I can remember with clarity the first time I heard Jenny Lewis’ voice — the place, the time of day, what I was wearing. It was during ninth grade, one weekday after school, in my friend Lauren’s basement, when her cool older brother’s cool girlfriend pulled up a Postal Service song and played it through the speakers of a desktop computer. At the time, it felt like Lewis’ voice floated with defiance. Her voice also felt novel, at least then, to me, in 2004. I can say with complete confidence this was the first time I heard a female voice in “indie music” — a phrase I did not know or understand, my main musical epiphanies at that point having come from the hyper-masculine, hyper-mediocre Long Island emo scene, a world where women only exist as mere fan-girls, or cruel song subjects for whiney heartbroken dudes.

Unbeknownst to me at the time, 2004 would be a huge year for Jenny Lewis. Not only was she touring the country as a member of the Postal Service but she also had her own band, Rilo Kiley, and their third full-length was out that year, too. It was called More Adventurous. I latched onto that record hard. I loved every minute of it and expressed that love the only way I knew how: by copying and pasting select lines from SongMeanings.net onto the lines of my AIM profile, LiveJournal, and ‘away messages’ every day. Lewis’ voice was wounded and cynical and just emo-tinged enough to appeal to a Taking Back Sunday-obsessed mall-brat like me. But it was different enough to stretch my tastes to someplace totally new.

Something else I know now that I did not know then is that More Adventurous is a distinctly Mike Mogis record. Mogis was essentially the Saddle Creek house producer at the time; in 2002, Mogis helped to polish up and expand Bright Eyes’ sound from thin home recordings to the lush, moving masterpiece that was Lifted Or The Story Is In The Soil Keep Your Ear To The Ground. Soon he did the same thing for Rilo Kiley.

In total, the credits for More Adventurous include nearly 30 contributors, making for a huger-sounding album than the band’s previous work: 1999’s Initial Friend EP, 2002’s Takeoffs And Landings, and 2002’sThe Execution Of All Things. The main attractions in all previous Rilo Kiley songs were the voices of Jenny Lewis and guitarist/singer Blake Sennett, a fellow former child star whom Lewis dated for years. On Adventurous that remained true; in addition to Jason Boesel on drums and Pierre “Duke” de Reeder on bass, the album also included a whole crew of players on flugelhorn, orchestra bells, clapping, congas, handbells, shakers, timpani, and more, with Mogis himself being credited as playing banjo, glockenspiel, guitar, mandolin, pedal steel, synthesizer, vibraphone, and wurlitzer. “For one of the songs, we wanted doo-wop singers for back-up, so Mike Mogis and I went to the music building at (the University of Nebraska-Lincoln) and asked a professor who we should talk to,” Lewis said in a January 2004 interview with Dailynebraskan.com. “He suggested a group to talk to, so a couple of members came to Presto, recorded the song and then we took them out for tacos.”

Indeed, this record was made with the intention of releasing it with Saddle Creek. But in the end, the band decided to start their own imprint distributed by Warner Bros., much to the dismay of many Saddle Creek fans at the time. “It would have been great to work on the Rilo Kiley record, but there was just some things that we didn’t see eye to eye on,” Robb Nansel of Saddle Creek told Tweed Magazine in 2004. “Some things that they were interested in were not of interest to us, and rather than making compromises that inevitably would make one party feel uncomfortable or the other party feel shorted, the decision was made for them to do the record without us.” Further interviews reveal differences about the band’s interests in commercial radio and music marketing, versus Saddle Creek’s commitment to a community-centric indie approach.

In another life, maybe I would have held this against Rilo Kiley, questioned their motives for wanting to work with a major label, and resented them for abandoning Saddle Creek. But instead, all I can do is wonder if I ever would have heard this record in the first place without it having major-label distribution. More Adventurous deserved to reach such larger audiences, anyway.

Adventurous deserves to be remembered as the ultimate anti-love album of the early aughts, not because it rails with rage or sobs uncontrollably in heartbreak, but for the way it embraces the futility of precious love, laughs under its breath at the ways relationships can ruin our lives in subtle everyday ways, quietly rejects the institution that is marriage.

Full of perfectly story-centered pop songs, Lewis’ words hide from no one in a way that is almost embarrassingly sincere, but she only ever sounds cool and clear and confident. Her attention to dialogue, scene-setting, and developing characters is perhaps a nod to her interest in country and folk music, or maybe a result of years spent working as an actress in Hollywood during her youth. Either way, her sort of poetry is composed of specific moments, memories, friends, quotes, advice, observations, melodrama, and tragedy. It is candid and filterless and real as hell. According to some rumors, Lewis recorded at least one of these tracks in the nude to capture a particular feeling of vulnerability.

The sure and steady-strummed opening track, “It’s A Hit,” is an absolute reminder that this record was created in 2004 when the country was more noticeably being run by the right-wing: “Any chimp can play human for a day, and use his opposable thumbs to iron his uniform, and run for office on Election Day, fancy himself a real decision maker.” It’s dotted with tambourines and shakers, tinged with the slightest hints of anti-institutional thought, even eventually making fun of (and demystifying) artists much like herself: “Any idiot can play Greek for a day, join a sorority or write a tragedy/ and articulate all that pain, and maybe you’ll get paid.”

She paints such an epic tragedy in the following track, “Does He Love You?” chronicling a complicated love triangle, covering every emotion potentially felt by marriage: confusion, cynicism, hope, fulfillment. Lewis has often talked in interviews about her parents’ divorce (they split when she was 3 years old) and the effect it had on her. On this track in particular, Lewis questions whether marriage has any place in her life. She also addresses a friend whose path has diverged from hers in “adulthood”; the friend is now running an antique shop with a baby on the way. When Lewis says, “You’re better off for leaving,” you can hardly believe her. But when she shouts, “I AM FLAWED IF I’M NOT FREE,” it is the ultimate acceptance of the life she’s chosen. It’s one of the record’s highlights.

“Portions For Foxes” is an anthem of total indulgence in messy, sex-centric flings. It is not defeated, or heartbroken. It has low expectations. “I know I’m alone if I’m with or without you — but just being around you offers me another form of relief.” Is its ultimate conclusion — that “we’ll all be portions for foxes” — just a poetic way of saying “nothing matters, everything is temporary”? Perhaps, but Lewis’ sweet voice suggests there’s relief in that.

On earlier Rilo Kiley recordings, Sennett’s voice was more present. On Adventurous, he takes lead vocals just once, for “Ripchord,” and it’s one of the most beautiful and devastating moments on the record, a tinny and spare acoustic number reflecting on the death of Elliott Smith. Rilo Kiley considered Smith a friend; Sennett’s first album with the Elected was recorded at Smith’s studio. A “ripcord” is the piece used to release a parachute while skydiving — it essentially saves you when you fall. But when Sennett utters the line, “Pull the ripcord, the ship has lost its sail,” there is no hope in his voice suggesting the action is saving anyone. The entire song feels like one big breath of desperation, particularly in lines like, “So come on kid, look at what you did, I don’t know if you meant it but you did yourself in … I was even havin’ a good day, when I found out we lost you.” The closing track, “It Just Is,” is also said to be a tribute to Smith: “This loss isn’t good enough for sorrow or inspiration,” Lewis concludes. “It’s such a loss for the good guys.”

As a teenager, I could connect to these songs on an emotional level, but now in my 20s (around the same age as the members of Rilo Kiley when they penned these lyrics), I can understand their intricacies more sharply. Listening from a suburban basement, I mined these songs for the quippy one-liners and unshakeable hooks. I still think those are fine reasons to love a song. But it’s only now that I can fully understand their complexity and the emotional vulnerability it takes to spill out your insides like this.

“I read with every broken heart we should become more adventurous,” Lewis croons on the album’s title track, a reference to a Frank O’Hara poem. The song presents heartbreak as useful in becoming smarter, sharper … more adventurous. The idea that we are “all as numerous as leaves on trees” might be one of the most depressing sentiments to come out of a scene known for fairly depressing work. It also is yet another track that discusses marriage or divorce in some way: “For me to be saved and you to be brave, we don’t have to walk down that aisle,” Lewis sings. “If marriage ain’t enough, well at least we’ll be loved.” Marriage isn’t exactly a particularly unique lyrical theme, but it’s one that will always be universal to 20-something women. There’s a reason why Meredith Graves’ lines marveling at “CHURCHES AND VEILS AND WIVES” resonates so hard, as well as Katie Crutchfield’s pondering over “loveless marriage and regret.”

Jenny Lewis has never outwardly identified as a feminist, and even rejects talking about the subject in interviews. But simply by writing so personally and poignantly, her words have conveyed resonant truths inextricably tied to gender and crippling social expectations. There is a lot of power in that. (“There’s only one difference between you and me/ When I look at myself all I can see/ I’m just another lady without a baby,” she sings on “Just One of The Guys,” a single from her recent solo LP, The Voyager.)

In retrospect, I know my 15-year-old brain was not fully wrapping itself around any of these ideas, or processing most of Lewis’ smart ruminations on love, war, sex, boredom, social expectations, and death when I first heard More Adventurous. But the true strength of in this album, and of Lewis’ songs in general, is conveyed through Lewis’ personality as much as it is through her poetry. Her confidence and candor impacted me as a teenager, and ten years later, songs like “Does He Love You?” and “Portions for Foxes” still do.