah Gr.: I was so jealous because everyone had the Nokia. My parents got me a Kyocera.

Angela: My friend and I went through this phase where we were constantly changing our home answering machines to us singing "MMMBop” and the Seinfeld theme song, and my dad was like, "Angela, you can't keep doing this, I have patients that call me here!" So they got me my first cellphone, and it had no minutes, no texting—nothing. They were like, "Do not use this unless you're being abducted."

Erin: I had a Juke. The phone that flipped open and then it was tall and thin, like a ruler. Nate Archibald had one in Gossip Girl, which made me feel really cool … until mine got stuck in the upright position and wouldn't close. I couldn’t fit it in my pocket. 

Lorraine: I dropped my flip phone so badly that the screen flipped upside down and backwards. And I wasn't going to get a new phone because it was my fault I dropped it. So I just learned to read upside down and backwards.

There are certain things we've phased out that just were cool. Everyone misses being able to snap a flip phone shut when you’re angry.
Davis

Remember Starting to Actually Use Your Cellphone?

Davis: It felt so cool to be able to get in touch and not have to worry about just running into each other on the quad or whatever. But in the early days, you still had a real reason for calling. Like, "We're going to go see this movie. Do you want to join us?"

Lily: Just having a cellphone and being able to communicate with my cousins who didn't live close by, that was big. I can just … talk to them now. And my mom doesn’t even know I’m talking to them.

Jarrett: The first person who ever texted me, I was like, "How did you send me this message? How did this happen on my cellphone?” Texting just wasn't a primary form of communication. We still had T9. 

Avi: There's a reason we generationally developed emoticons and short-form abbreviations. We had limited characters!

Kate: I had a roommate after college, like 2005, 2006, and she was the first person I knew who was a big texter. I was like, "You must be made of money." 

Lorraine: We had to have this big family meeting where I got called out because I had sent way too many text messages and it was going to cost so much money. After that I was like, "Guys, I can't text anymore. I can't do it."

Evan (39, web developer, CookingWithPunk): I just told people not to text me, and no one really questioned it for a couple of years. You still picked up the phone and called everybody all the time. 

Jon (38, media producer, HardknockJayZ): That made ringtones fun, especially the midi ringtones, before we could use the actual songs.

Lorraine: I definitely had the digital version of Kanye West’s “Gold Digger” as my ringtone. I think I spent 99 cents on that.

Jon: In the movie Orange County, Jack Black yells, "Shaun, pick up the phone!" So my friend Sean took that clip and made it his ringtone for years. 

Kali: In Canada, I didn’t have access to the T-Mobile Sidekick like Summer Roberts, so that's how I ended up with my weird horizontal phone that had a big keypad for texting. But I loved it. I loved that phone. 

Erin: Everyone wanted the LG Chocolate—it slid up, and they had such good colors.

Caitie: I refused to get a cellphone for as long as I possibly could, but finally, my roommates were like, "We can't keep having a landline, Caitie." And by then, everyone had a BlackBerry.

Remember BBM?

Kim Kardashian at Verizon Wireless’s exclusive launch party for the BlackBerry 8330 Pink Curve in 2008
Getty Images

Avi: I couldn't tell you how I convinced my parents sophomore year of college that I socially needed a BlackBerry—but I did.

Kali: BBM swept our school.

Mike: I remember it being very difficult to add somebody's BBM. I think you needed a pin number that was 10 digits, and you had to go to a specific place to find it.

Jessie: At my first job after college, they asked if I wanted a BlackBerry for work, and I was like, “No, I do not!” I didn’t want to email on my phone?

Kali: BlackBerry is an enterprise tool, by the way. I don't know why, at 19, we were all BlackBerry secure. But you'd be exchanging codes with people, and it was like … that is how you communicated. 

Meredith: I had the Samsung BlackJack, which was BlackBerry adjacent—all one screen, full keyboard. And Perez Hilton loaded just fine.

Jarrett: I had a BlackBerry for a year in 2008 before I went full iPhone, and that was the first time a cellphone really changed the way I talked to people.

Avi: You got the BlackBerry for the full keyboard. Because all the things we now do in group chats used to all just be email chains. I was glued to the email on my BlackBerry.

Jessie: Oh my God, we used to email so much. In college, we were drunk emailing. That used to be a thing—people would come home from the bar and email their friends. That was the funniest shit. 

Kate: One of my best friends married a guy she met in college, and for her bachelorette party, we printed out all of the emails of her being like, "Ryan and I stayed up so late last night cleaning the apartment after the party!" It was sweet to have that little record. Almost like journaling with a group of your friends.

Avi: It was the time of "Here's a seven-paragraph update on my life" emails. Was it ever really coherent? No. Did I think I was Carrie Bradshaw? Sure!

Lily: I remember driving to a football game, being on my boyfriend’s BlackBerry, and we were looking up song lyrics—probably High School Musical—and it was just like, "Oh my gosh. I am looking up lyrics in a car. How does this even happen?” 

Part 4: Burn, Baby, Burn, Music’s Gone Viral

A whiz kid at work on his control board and CD player setup in 2000

With whispers of the recording industry suing suburban kids in abundance, millennials boldly—and, sure, often illegally—dipped our toes into the magical world of digital music.

Jessie: I used to try so hard to make mixtapes. Keeping a tape in my little boom box, and then when a song I liked came on the radio, I had to run over and hit record. I'd always miss the beginning—but that was the only way to keep the music that you wanted to hear.

Mike: I would be playing basketball in our driveway, and you'd have to rush over and press play and record at the same time. I’m sure I ruined countless tapes just getting 70 percent of “Gangsta’s Paradise.” 

Kali: I used to write down lyrics from songs that I liked and put them in a little book. Because we didn't have the internet! I would record them on cassette tapes and play them back so that I could make my own song booklet for the Destiny’s Child album I didn’t have. It was just about coming up with ways to access the information you wanted.

Jarrett: I got a boom box for my birthday one year, and that started the CD era. The first three CDs I had were Boyz II Men, Alanis Morissette, and the 1996 Grammy nominees, which was a banger. No skips. 

Lorren: I had the stereo that had three CD changers, and my mom thought it was so ugly, but it was so cool to load in three CDs. I spent all my money on CDs.

Mike: The first two CDs I got were from my aunt for Christmas. And the only reason I remember that is because it was these two CDs: Jewel’s Pieces of You and P. Diddy’s The Saga Continues…

Danielle: Maroon 5 came to my college my freshman year, before they were big, and they gave everyone Songs About Jane on CD. There were “She Will Be Loved” away messages for the entire spring. “Beauty queen of only 18” in so many AIM profiles.

Kate: I had that Velcro thing you could stick the Discman to your hand with. And I would run with the foamy headphones soaking up sweat, and this huge thing on my hand … 

Davis: We had these cassette aux cord connectors so you could play your portable CD player through the tape deck in your car ... 

Kate: It skipped all the time. But I did not have CD-player-in-the-car money to spend!

Lily: All my CDs were up in the visor sleeve, and I remember I would turn too fast and they would just go flying into the passenger seat. 

Sarah Gr.: We talk about how distracted teenagers now are driving with their cellphones. But when I was 16, I had the six-CD changer with the faceplate that would pop off. You're trying to change your CDs, and you're holding a printed MapQuest.

Remember Burning CDs?

Jessie: My older brother used to burn me warm-up mixes for my soccer games. He discovered how to record himself onto the CD, so he would do it with an intro: "This is DJ Chris!” I still don't really know how he did that. 

Sarah Gr.: I remember the first time we got a hold of a CD burner, and it was like: "This is peak technology. I never have to buy a $20 CD again!" Which now, in hindsight—that was pretty messed up.

Avi: I corrupted a hard drive or two as an early adopter of Napster. Reminder: Not all files on the internet are good.

Meredith: You would find a file that would be like, “This is Jimi Hendrix playing with Dave Matthews, plus John Lennon.” Which didn’t even make sense historically, but you’d download it, and just: Russian spyware.

Sarah Gr.: It could be the song you were looking for … it could be a porn. It could have been anything.

Emily W.: LimeWire was on the family desktop—and LimeWire killed the family desktop.

Kate: Everything I downloaded from LimeWire was just a little off. I had a version of “I Believe I Can Fly” that was from some radio telethon, so it just had a part with a woman talking, like, “We're so blessed to have this in our family,” and that was my version. If I heard that now, I think I could do that woman’s part, word for word. 

Lorren: Sometimes it still bugs me because when I look up a song on Spotify, I'm used to whatever weird version I had on Napster.

Davis: On Napster, I could explore things I’d only heard about. It was like, "Would I like jazz? Let's listen to Miles Davis or John Coltrane and find out." And I know it did a lot of bad things for artists in the way that they get compensated—and I do think that artists should be paid. But it also really democratized the way that you could discover new music and share things with people. 

Lily: I remained terrified that I was going to get caught by the police for illegally downloading a song on LimeWire, though. And that was going to be the end of me.

Jon: I had a CD label maker, so it could sort of look legit. A lot of Microsoft clip art band logos.

Lorraine: A sibling would give me a burned CD of just the most random music you've ever heard every year for my birthday. I’d get pumped jamming to, like, the Survivor intro song. 

Danielle: I loved crafting the order of the songs, writing them on the CD in Sharpie …

We talk about how distracted teenagers now are driving with their cellphones. But when I was 16, I had the six-CD changer with the faceplate that would pop off. You're trying to change your CDs, and you're holding a printed MapQuest.
Sarah Gr.

Jessie: I liked that burned CDs were limited. You could only do your 15 to 18 songs. Playlists became overwhelming because you never had to stop adding songs.

Davis: I think Hitchcock said something like, “If you want to see an artist at their best, give them boundaries.” I know times when I pulled a song off a mix because it was too long and put something else on instead—and that was the song that someone responded to.

Danielle: What I really liked about it is that you could mark what was going on in your life when you made a mix CD. You’d see the date on it and be like, “Oh, I was going through a breakup” or “I had a crush on so-and-so.” It could put a musical time stamp on what you were feeling in that exact moment.

Kali: That's my biggest regret in life: In a Marie Kondo fugue state, I threw out all of my burned CDs. 

Remember—and I Promise This’ll Be Quick—HitClips?

Gabby (30, public relations, blabbygabby916): Nothing screamed “I love music” more than having keychains the size of a Scrabble tile playing 60 seconds of “Bye Bye Bye” or “Oops I Did It Again” over and over again. 

Erin: I loved my HitClip collection. I kept them on a carabiner and went through them all on the bus ride to school.

Haley: I got the Michelle Branch HitClip, and I was like, "My life has transformed. Thank you, Mom and Dad, for buying me this wonderful gift where I can listen to [60 seconds] of this song over and over.” 

Gabby: Having more than two HitClips was a distinct socioeconomic marker. Also, these things only came with one headphone that produced the sound quality of a conch shell.

Haley: It was so impractical, and I remember even soon after getting mine being like, “This is going to be irrelevant so soon.” But everyone always wanted music you could walk around with.

Gabby: The original iTunes …

Remember iPods?

Steve Jobs presents the new mini iPod at Macworld in 2004
Getty Images

Caitie: I remember reading about iPods in the newspaper. I was like, “These are coming, I have to have it.” I took the newspaper clipping to my parents, and I think they were excited I was doing engineering in university, so my iPod was like a reward.

Lorraine: But then the problem with getting an iPod is then you had to buy the music. So it'd be, like, every once in a while I'd buy a new single, and I'd just listen to that forever. “That Was the Worst Christmas Ever!” by Sufjan Stevens was the free iTunes download one week. He's my favorite artist to this day.

Erin: I would get iTunes gift cards for my birthday and then be rationing them until the next birthday. For a certain era of time, getting [a kid] an iTunes gift card … that was a sure thing. They were going to love it.

Mike: I remember I had to fly somewhere after getting the very first iPod and freaking out because I was like, “I didn’t turn it off, what if it gets scrambled going through security?!” But no one knew. We’d only had them for like a week.

Jarrett: My first one was one of the skinnier ones that still had a dial on it, and I'd load that thing up and just roam around between classes. 

Sarah Gr.: I had the red version, which was some partnership with a charity. I’m sure I saw it on, like, Oprah's Favorite Things.

Haley: For Christmas one year, my sister and I both got iPod Videos. It propped up on an alarm clock that connected to the iPod and played your music in the morning. I had “1234” by Feist on there, and if anything reset in the middle of the night, that song would automatically play. I heard “1234” so many times. And the music video.

Haley: I was legitimately so scared of the concept that you shouldn’t use your phone on flights, I still used my iPod Nano up until just a few years ago. I was like, "Guys, how about we follow directions and stop trying to use our phones, huh? I have Ed Sheeran's Divide fired up right here!”

Kali: I'm a Virgo. I'm a super-organized person, so my iTunes had to be pristine. I can't even imagine people doing that now. Going on Google or Yahoo or Jeeves and finding the right album art and making sure it's pasted in there.

Jon: I know there's that popular meme these days that’s like, “Today's youth will never know that these were four different bands,” and it's Death Cab for Cutie with the f capitalized or lowercase in four different ways.

Mike: This dude named Brian who lived on my floor introduced us all to MyTunes. It was literally the same setup as iTunes, except rogue—it would sync everybody's iTunes in our dorm, so you could access and download everybody's stuff.

Kali: If How I Met Your Mother was airing, you could go and download it off DC++ that night. It was definitely illegal, now that I think about it. 

Mike: I'm sure someone knows my Social Security number because of that, but I was 19, and that’s how I was introduced to Death Cab. So I thought sharing music was cool as hell. Thanks, Brian.

Part 5: Media Is Social Now

The Myspace home page in 2006
Adrian Brown/Bloomberg via Getty Images

Lorraine: I don't know if I ever actually posted on Xanga, but I had a crush on this guy who was a few years older than me, and I would stalk his Xanga and read it every day. Which is so creepy. But it's like … you didn't realize when you were posting all this stuff, there's some middle school girl who's going home every day to read what you put on the internet before she logs into Neopets.

Emily S.: I was always so jealous of how other people would curate these blogs with all these cool photos. If I could just take a really 2004 aesthetic picture of myself and edit it in black and white with a Fall Out Boy lyric on top, that was enough for me. 

Meredith: Music was very important to me, so switching up my song on Myspace was very important to me. Of course it was the Shins song from Garden State at some point.

Lily: What was that Kelly Clarkson song? “Breakaway.” I just remember hearing that on the radio in the car and being like, I have to put this on my Myspace.

Lorraine: But Myspace was also stressful because you had your Top 8. I don't know if ranking our friends was a thing before that time, but I wonder if it might have irrevocably altered our view of friendship forever? I guess we’ll never know!

Angela: I started following some emo stuff on Myspace my senior year and ended up meeting a boy who went to a different school. Over Myspace, he told me, “I deal bud,” and I thought he was talking about Bud Light because … you know, people sell beer in high school, maybe? So I was like, "OK, that’s fine!” But it turned out he was a full-fledged drug dealer. 

Davis: I remember a buddy of mine, his quote that he had on his MySpace was “The first thing I do is turn off your Myspace song.” And I was like, "That's so true." And I think that was the beginning of, at least for me, social media starting to make us much more self-aware. Because he pointed out to me that he turns this thing off because it’s annoying, and I realized I did the same thing. Then you start to think, “Wait … who am I annoying?”

Haley: I finally made a Myspace in the eighth grade, when I was allowed to, and immediately everyone was like, "We're getting on Facebook.”

Remember Facebook?

Early Facebook denizens in a state of awe in their Boston College dorm
Michael Fein/MediaNews Group/Boston Herald via Getty Images

Jessie: I got on Facebook very early because I went to Yale, and one of my high school friends went to Harvard, so he was like, "Oh, there's this new thing here.” 

Jarrett: It expanded to my school, and I remember going home for spring break and explaining to my parents what Facebook was. “It’s like … a yearbook … where you can go and … look at people from elementary school?”

Jessie: It was awesome early on because it was very limited. We used to post the most inappropriate, embarrassing photos all over the place. It was mostly friends on it, so you didn't have to worry about people seeing your content.

Jarrett: But then it was “What are the social norms of friending somebody? I haven't talked to this person since elementary school. Is it weird?” I remember the day that statuses came out, and it felt like a weird invasion of privacy at the time. Why do you want to know what I'm doing? But also, what do you tell people you’re doing?

Meredith: Just such an amazing, unregulated time. My profile picture was of me doing a keg stand. My best friend, who's just a nice, normal, professional gal, hers was just her hitting a bong. We were loose and lawless and exactly the stereotype, the 100-picture albums on the night out with the catchy slogans.

Danielle: Every Sunday at 6 o'clock, I would plug the camera in, look at every single photo. I would really try to cultivate, like, strive for continuity or something. First album: “Just hold me close, boy.” Next album: “’Cause I’m your tiny dancer.” And I thought that was really ... I don't know.

Kate: “The Party Don't Start Till I Walk In,” but it was just 40 photos of seven us playing beer pong in a dorm.

Avi: I think the genius of Facebook was that it felt curated—it let you express yourself through the content you were posting. 

Danielle: I probably was a huge try-hard. But you were somehow in control of that Facebook narrative and what you were willing to post on there. We didn't have any idea what our digital footprint would be, and our parents weren't on it—so it was just this new place for young people to express themselves.

Meredith: I love to read what people put as their favorite music and favorite movies. I took that very seriously, and I read other people's as “this is a part of their soul.”

Avi: I'd say the last time when Facebook was pure good was just after the initial introduction of the News Feed. 

I miss … chance. The ability to get bored at some point. The romantic part of it and the crappy part of it.
Davis

Jarrett: There’s a famous tweet that’s like, “There's no one I have less in common with than the me that was posting on Facebook in 2009.”

Kate: There’s a Facebook status I made in, like, 2011 that still comes back to haunt me every year: "I'm so excited that the next disc of Gossip Girl just arrived from Netflix."

Haley: Sometimes I wonder, "How much should I scrub my digital footprint?" Because it wasn’t anything that bad. My Facebook is embarrassing. My YouTube is embarrassing. I had a Tumblr in high school, and it had One Direction fan fiction on it. Do I delete that? How do I even find it again? I don't know if I can.

Kate: I tell my kids now, "You guys have it so good.” I couldn't demand a song in the car. I didn't even know any songs. But they can name a song, and I’m like, “Here you go … “California Gurls” by Katy Perry. Again.

Lily: Life360 is great, and being able to know where our kids are is great. But it also takes away some of the ... I don't know. It's OK if they get into trouble.

Meredith: I loved forgetting—I mean, truly forgetting, and leaving my cellphone at home for the whole night.

Davis: This sounds weird, but I miss … chance. The ability to get bored at some point. The romantic part of it and the crappy part of it.

Danielle: You know what I miss? I miss talking on the phone. I liked talking on the phone.

Evan: That’s one where the only barrier is me, but … I am a little nostalgic for calling your friends and not having the excuse not to do it.

Kate: I had a best friend I saw all day at school, and we would still hop on the phone as soon as we got home and just chat about the day.

Davis: I’m definitely one of those annoying people of my generation who still just really loves a phone call.

Evan: My good college friend, for years, was one of those guys who would just call you out of the blue, and that was how we caught up. And in 2020, we probably hadn't talked in a year or two, and then he just up and called me. Out of the blue. And that ended up being a week before he passed. And it just feels so lucky. Sometimes I wonder, “Man, what do we lose out on by not making sure to call our friends every once in a while?"

Jodi Walker
Jodi covers pop culture, internet obsessions, and, occasionally, hot dogs. You can hear her on ‘We’re Obsessed,’ ‘The Morally Corrupt Bravo Show,’ and ‘The Prestige TV Podcast,’ and yelling into the void about daylight saving time.

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