I recently got the type of message that only arrives through social media: a guy named Matt in Seattle tracked me down on Facebook to let me know that he was getting rid of a car I’d sold him 10 years ago. He’d been cleaning out the silver Subaru for the last time before donating it to a women’s shelter, and he’d found nine of my old cassettes. He’d gotten in touch to send me a photo of my tapes, lined up in three rows against the blue fabric of the trunk.

Among those spooled cockroaches were mixtapes from two of my high school boyfriends, both named Greg. Just looking at their handwritten titles was like opening an old photo album I’d forgotten I’d owned. Was there ever a high school mash note as intimate as a mixtape? The Gregs and I, we’d spent hours selecting and recording music, writing out our liner notes, and drawing artwork for these pocket-sized containers of angst and lust. Now that digital playlists are easily swapped and text messages artlessly record our longings, mixtapes are the last 3-D time capsules of the love letters we awkward kids used to craft.

I grew up 20 minutes outside of Portland, Ore., in a development bordered by farms and golf courses. Nearby stripmalls housed adolescent staples: the 7-Eleven we’d spend summers biking to in search of Slurpees, and Pizza Caboose, where the sports coaches I had no desire to play for took their teams for blistered pies. I could’ve cracked my skull apart with the concentration I put into pretending I lived somewhere else.

I took refuge from suburban claustrophobia by discovering new music with my best friend Monica. Her bedroom was my original fantasy portal out of Rock Creek. In grade school we cut out photos of the bands we loved from the pages of Bop magazine and glued them to the wallpaper, covering every inch of space between her bed and the furthest our fingers could reach on tip-toe. We collaged Monica’s walls with pouty New Wave visages, hundreds of yellowing angular haircuts offering a timeline of ’80s fandom.

By the ’90s I pushed open the wardrobe behind the frosty lipstick bands and discovered a new landscape of groups playing all-ages shows in Portland. I’d buy tapes by “alternative” acts like the Dharma Bums, Oingo Boingo, and Material Issue. These were the weirdos I aspired to meet, and to become, and to connect with other teenagers over. I compiled my favorite tracks onto blank cassettes from Radio Shack. The mixtapes were Morse-code messages I traded with other suburban satellites, hoping we moved in similarly strange orbits.

Of course, these curated cassettes were more than just calling cards — they also expressed complex feelings about the recipient. Greg Bobbitt, the older of those high school boyfriends, recently sent me photos of a triple-tape mix I’d made for him, one I’d crafted as we were vacillating towards, as the title explains, “Really Good Friends.” My liner notes, which take up the entire underside of the title card, make me cringe now. Sample lines: “Today is Monday. Monday after I told you everything. Although I want to, I’m not going to write any temporary feelings on this tape. I’m way too confused. This age is hell, but I’d much rather struggle and gain then be sheltered and gain….” And… god, do I have to go on? Mortifying stuff to read. But like a journal, the mixtape is a snapshot of the mercurial emotions I had in high school — about Bobbitt, about any boy I dated, about getting out of Portland. Mixtapes recorded more than just our favorite playlists.

My introduction to Bobbitt was complicated. I’d met him back in ’91, while we were in line for a teen dance club called Quest. I’d arrived drunk on Kool-Aid and Everclear. I proceeded to slap him across the face for making some innocuous joke behind me. Cut to us mashed up against one another in Quest’s arcade room hours later, making out in between my barfing into a trash can, a ridiculous flirtation that was followed by years of adolescent drama and then decades of friendship.

I call Bobbitt, who still lives in Portland, to talk mixtapes after having lost touch with him over the years. He explains that he keeps every correspondence that anyone has ever given him, both written and musical, in a giant Rubbermaid bin. “I never had a journal. I don’t have something that you can look back on where it’s amazing to look at yourself at that age,” he says. “The only thing I have that’s remotely like that are the mixtapes.” He adds that he knows exactly where the four or five mixtapes I made him in high school are: “I wouldn’t get rid of those,” he says.

Bobbitt made the best mixes — double-cassette compilations of the Replacements, Hüsker Dü, Camper Van Beethoven, and other ’90s college rock acts that significantly deepened my musicial appreciation. His tapes also offered me new excuses to leave the suburbs so I could see these bands play live. The cases of these premium high-bias tapes (never the generic bulk brand) would come superglued together, Bobbitt’s handwriting meticulous in part because he only wrote with Uni-Ball fine point pens. He’d make sure the levels were perfect, eliminate any pregnant pauses, and allow every song to come to a complete finish. “I’d do the things that somebody who sequences and masters CDs these days does,” he says now. “The technical side of it was very important to me.”

Of the hundred or so mixes he’s made over the years, “Left of the Dial” by the Replacements was on nearly every tape Bobbitt created. The song’s poetic sentiment (“If I don’t see you again for a long, long while / I’ll try to find you left of the dial”) about remaining in someone’s thoughts through music has always resonated with him, and it’s an apt theme when thinking about mixtapes in general. “That line has always struck me as something I’d like to convey to somebody,” he says. “It’s like, ‘You mean something to me, and if we don’t see each other for a long time, we’ll meet up again someday and it’ll be great.’”

Greg Keefer, my younger high school boyfriend, had long, wheat-colored hair to Bobbitt’s chocolatey bob. Not long after we’d admitted our mutual crush, Keefer was hit by a drunk driver. The car shattered his leg and left him housebound for months, during which time I delivered homemade cookies and mixtapes to his bedroom. I’d hoped my cassettes could compel him to think about me for at least 60 to 90 minutes a day, depending on the length of the latest mix I’d made him.

Keefer was a shy, sweet kid. He says now that he wasn’t the most comfortable teenager. Mixtapes were his way of exposing what he was too timid to say on his own. I’d drive home from his house with the windows rolled down, blasting his favorite power ballad by Alice in Chains, or a spastic punk jam from Jane’s Addiction, feeling caught up in the bombastic emotions he’d expressed on his mix for me. In the end, though, music didn’t save us. We went back to being friends after a just month of making out — from the neck up, so as to not disturb his broken leg.

After not hearing his voice in decades, I call Keefer at his current home in Austin, Tex. He tells me that he also has a box of mixtapes at home, one that’s made every move with him since high school, because they’re mementos that have retained all their meaning. Although not every Keefer cassette contained love songs.

One old girlfriend of his (who later became his wife, then ex-wife) got the bulk of the mixtapes he made. She grew up in a conservative Mormon household where her mom would toss her Beastie Boys tapes in the trash. But Keefer’s tapes would slip in under the radar, shepherding taboo White Lion ballads and Van Halen anthems inside coverless cassettes.

His relationship with this girl was tumultuous, he tells me, and at one point in high school she started dating other people. “That’s when I’d make the ‘I’m pissed at you but I still care about you’ tape, with all the little jabs,” he says with a laugh. Those tapes would always include some Zeppelin, particularly “Your Time is Gonna Come.”

No matter the circumstances, though, making mixtapes was a romantic rush that we just don’t get in a digital age. “At that point in time, no one could communicate better than the artists we looked to and loved,” Keefer says. “Being able to take someone’s work and apply it to someone else in hopes that they have the same connection that you do, that’s such an important part of connectivity.”

Or, to be a little more crass about it: “I know this sounds awful, but I don’t know that I ever made mixtape for somebody whose pants I didn’t want to get into,” says Bobbitt with a laugh. And for the most part, it seems, it worked for him.

In making our mixtapes, some of us were too wordy while others only found courage in the lyrics of others. We each pressed play and record and pause and record and rewound and doodled and listened until, hours later, we had a tender artifact to share with someone about whom we cared deeply. And although I lost my mixtapes in a car I sold to a stranger ten years ago, I appreciate the way those analog ghosts triggered special memories of early, fumbling courtships that otherwise would’ve remained lodged away forever.

I don’t have any way to play cassettes today. So I don’t need Matt from Seattle, who suddenly disappeared from our Facebook conversation, to send those old mixtapes back to me. My current Subaru only accepts CDs, and the floor of my car is scattered with them, including all the blank ones my husband has burned for us over the three years we’ve been together. He sometimes makes mixes, other times burns whole CDs. They come with no liner notes or cases, no sprawling love letters from the music geek I married last year. And yet, I can pick up the one labeled for the band Family Portrait and remember exactly when he Dropboxed me that album, the night after our second date, when I already felt like I might be falling in love with him. It may not be a mixtape per se, but it’s a modern time capsule for this digital era, bringing with it different sorts of memories from left of the dial.

Jennifer Maerz is the former editor-in-chief of The Bold Italic. Prior to that, she served as music editor for The Stranger and the SF Weekly, respectively.